Chemical and Pharmaceutical Bulletin

Catalytic Reduction of Heterocyclic Aromatic Amine Oxides with Raney Nickel. I. Reduction of 4-Substituted Pyridine 1-Oxide Derivatives.

Eisaku Hayashi, Hiroshi Yamanaka, Kazuko Shimizu

1959 Volume 7 Issue 2 Pages 141-145
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.141

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Catalytic reduction of various 4-substituted pyridine 1-oxides in neutral medium, with Raney nickel as a catalyst, was carried out at ordinary temperature and pressure. It was thereby found that N-oxide group in these compounds was selectively reduced, irrespective of the substituent in 4-position, and the products were obtained in a good yield of 85∼98%. 4-Nitropyridine 1-oxide afforded 90% of 4-aminopyridine in acetic acid medium and 4-benzyloxypyridine 1-oxide afforded 93% of 4-hydroxypyridine in one step when reduced over a mixed catalyst of palladium-carbon and Raney nickel. It was considered that this process of reduction is the best method for laboratory preparation of 4-substituted pyridines.

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Catalytic Reduction of Heterocyclic Aromatic Amine Oxides with Raney Nickel. II. Reduction of 4-Substituted Quinoline 1-Oxide Derivatives.

Eisaku Hayashi, Hiroshi Yamanaka, Kazuko Shimizu

1959 Volume 7 Issue 2 Pages 146-148
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.146

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Quinoline 1-oxide and various 4-substituted quinoline 1-oxide derivatives were submitted to catalytic reduction over Raney nickel as a catalyst and results obtained were similar to the case of pyridine derivatives described in the preceding paper. In all cases, compounds were reduced smoothly and in a good yield. In the case of 4-benzyloxyquinoline 1-oxide, the first mole of hydrogen is absorbed rapidly while the next mole of hydrogen is absorbed very slowly, and 4-benzyloxyquinoline 1-oxide is reduced to (X) via 4-benzyloxyquinoline (XIII). This is somewhat different from the behavior of 4-benzyloxypyridine 1-oxide to catalytic reduction over Raney nickel.

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Catalytic Reduction of Heterocyclic Aromatic Amine Oxides with Raney Nickel. III. Reduction of Hydroxamic Acid-type N-Oxides.

Eisaku Hayashi, Hiroshi Yamanaka, Takeo Higashino

1959 Volume 7 Issue 2 Pages 149-151
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.149

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In the catalytic reduction of hydroxamic acid and compounds possessing hydroxyl adjacent to the N-oxide group and forming a hydroxamic acid-type structure, Raney nickel catalyst was found to act specifically in severing the nitrogen-oxygen bond. 2-Hydroxyquinoline 1-oxide, 4-methoxy-and 4-ethoxy-2-hydroxyquinazoline 1-oxide, and benzohydroxamic acid were deoxygenated forming 2-hydroxyquinoline, 4-methoxy- and 4-ethoxy-2-hydroxyquinazoline, and benzamide. In 4-benzyloxy-2-hydroxyquinazoline 1-oxide, the reduction of benzyloxyl group preceded the reduction of N-oxide group and 2, 4-dihydroxyquinazoline was formed via its 1-oxide compound.

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Reaction of 4-Alkoxyquinazolines with Organic Peracid.

Hiroshi Yamanaka

1959 Volume 7 Issue 2 Pages 152-158
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.152

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Reaction of 4-alkoxyquinazolines (II) with perphthalic acid afforded, besides the objective 4-alkoxyquinazoline 1-oxides (III), 2-hydroxy-4-alkoxyquinazoline 1-oxides (IV) as a by-product, formed by oxidation of 2-position. (III) was hydrolyzed to 4-hydroxyquinazoline 1-oxide (V), methylated, and catalytically reduced to 3-methyl-4-quinazolone (VII), whose identification by admixture with an authentic specimen proved the original compounds to be the 1-oxide. The structure of (IV) was also proved by its methylation followed by catalytic reduction to form 4-alkoxy-2-quinazolone (IX).

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Catalytic Reduction of 4-Benzyloxy-6-methylpyrimidine and Related Compounds.

Hiroshi Yamanaka

1959 Volume 7 Issue 2 Pages 158-161
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.158

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Catalytic reduction of 4-benzyloxy-6-methylpyrimidine 1-oxide in methanol over palladium-carbon resulted in the formation of 6-methyl-4-pyrimidinol via 4-hydroxy-6-methylpyrimidine 1-oxide. The use of Raney nickel as a catalyst in this case afforded 4-benzyloxy-6-methylpyrimidine and this is a new type of reaction not recorded in past literature.

