Synthesis of B,O,N-Doped Adamantanes and Diamantanes by Condensation of Oximes with Boronic Acids

Synthesis of B,O,N-Doped Adamantanes and Diamantanes by Condensation of Oximes with Boronic Acids Full article

Journal

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

Output data

Year: 2015, Volume: 80, Number: 13, Pages: 6728-6736 Pages count : 9 DOI: 10.1021/acs.joc.5b00892

Authors

Golovanov Ivan S. ¹ , Sukhorukov Alexey Yu. ¹ , Nelyubina Yulia V. ² , Khomutova Yulia A. ¹ , Ioffe Sema L. ¹ , Tartakovsky Vladimir A. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991, Moscow, Russia
2	A.N. Nesmeyanov Institute of Organoelement Compounds, Vavilov str. 28, 119991, Moscow, Russia

Condensation of oximes with boronic acids RB(OH)2 or B(OH)3 affords remarkably stable 2,4,10-trioxa-1,5,7-triaza-3-boroadamantanes via an unprecedented multicomponent process. The mechanism involves the reversible generation of unstable oxime cyclotrimers, which are readily intercepted by boronic acids.

Golovanov I.S. , Sukhorukov A.Y. , Nelyubina Y.V. , Khomutova Y.A. , Ioffe S.L. , Tartakovsky V.A.
Synthesis of B,O,N-Doped Adamantanes and Diamantanes by Condensation of Oximes with Boronic Acids
Journal of Organic Chemistry. 2015. V.80. N13. P.6728-6736. DOI: 10.1021/acs.joc.5b00892 WOS Scopus OpenAlex

Web of science:	WOS:000357624100023
Scopus:	2-s2.0-84942465445
OpenAlex:	W2409476181

DB	Citing
OpenAlex	22
Scopus	21
Web of science	20