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The Cyclization of Cis‐ and Trans‐ Methoxybenzaldoximes to Methoxy‐3,1,4‐Benzoxadiazepines and Methoxy‐Quinazoline‐3‐Oxides Respectively
Author(s) -
Brown D. J.,
England B. T.
Publication year - 1968
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.196800075
Subject(s) - chemistry , triethyl orthoformate , bicyclic molecule , quinazoline , mass spectrum , cis–trans isomerism , stereochemistry , medicinal chemistry , organic chemistry , ion , catalysis
Cis and trans forms of 2‐amino‐3(4, 5, and 6)‐methoxybenzaldoximes were separated chromatographically and distinguished by their spectra. The trans‐isomers, with triethyl orthoformate, gave 5(6, 7, or 8)‐methoxyquinazoline‐3‐oxide whereas appropriate cis‐isomers gave 7‐ or 9‐methoxy‐3,1,4‐benzoxadiazepine. The structures of the bicyclic products were confirmed by their mass spectra.