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Infrared Spectra of Pyrazine-and Pyridine-carboxylic Acid and Their Derivatives.

Shigeru Yoshida, Motoji Asai

1959 Volume 7 Issue 2 Pages 162-171
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.162

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Infrared absorption spectra of pyridine- and pyrazine-carboxylic acids have following characteristic absorptions. 1) There are broad absorption bands with peaks at 2450 and 1900 cm^-1. The former shifts to around 1900 cm^-1 by deuteration but the latter does not. 2) Absorptions for O-H in-plane deformation and C-O stretching vibration are present at 1340∼1300 cm^-1 and 1310∼1260 cm^-1, and shift respectively to 1360∼1340 cm^-1 and 1080∼1020 cm^-1 by deuteration. 3) There is no absorption band for O-H out-of-plane deformation and that for [chemical formula] is present at around 700 cm^-1. These characteristic absorptions can be explained by the structure (II) with intramolecular hydrogen bonding for nicotinic and isonicotinic acids, and the structures (VI and VII) with intramolecular hydrogen bonding for picolinic and pyrazinic acids possessing a carboxyl in the position alpha to ring nitrogen. The hydrochloride of pyridinecarboxylic acids and 2, 6-disubstituted isonicotinic acid derivatives possess the structure (II) same as that of ordinary carboxylic acids.

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Studies on Thiophene Derivatives. II. Optical Resolution of 3-Piperidino-1, 1-di (2-thienyl)-1-butene.

Ryuichi Kimura, Takahiro Yabuuchi

1959 Volume 7 Issue 2 Pages 171-174
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.171

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Optical resolution of 3-piperidino-1, 1-di (2-thienyl)-1-butene hydrochloride and hydrobromide, which had interesting pharmacological properties, was carried out by the preferential recrystallization method, because these could not be resolved by a method for diastereomers. Thus, specific rotation of these isomers was found to be [α]^31.5_D ±117.8° in ethanol for isomers of hydrochloride and [α]¹³_D ±127.4° in chloroform for those of hydrobromide. Moreover, it was recognized that the racemic modifications of these salts were racemic mixtures and not racemic compounds, by the investigation of the melting point-composition diagrams and infrared absorption spectra.

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Studies on Thiophene Derivatives. III. Clinical Application of 3-Piperidino-1, 1-di (2-thienyl)-1-butene as a New Antitussive.

Ryuichi Kimura, Masanao Ogawa, Takahiro Yabuuchi

1959 Volume 7 Issue 2 Pages 175-176
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.175

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Studies on the Periodic Acid Oxidation of N-Glycosides. XIII. Studies on the Periodic Acid Oxidation of Anilines. (6).

Hiroya Tanabe

1959 Volume 7 Issue 2 Pages 177-183
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.177

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The mechanisms of formation of products obtained by oxidation of aniline with periodic acid, (I) to (VI) reported in Part X of this series, are discussed. Mechanism for the production of (I), (IV), and (VI) is considered to involve the action of hydroxyl radical. In the formation of (V) from N-phenyl-p-benzoquinone diimine, a radical reaction is assumed to play a part.

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Studies on the Synthesis of Amino Acids by the Schmidt Reaction. III. Synthesis of DL-Homolysine.

Seishi Takagi, Kyozo Hayashi

1959 Volume 7 Issue 2 Pages 183-186
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.183

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Harris, et al. synthesized DL-homolysine (IV) by the acetamidomalonate method and obtained its monohydrochloride monohydrate as crystals melting at 176°. (IV) was prepared as its monohydrochloride, m.p. 263°, by the reaction of hydrazoic acid and 1, 1, 6-hexanetricarboxylic acid, which was obtained from cyclohexanone, and (IV) was derived to its benzoate. Two different methods of preparation were further tried, one from 7-aminoheptanoic acid and the other from 1-chloro-5-benzamidopentane, and the same substance melting at 263° was obtained in both cases. The procedure reported by Harris, et al. was followed exactly but the substance of m.p. 263° was obtained instead of that melting at 176° reported by Harris, et al.

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Studies on the Synthesis of Amino Acids by the Schmidt Reaction. IV. Synthesis of DL-Homoserine.

