New simple methods for the preparation of heterocycle-fused quinone derivatives based on tandem Michael addition-cyclization sequence between quinones and enamines (or imines) have been developed. The reaction of 2-hydroxy-1, 4-naphthoquinones with enamines, derived from ketones, afforded 2, 3-disubstituted naphtho [2, 3-
b] furan-4, 9-diones. 1
H-Benz [
f] indole-4, 9-diones could be prepared by treating 2-trifluoroacetylamino-1, 4-naphthoquinone with enamines. The similar pyrrole ring formation took place by using a 2-trifluoroacetylamino-1, 4-benzoquinone to give 1
H-indole-4, 7-diones. 2, 3-Disubstituted naphtho [2, 3-
b] thiophene-4, 9-diones were synthesized from 2- [2- (ethoxycarbonyl) ethylthio] -1, 4-naphthoquinone and enamines. 1
H-Naphtho [2, 3-
c] pyran-5, 10-dione derivatives, including a natural product (pentalongin), were prepared from 2- (1-hydroxyalkyl) -1, 4-naphthoquinones and enamines (or imines). The utility of this method was demonstrated in the synthesis of pyranonaphthoquinone antibiotics, (±) -eleutherin and (±) -isoeleutherin. 1
H-2-Benzopyran-5, 8-dione derivatives were similarly synthesized from 2-alkoxy-6- (1-hydroxyalkyl) -1, 4-benzoquinones. Treatment of 2-acyl-1, 4-naphthoquinones or 2-acyl-5, 6-dimethyl-1, 4-benzoquinones with enamines (or imines), followed by addition of aqueous ammonia, afforded benz [
g] isoquinoline-5, 10-diones or isoquinoline-5, 8-diones, respectively.
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