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A Convenient Synthesis of Indole‐Substituted 2‐Pyrrolidones and Their Cyclized Derivatives
Author(s) -
Boisbrun Michel,
Jeannin Laurent,
Toupet Loïc,
Laronze JeanYves
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200009)2000:17<3051::aid-ejoc3051>3.0.co;2-3
Subject(s) - chemistry , indole test , combinatorial chemistry , organic chemistry
Condensation between indole, Meldrum’s acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a−c . The latter were cyclized to indole‐substituted 2‐pyrrolidones 15a−b or 3‐aminopyrrolid‐2‐ones 18a−b , depending on the starting material. Derivative 18a was transformed into pyrrolo[3′,4′:5,6]pyrido[3,4‐ b ]indol‐3(2 H )‐ones 19a and 20a by a Pictet−Spengler condensation with benzaldehyde.