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Preparation of pyrazolo[5,1‐ c ][1,4]benzoxazines by intramolecular [3 + + 2] cycloaddition reaction of hydrazonium chlorides with alkenes
Author(s) -
Shimizu Tomio,
Hayashi Yoshiyuki,
Miki Masayuki,
Teramura Kazuhiro
Publication year - 1990
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.5570270629
Subject(s) - chemistry , cycloaddition , intramolecular force , phenylhydrazine , hydrochloric acid , cationic polymerization , medicinal chemistry , intramolecular reaction , 1,3 dipolar cycloaddition , organic chemistry , catalysis
Pyrazolo[5,1‐ c ][1,4]benzoxazines were prepared by the reaction of 2‐(allyloxy)phenylhydrazine with arylaldehydes in the presence of hydrochloric acid. The formation of the fused heterocycles can be explained by intramolecular 1,3‐dipolar cycloaddition reaction of cationic dipole, i.e ‥, hydrazonium chlorides.