Reactions of donor-acceptor cyclopropanes or benzylidenemalonate with benzyl azide by generating gallium trichloride 1,2-zwitterionic complexes
- Авторлар: Borisova I.1, Tarasova A.1, Potapov K.1, Novikov R.1, Tomilov Y.1
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Мекемелер:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- Шығарылым: Том 68, № 8 (2019)
- Беттер: 1504-1509
- Бөлім: Full Article
- URL: https://journals.rcsi.science/1066-5285/article/view/243445
- DOI: https://doi.org/10.1007/s11172-019-2584-2
- ID: 243445
Дәйексөз келтіру
Аннотация
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.
Авторлар туралы
I. Borisova
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: tom@ioc.ac.ru
Ресей, 47 Leninsky prosp., Moscow, 119991
A. Tarasova
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: tom@ioc.ac.ru
Ресей, 47 Leninsky prosp., Moscow, 119991
K. Potapov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: tom@ioc.ac.ru
Ресей, 47 Leninsky prosp., Moscow, 119991
R. Novikov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: tom@ioc.ac.ru
Ресей, 47 Leninsky prosp., Moscow, 119991
Yu. Tomilov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Хат алмасуға жауапты Автор.
Email: tom@ioc.ac.ru
Ресей, 47 Leninsky prosp., Moscow, 119991