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Synthesis of New Pyrrolo Heterocycles (I): Novel Synthesis of Pyrano[2,3‐ c ]pyrrole, Isoindoline, Pyrrolo[3,4‐ b ]pyridine, and Pyrrolo[3,4‐ d ]pyrimidine Derivatives
Author(s) -
ElAblak F. Z.,
AbuElenein N. S.,
Sofan M. A.
Publication year - 2016
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2520
Subject(s) - chemistry , malononitrile , isoindoline , sodium ethoxide , thiourea , cyanoacetamide , isoindole , pyrrole , pyrimidine , pyridine , ethyl cyanoacetate , medicinal chemistry , proton nmr , thiazole , organic chemistry , stereochemistry , catalysis , ethanol
Michael addition of 1,5‐diaryl‐2,3‐dioxopyrrolidine derivatives with α‐cyanocinnamonitriles and ethyl α‐cyanocinnamates afforded 4 H ‐pyrano[2,3‐ c ]pyrrole derivatives in the presence of sodium ethoxide. Under the same reaction condition, the ylidenes of 1,5‐diaryl‐2,3‐dioxopyrrolidine were reacted with malononitrile or ethyl cyanoacetate to give isoindole derivatives; however, pyrrolo[3,4‐ b ]pyridine derivatives were formed when cyanoacetamide was used. Moreover, pyrrolo[3,4‐ d ]pyrimidine derivatives were synthesized by treating 4‐benzylidene‐1,5‐diphenyl‐2,3‐dioxopyrrolidine with urea and/or thiourea under basic conditions. The structures of all the new synthesized compounds were confirmed by elemental analysis, IR and NMR spectra.