Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Heterocyclic Enaminonitriles. V. Reactions of 2-Amino-3-cyano-1-ethoxycarbonyl-4, 5-dihydropyrroles with Acetylenic Esters
HISASHI MATSUNAGAMIKI SONODAYUKIHIKO TOMIOKAMOTOYOSHI YAMAZAKI
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Keywords: ring contraction
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1984 Volume 32 Issue 7 Pages 2596-2601

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Abstract
The reactions of 2-amino-3-cyano-1-ethoxycarbonyl-4, 5-dihydropyrrole (Ia) and 2-amino-3-cyano-1-ethoxycarbonyl-5-methyl (or 4-phenyl)-4, 5-dihydropyrrole (Ib or Ic) with dimethyl acetylenedicarboxylate and methyl propiolate gave the corresponding 7-amino-4-cyano-1-ethoxycarbonyl-2, 3-dihydro-1H-azepines (IIa-c and IIIa-c). On heating with 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone, IIc and IIIc were converted into dimethyl 6-amino-3-cyano-5-ethoxycarbonylamino-4-phenyl-1, 2-benzenedicarboxylate (V) and methyl 6-amino-3-cyano-5-ethoxycarbonylamino-4-phenylbenzenecarboxylate (VI), respectively.
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© The Pharmaceutical Society of Japan
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