Reactions of donor-acceptor cyclopropanes or benzylidenemalonate with benzyl azide by generating gallium trichloride 1,2-zwitterionic complexes
- Authors: Borisova I.A.1, Tarasova A.V.1, Potapov K.V.1, Novikov R.A.1, Tomilov Y.V.1
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Affiliations:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- Issue: Vol 68, No 8 (2019)
- Pages: 1504-1509
- Section: Full Article
- URL: https://journals.rcsi.science/1066-5285/article/view/243445
- DOI: https://doi.org/10.1007/s11172-019-2584-2
- ID: 243445
Cite item
Abstract
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.
About the authors
I. A. Borisova
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
A. V. Tarasova
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
K. V. Potapov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
R. A. Novikov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
Yu. V. Tomilov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Author for correspondence.
Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991