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Thiophene systems. 6 . An unexpected bromine migration during the synthesis of thieno[3,4‐ b ][1,5]benzoxazepin‐10‐ones
Author(s) -
Press Jeffery B.,
Eudy Nancy H.
Publication year - 1981
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.5570180641
Subject(s) - chemistry , bromine , thiophene , ring (chemistry) , closure (psychology) , chlorine , alkoxy group , medicinal chemistry , stereochemistry , organic chemistry , alkyl , economics , market economy
7‐Bromothieno[3,4‐ b ][1,5]benzoxazepin‐10‐one ( 1a ) was unexpectedly formed upon acid catalyzed ring closure of 5‐bromo‐4‐ethoxy‐2′‐hydroxy‐3‐thiophenecarboxanilide ( 2a ). Ring closure of the chlorine analogue 2c proceeded normally to give 3‐chlorothieno[3,4‐ b ][1,5]benzoxazepin‐10‐one ( 1b ).