[3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with diazo compounds and nitrilimines – synthesis of pyrazolines and pyrazoles View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2021-11

AUTHORS

Yuriy N. Маrkitanov, Vadim М. Тimoshenko, Sergiy S. Мykhaylychenko, Eduard B. Rusanov, Alexandr I. Khyzhan, Yuriy G. Shermolovich

ABSTRACT

1,3-Dipolar cycloaddition reactions of 3,3,3-trifluoropropene derivatives containing a sulfonyl, sulfamide, or sulfoximine substituent in position 1 with diazomethane proceed with the formation of 3-substituted 4-(trifluoromethyl)-4,5-dihydro-1H-pyrazoles and 3-(trifluoromethyl)-1H-pyrazole, whereas reactions with ethyl diazoacetate and 2,2,2-trifluorodiazoethane lead to the formation of isomeric 5(3)-substituted 4-trifluoromethyl-3,4(4,5)-dihydro-2(1)H-pyrazoles and 4-substituted 5-(trifluoromethyl)-4,5-dihydro-1Hpyrazoles, the stability of which depends on the nature of the heteroatomic substituent. The cycloaddition of 1-sulfonyl- and 1-sulfamoylsubstituted derivatives of 3,3,3-trifluoropropene to C-carbethoxy-N-phenylnitrilimine gives rise to 4-substituted ethyl 1-phenyl-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxylates and ethyl 1-phenyl-4-(trifluoromethyl)-1H-pyrazole-3-carboxylate. More... »

PAGES

1107-1115

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s10593-021-03029-8

DOI

http://dx.doi.org/10.1007/s10593-021-03029-8

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1144440253


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