Synthesis of N,N′-Unsymmetrical 9-Amino-5,7-dimethyl-bispidines | Sciact

Synthesis of N,N′-Unsymmetrical 9-Amino-5,7-dimethyl-bispidines Научная публикация

Журнал

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Вых. Данные

Год: 2023, Том: 88, Номер: 11, Страницы: 7272-7280 Страниц : 9 DOI: 10.1021/acs.joc.3c00514

Авторы

Kalinin Mikhail A. ¹ , Medved’ko Aleksei V. ¹ , Minyaev Mikhail E. ¹ , Vatsadze Sergey Z. ¹

Организации

1	N.D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Russia

A new approach to the preparation of N,N′-unsymmetrically substituted 9-aminobispidines through aminal bridge removal reaction has been developed, the principal feature of which is the ability to selectively functionalize all three nitrogen atoms. The intermediates of 1,3-diazaadamantane’s aminal bridge removal reaction are characterized, and the mechanism of this reaction is proposed based on the analysis of their structures. Representatives of the previously unknown saturated heterocyclic 1,5,9-triazatricyclo[5.3.1.03,8]undecane system were obtained and structurally characterized. Thus, it was possible for the first time to obtain 3,7,9-trisubstituted bispidines containing acetyl, Boc, and benzyl groups at nitrogen atoms, which can be independently removed (orthogonal protective groups).

Kalinin M.A. , Medved’ko A.V. , Minyaev M.E. , Vatsadze S.Z.
Synthesis of N,N′-Unsymmetrical 9-Amino-5,7-dimethyl-bispidines
Journal of Organic Chemistry. 2023. V.88. N11. P.7272-7280. DOI: 10.1021/acs.joc.3c00514 WOS Scopus OpenAlex

Web of science:	WOS:001009697400001
Scopus:	2-s2.0-85162223435
OpenAlex:	W4377565230

БД	Цитирований
OpenAlex	5
Web of science	5
Scopus	5