18076-03-4Relevant articles and documents
Cascade reaction to 1H-pyrazoles from hydrazones via sodium Ni-trite promoted dual C–C/C–N formation, annulation and aromatization with 1,2-dichloroethane
Hao, Liqiang,Liu, Hongyan,Zhang, Zheng,Wen, Fuqiang,Xia, Chengcai,Pang, Zengfen
, p. 2309 - 2312 (2021/03/16)
A novel route for tandem C–C/C–N formation, annulation and aromatization of hydrazones with 1,2-dichloroethane to synthesize 1H-pyrazoles has been developed. Furthermore, the 1,2-dichloroethane serves as alkylation reagent in good to excellent yields. This methodology features mild reaction conditions and good functional group tolerance, providing a direct approach for the preparation of 1H-pyrazoles.
Synthesis of 1-Aza-6,7-dehydrotropanes via Copper(I)-Catalyzed Coupling of 5-Chloropentan-2-one with Hydrazines and Terminal Alkynes
Van Beek, Wim E.,Weemaes, Karel,Herrebout, Wouter A.,Vande Velde, Christophe M. L.,Tehrani, Kourosch Abbaspour
supporting information, p. 2643 - 2647 (2018/12/13)
A one-pot, three-component, Cu(I)-catalyzed coupling of primary hydrazines, 5-chloropentan-2-one, and terminal alkynes was developed. The resulting 1-aza-6,7-dehydrotropanes compose a new class of substances while related 1-azatropanes are scarcely described in literature and closely resemble tropane alkaloids. Hydrogenation of the double bond in 1-aza-6,7-dehydrotropanes triggered a rearrangement, involving a [1,3]-hydride shift, forming cyclic hydrazones.
Thermolyses of 1,1-dimethyl-2-pyrazolinium fluoborates - Evidence for spiro--1-aza-1,4,6-octatrienyl cation
Subramaniam, Girija,Fishel, Derry L
, p. 172 - 176 (2007/10/02)
Thermolyses of 3-aryl-1,1-dimethyl-2-pyrazolinium fluoborates give an isomeric mixture of 3-aryl-1-methylpyrazole and 5-aryl-1-methylpyrazole as major products in complete contrast to the corresponding acyclic analogs. 2,6-Diaryl-3-methylpyridines were isolated only in trace quantities.The probable reasons for this unique behaviour was explored using semi-empirical calculations, non-kinetic methods and radiolabelling experiments.A pathway was proposed.
The Reaction of 1,1-Dimethyl-1-Phenacylhydrazinium Bromide with Aqueous Sodium Hydroxide
Kano, Kunio,Anselme, Jean-Pierre
, p. 905 - 907 (2007/10/02)
The reaction of 1,1-dimethyl-1-phenacylhydrazinium bromide with 1 M aqueous sodium hydroxide give benzoic acid, 3-phenyl-1-methylpyrazole, 5-benzoyl-3-phenyl-1-methylpyrazole, and benzonitrile as the major components; the expected product, 2-benzoyl-5-phenylimidazole was formed in only small amounts.Mechanisms to rationalize the formation of the major products are discussed.