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4‐Substituted‐4 H ‐pyrrolo[2,1‐ c ] [1,4]benzoxazines
Author(s) -
Jirkovsky I.,
Humber L. G.,
Baudy R.
Publication year - 1976
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.5570130222
Subject(s) - chemistry , dimethyl acetylenedicarboxylate , adduct , pyrrole , medicinal chemistry , organic chemistry , cycloaddition , catalysis
The condensations of 1‐(2‐hydroxyphenyl) pyrroles with a variety of carbonyl compounds are shown to give new 4‐substituted‐4 H ‐4‐methylpyrrolo[2,1‐ c ][1,4]benzoxazines. Some of the products were further functionalized. The ir, uv, and pmr spectra of the title heterocyclic system are discussed. Reaction of 1‐(2‐hydroxyphenyl) pyrrole with dimethyl acetylenedicarboxylate yielded dimethyl 3‐(2‐hydroxyanilino) phthalale; a mechanistic rationale which accounts for the result involves a rearrangement of the hypothetical Diels‐Alder adduct.