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Rearrangement of ketone hydrazones derived from 4‐hydrazino‐1 H ‐2,3‐benzoxazines
Author(s) -
Pifferi Giorgio,
Vigevani Aristide,
Consonni Pietro,
Gallo Gian Gualberto
Publication year - 1972
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.5570090411
Subject(s) - chemistry , ketone , anhydrous , hydrolysis , methyl ketone , medicinal chemistry , organic chemistry , computational chemistry
The ketone hydrazones IV, derived from 4‐(1‐methylhydrazino)‐1 H ‐2,3‐benzoxazines and various ketones, rearrange by the action of anhydrous acids and/or heating to the phthalanylidene compounds V, which are the first reported examples of α‐aminoazoaliphatic derivatives. The structure assignment was based on spectroscopic (ir, pmr, and uv) data and on the study of the hydrolysis products. A mechanism for the rearrangement is proposed and briefly discussed.