Kyozo Hayashi

1959 Volume 7 Issue 2 Pages 187-191
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.187

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DL-Homoserine is an amino acid which is important in the biochemical study on the metabolism of amino acids. Several methods for the synthesis of DL-homoserine have been reported, but they have many disadvantages ; for example, they involve long process of reaction and extremely complicated method of separation of DL-homoserine formed. By the Schmidt reaction, DL-2-amino-4-alkoxybutyric acid and ethyl 2-acetamido-4-alkoxybutyrate were obtained respectively from (2-alkoxyethyl) malonic acid and 2-(2-alkoxyethyl) acetoacetate, and they were hydrolyzed with 48% hydrobromic acid to DL-2-amino-γ-butyrolactone hydrobromide. This was deacidified with ion exchange resin and simultaneously the ring cleavage was effected, giving DL-homoserine in a good yield and without difficulties in isolation and purification.

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Uber eine neue Nitrierung des Chinolin-N-oxydes. (2).

Eiji Ochiai, Chikara kaneko

1959 Volume 7 Issue 2 Pages 191-195
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.191

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Bei der Nitrierung von Chinolin-N-oxyd mit uberschussigem Benzoylnitrat in Chloroform-Losung entsteht ausser 3-Nitrochinolin-N-oxyd eine nadelformige schwachgelbe Substanz vom Schmp. 258° (u. Zers.) als das Hauptprodukt, dessen Konstitution als N-Benzoyloxy-3, 6-dinitrocarbostyril festgestellt wurde. Das letztere entsteht auch bei analoger Nitrierung von 3- bzw. 6-Nitrochinolin-N-oxyd mit Benzoylnitrat. 5-bzw. 7-Nitrochinolin-N-oxyd ergab bei ganz analoger Nitrierung mit Benzoylnitrat je ein isomeres Produkt von der Zusammensetzung C₁₆H₉O₇N₃, dessen Konstitution hochstwahrscheinlich 3, 5- bzw. 3, 7-Dinitro-N-benzoyloxycarbostyril ist.

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Nitrierung des 6-Methyl-und 3-Bromchinolin-N-oxydes mit Benzoylnitrat.

Eiji Ochiai, Chikara Kaneko

1959 Volume 7 Issue 2 Pages 195-198
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.195

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Die Nitrierung des 6-Methyl- bzw. 3-Bromchinolin-N-oxydes mit Benzoylnitrat verlauft prinzipiell ganz ahnlich wie beim Chinolin-N-oxyd. Es entsteht ein Mononitroderivat des entsprechenden Chinolin-N-oxydes und N-Benzoyloxycarbostyrils. Zu bemerken ist dabei, dass wegen der Blockierung der 3-bzw. 6-Stellung nur die Mononitrierung auf 6- bzw. 3-Stellung und keine weitere Nitrierung stattfindet.

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cis, cis-und trans, trans-1-Methyl-4-hydroxy-3, 5-bis (athoxycarbonylmethyl) piperidin.

Kyosuke Tsuda, Kiyoshi Sakai

1959 Volume 7 Issue 2 Pages 199-205
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.199

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1-Methyl-3, 5-bis (athoxycarbonylmethyl)-piperidon- (4) (IV), welches durch Mannich-Reaktion hergestellt wird, liefert bei der katalytischen Reduktion die zwei stereoisomeren 4-Hydroxy-Verbindungen (Va und Vb). Es wird demnach gezeigt, dass die Struktur von (IV) als Meso-Form bezeichnet werden kann. Durch Tauschen des N-Methyl-Rests von (Va) bzw. (Vb) mit Benzoyl-Rest entsteht (VIIIa) bzw. (VIIIb). (VIIIa) kann mit 10-proz. HCl oder Ac₂O zum γ-Lacton ubergefuhrt werden. Dagegen wird aus (VIIIb) mit 10-proz. HCl nur die Hydroxy-dicarbonsaure erhalten. Die Struktur von (Va) bzw. (Vb) kann somit der cis, cis-Form bzw. trans, trans-Form zugeordnet werden. Bei der NaBH₄-Reduktion von (IV) entstenden nur die 4-Hydroxy-Verbindungen der trans, trans-Reihe. Ausserdem kann (Vb) mit SOCl₂ leicht zur 4-Chlor-Verbindung verwandelt werden. Es ist damit anzunehmen, dass (Va) bzw. (Vb) die Konstellation von 3e : 4a : 5e (XXa) bzw. 3e : 4e : 5e (XXb) besitzt.

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Studies on the Syntheses of Polymethylenebisthioureas and their Derivatives. I.

Seishi Takagi, Hisashi Tanaka, Minoru Yano, Katsunosuke Machida

1959 Volume 7 Issue 2 Pages 206-208
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.206

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Polymethylenebisthioureas were synthesized from diamines by two methods. In one method, diamines were converted into corresponding bisisothiocyante and then treated with ammonia. In the other method, benzoyl isothiocyanate was reacted with diamines and N-benzoyl derivatives obtained were decomposed to form bisthioureas. Better yield was achieved by the latter method. Polymethylenebisthiosemicarbazides and polymethylene-bis-thioureas were also synthesized. These compounds were submitted to pharmacological test as a possible ganglion blocker.

