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Synthesis and Structural Characterization of Pyrrole Heterocyclic Systems Bearing Amino Acid Units: Novel Pyrrol‐3‐ones, Pyrrolo[1,2‐ a ][3,1]benzoxazines, and Pyrrolo[2,1‐ b ][1,3]oxazoles
Author(s) -
Koca İrfan,
Saçmacı Mustafa,
Yılmaz Filiz,
Üngören Şevket Hakan
Publication year - 2014
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.1509
Subject(s) - chemistry , anthranilic acid , pyrrole , furan , intramolecular force , stereochemistry , medicinal chemistry , organic chemistry
Furan‐3‐one derivatives 1 were converted into 2‐hydroxy‐pyrrole‐3‐ones 4 by reacting with various α‐ and β‐amino acids. In contrast, the reaction of furan‐3‐ones and 1‐aminocyclobutanecarboxylic acid afforded spiro‐pyrrolo[2,1‐ b ][1,3]oxazoles 5 via the pyrrole‐3‐one intermediate under the same reaction conditions. Some of 2‐hydroxy‐pyrrole‐3‐ones 3 derived from anthranilic acids were transformed to pyrrolo[1,2‐ a ][3,1]benzoxazines via intramolecular esterification .