Premium
The synthesis of methyl 1‐aryl‐2‐pyrrolecarboxylates
Author(s) -
Kiely John S.,
Huang Suchin
Publication year - 1987
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.5570240441
Subject(s) - chemistry , aniline , steric effects , aryl , condensation , alkyl , conjugated system , acetic acid , medicinal chemistry , polar effect , nitrogen , condensation reaction , organic chemistry , catalysis , physics , thermodynamics , polymer
A series of alkyl 1‐(aryl)‐2‐pyrrolecarboxylates were prepared by the condensation of the appropriate aniline with methyl tetrahydro‐2,5‐dimethoxy‐2‐furancarboxylate in refluxing acetic acid. It was found that condensation proceeds even in substituents possessing steric bulk are present in the ortho positions of the aniline. Strong electron withdrawing substituents if conjugated to the nitrogen diverts the reaction from product to unidentified tars.