Reactions of donor-acceptor cyclopropanes or benzylidenemalonate with benzyl azide by generating gallium trichloride 1,2-zwitterionic complexes

Reactions of donor-acceptor cyclopropanes or benzylidenemalonate with benzyl azide by generating gallium trichloride 1,2-zwitterionic complexes Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2019, Volume: 68, Number: 8, Pages: 1504-1509 Pages count : 6 DOI: 10.1007/s11172-019-2584-2

Authors

Borisova I.A. ¹ , Tarasova A.V. ¹ , Potapov K.V. ¹ , Novikov R.A. ¹ , Tomilov Yu.V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation

The reactions of 1,2-zwitterionic complexes, generated from 2-arylcyclopropane-1,1-dicarboxylates (ACDC) or benzylidenemalonate and gallium trichloride, with benzyl azide proceeds as a formal [3+2] cycloaddition to form dihydro-1,2,3-triazoles. The latter, when the reaction mixture is treated with 10% aqueous HCl, undergo retrocyclization with elimination of diazomalonate. The reaction of ACDC, benzyl azide, and GaCl3 with simultaneous mixing of the reagents leads to the interception of the 1,3-zwitterion, with this stage being accompanied by both the cyclization to substituted 1,2,3-triazinine and the elimination of a nitrogen molecule to form 3,4-dihydro-2H-1,2-oxazine structure, which after acid hydrolysis gives substituted 3-hydroxypyrrolidin-2-one.

Borisova I.A. , Tarasova A.V. , Potapov K.V. , Novikov R.A. , Tomilov Y.V.
Reactions of donor-acceptor cyclopropanes or benzylidenemalonate with benzyl azide by generating gallium trichloride 1,2-zwitterionic complexes
Russian Chemical Bulletin. 2019. V.68. N8. P.1504-1509. DOI: 10.1007/s11172-019-2584-2 WOS Scopus OpenAlex

≡ Web of science:	WOS:000481762700004
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