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Pyrrolidines, Pyrrolines and Pyrroles from 1,4‐Diaryl‐2,3‐dinitro‐1,3‐butadienes via a 5‐ endo‐trig Cyclization
Author(s) -
Dell'Erba Carlo,
Mugnoli Angelo,
Novi Marino,
Pani Marcella,
Petrillo Giovanni,
Tavani Cinzia
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/(sici)1099-0690(200003)2000:6<903::aid-ejoc903>3.0.co;2-p
Subject(s) - chemistry , diastereomer , ring (chemistry) , alkyl , amine gas treating , stereochemistry , nitro , derivative (finance) , medicinal chemistry , crystal structure , pyrrole , organic chemistry , financial economics , economics
Abstract The reactions between 1,4‐diaryl‐2,3‐dinitro‐1,3‐butadienes 1a ‐ d and primary alkylamines gave high yields of N ‐alkyl‐2,5‐diaryl‐3‐alkylamino‐4‐nitropyrrolidines 2 as pure all‐ trans diastereomers via an unusually favoured 5‐ endo ‐ trig ring closure. The stereochemistry of compounds 2 has been attributed through an X‐ray crystal structure analysis of the acetyl derivative 5 of 2ai . Amine elimination from 2 gave the N ‐alkyl‐2,5‐diaryl‐3‐nitro‐3‐pyrrolines 3 which could be easily aromatized to the corresponding pyrroles 4 .