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Synthese von Derivaten der Cinchona-Alkaloide. XXIX. Uber Dihydroepinichin und seine Acylwanderung.

Yoshiro Kobayashi

1959 Volume 7 Issue 2 Pages 209-212
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.209

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N-Benzoyldihydronichin (I) geht beim Behandeln mit Thionylchlorid in das epimere N-Benzoyldihydroepinichin (II) uber. (II) ergab beim Erhitzen mit Salzsaure das Dichlorhydrat des O-Benzoyldihydroepinichins (III), welches beim Befreien der Base mit Ammoniak wieder in (II) zuruckgeht. Diese Eigenschaften stimmen mit der mesoiden bzw. racemoiden Konfiguration bei 8 und 9 Kohlenstoffatomen des Dihydronichins bzw. Dihydroepinichins uberein.

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Studies on the Constitutents of Digitalis purpurea L. X. Isolation of Several New Glycosides from the Water-soluble Fraction of Digitalis Seeds.

Atsuji Okano, Kazuhiko Hoji, Tosaku Miki, Akio Sakashita

1959 Volume 7 Issue 2 Pages 212-221
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.212

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Several new glycosides were isolated from digitalis seeds. Five substances, A-VI acetate, C-I', A-VII, B-II, and X₁, were obtained as crystals, and four substances, B-III, C-II, A-VII', and B-III', were obtained as a colorless powder. In accordance with their colorations and absorption spectra, it was assumed that A-VI, A-VII', B-III, and B-III' belong to gitoxigenin series, C-I' and C-II to digitoxigenin series, and B-II to digitanol series.

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Studies on the Constituents of Digitalis purpurea L. XI. Digifucocellobioside, a New Cardiotonic Glycoside from Digitalis Seeds.

Atsuji Okano, Kazuhiko Hoji, Tosaku Miki, Akio Sakashita

1959 Volume 7 Issue 2 Pages 222-225
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.222

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The structure of substance C-II, newly isolated by the writers and described in the preceding paper, was examined. This substance occurs as a crystalline powder, m.p. 238∼242°(Kofler, uncorr.), C₄₁H₆₄O₁₈·2H₂O ; [α]²⁰_D-1.4° ; U.V. λ^EtOH_max 218 mμ (log ε 4.22). The sugar portion obtained by hydrolysis of Kiliani method was identified as fucose and glucose on paper chromatography. The partial decomposition of substance C-II afforded glucodigifucoside (digitoxigenin β-D-glucosido-β-D-fucoside), by elimination of one mole of glucose. The acetolysis of the acetate of substance C-II gave α-octaacetylcellobiose and it was established that substance C-II is digitoxigenin β-cellobiosido-β-D-fucoside. This is a new cardioglycoside and was named digifucocellobioside.

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Studies on the Constituents of Digitalis purpurea L. XII. New Cardiotonic Glycosides, Gitorocellobioside, Glucogitoroside, and Gitoxin-cellobioside.

Atsuji Okano, Kazuhiko Hoji, Tosaku Miki, Akio Sakashita

1959 Volume 7 Issue 2 Pages 226-232
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.226

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The structures of substance B-III and B-III', newly isolated from digitalis seeds, were examined. It was found that enzymatic hydrolysis of substance B-III afforded gitoroside, and a mild acid hydrolysis afforded gitoxigenin and new trisaccharide which consists of cellobiose and digitoxose. This sugar was named digilanidotriose. Therefore, substance B-III is formulated as gitoxigenin cellobiosido-digitoxoside, and was designated as gitorocellobioside. The partial decomposition of gitorocellobioside with a snail enzyme afforded a new diglycoside which is gitoxigenin glucosido-digitoxoside and this was designated as glucogitoroside. Substance B-III' was examined by the same method and was shown to be a new cardiotonic pentaglycoside which has a structure of gitoxigenin cellobiosido-tridigitoxoside, and was named gitoxin cellobioside.

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Steroid Studies. XI. On the Methylation of 3-Oxosteroids. (1).

Kyosuke Tsuda, Shigeo Nozoe

1959 Volume 7 Issue 2 Pages 232-238
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.232

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By consecutive formylation, methylation, and deformylation, 4, 22-stigmastadien-3-one (IV) affords 2α-methyl-4, 22-stigmastadien-3-one (VII), while the same treatment of the 5α-dihydro compound (VIII) of (IV) gives the 2α-methyl derivative (XI), which agrees with the reduction product of (VII) with lithium in liquid ammonia. The same treatment of the 5β-dihydro compound (XIIIa) of (IV) forms the 4β-methyl derivative (XXa). These experimental results are consistent with the general rule that the 2-position in 3-oxo-5α-steroids and 4-position of 3-oxo-5β-steroids are active.

