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Syntheses of α‐Haloformylarylhydrazines and Their Self‐dimerizations
Author(s) -
Kuo C. N.,
Wu M. H.,
Chen S. P.,
Li T. P.,
Huang C. Y.,
Yeh M. Y.
Publication year - 1994
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199400118
Subject(s) - chemistry , aryl , intramolecular force , tetrazine , primary (astronomy) , alkyl , ring (chemistry) , stereochemistry , organic chemistry , combinatorial chemistry , physics , astronomy
α‐Haloformylarylhydrazine hydrohalides 1 were prepared through ring opening of 3‐aryl‐4‐halosydnones 7 with hydrohalic acids in EtOAc in moderate yields. Reactions between compounds 1 and primary alcohols gave alkyl 1‐arylhydrazinecarboxylates 12 and 14, important intermediates in syntheses of antiinflammatory drugs. Compounds 16,4‐aryl‐2‐(arylhydrazin‐1‐y1)‐1,3,4‐oxadiazolin‐5‐ones, and compounds 18, 1,4‐diaryl‐1,4‐dihydro‐1,2,4,5‐tetrazine‐3,6( 2H,5H )‐diones, were synthesized by self‐dimerization of compounds 1. Compounds 18 were also converted to compounds 17 via intramolecular rearrangement. Structural elucidation and verification of the reaction mechanisms are presented.