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Studies on isocyanides and related compounds. Synthesis of furan derivatives and their transformation into indole derivatives

✍ Scribed by Stefano Marcaccini; Roberto Pepino; Carlos F. Marcos; Cecilia Polo; Tomás Torroba

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
250 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The intramolecular Knoevenagel condensation of N‐cyclohexyl 3‐aryl‐2‐(2‐nitrophenyl)acetoxy‐3‐oxopropionamides 4 obtained from 2‐nitrophenylacetic acid (1), arylglyoxals 2 and cyclohexyl isocyanide (3) afforded N‐cyclohexyl 3‐aryl‐2,5‐dihydro‐2‐(2‐nitrophenyl)‐5‐oxofuran‐2‐carboxamides 6 which underwent reductive cleavage to N‐cyclohexyl (Z)‐3‐aryl‐2‐hydroxy‐3‐(2,3‐dihydro‐2‐oxoindol‐3‐ylidene)propionamides 8 probably via the labile intermediates 7.

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