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Steroid Studies. XII. On the Methylation of 3-Oxosteroids. (2).

Kyosuke Tsuda, Shigeo Nozoe

1959 Volume 7 Issue 2 Pages 238-240
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.238

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Formylation of progesterone (I) gives the 2, 21-bis (hydroxymethylene) compound (II) and 2-hydroxymethylene compound (III). Methylation of (III) and subsequent deformylation affords 2α-methylprogesterone (V). Formylation of the 5α-dihydro compound (VIII) of (I) results in the sole formation of the 2-hydroxymethylene compound (IX), and its methylation followed by deformylation gives the 2α-methyl derivative (VI). On the contrary, the 5β-dihydro compound (X) of (I) affords only the 4, 21-bis (hydroxymethylene) compound (XI).

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Syntheses of Allied Compounds of Lupine Alkaloids. III. Synthesis of 3, 6-Dioxo-1H, 3H, 6H-pyrano [3, 4, 5-i, j] quinolizine.

Yoshinobu Sato

1959 Volume 7 Issue 2 Pages 241-247
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.241

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2-Cyanomethyl-3-methoxymethylpyridine and ethyl (3-methoxymethyl-2-pyridyl) acetate were prepared from ethyl 2-methylnicotinate. Condensation of these compounds with diethyl ethoxymethylenemalonate afforded 1, 3-bis (ethoxycarbonyl)-9-methoxymethyl-4-oxo-4H-quinolizine and 1-cyano-3-ethoxycarbonyl-9-methoxymethyl-4-oxo-4H-quinolizine. The ethoxycarbonyl group in these compounds was saponified and further decarboxylated on being heated with hydrochloric acid. A more drastic condition easily afforded 3, 6-dioxo-1H, 3H, 6H-pyrano [3, 4, 5-i, j] quinolizine.

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Syntheses of Allied Compounds of Lupine Alkaloids. IV. Synthesis and Hydrogenation of 4-Oxo-4H-quinolizine Derivatives.

Yoshinobu Sato

1959 Volume 7 Issue 2 Pages 247-251
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.247

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Three-step reduction of 3, 6-dioxo-1H, 3H, 6H-pyrano [3, 4, 5-i, j] quinolizine (I) and a compound derived from it, 3, 6-dioxo-2-methyl-2, 3-dihydro-1H, 6H-pyrido [3, 4, 5-i, j] quinolizine (III), respectively afforded perhydropyrano [3, 4, 5-i, j] quinolizine (XVI) and 2-methylperhydropyrido [3, 4, 5-i, j] quinolizine (XIX). It was concluded that both compounds possess the cis-quinolizidine ring.

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Studies on the Syntheses of Polymethylene-bisthioureas and their Derivatives. II. Syntheses of Polymethylenediamino-2, 2'-bis (4-methylthiazolium) and S, S'-Dialkyl-polymethylene-bisthiuronium Salts.

Hisashi Tanaka, Minoru Yano, Katsunosuke Machida

1959 Volume 7 Issue 2 Pages 252-253
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.252

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Carotenoids of Staphylococcus citreus.

Tatsuo Ohta, Toshio Miyazaki, Teruo Ninomiya

1959 Volume 7 Issue 2 Pages 254-255
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.254

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The presence of sarcinene and sarcinaxanthin was postulated in a Staphylococcus citreus strain.

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Ableitung des 10-Methoxydihydrocorynantheans aus Chinin.

Eiji Ochiai, Masayuki Ishikawa

1959 Volume 7 Issue 2 Pages 256-258
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.256

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Further Studies on the Absolute Configuration of Naramycin-A (Cycloheximide) and its Isomeric Naramycin-B

Tomoharu Okuda

1959 Volume 7 Issue 2 Pages 259-262
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.259

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Reaction of 1-(Phenethyl)-2 (1H)-pyridones with Phosphoryl Chloride. Formation of 1-(Phenethyl)-2-chloropyridinium Salts.

Shigehiko Sugasawa, Sanya Akaboshi, Yoshio Ban

1959 Volume 7 Issue 2 Pages 263-264
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.263

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Structure of Gitorin

Yoshio Sasakawa

1959 Volume 7 Issue 2 Pages 265
Published: March 20, 1959
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.7.265

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