Synthesis and some properties of 2H-benzimidazole 1,3-dioxides

Synthesis and some properties of 2H-benzimidazole 1,3-dioxides Full article

Journal

Tetrahedron
ISSN: 0040-4020

Output data

Year: 2015, Volume: 71, Number: 39, Pages: 7233-7244 Pages count : 12 DOI: 10.1016/j.tet.2015.03.096

Tags

Benzofuroxan; 2H-benzimidazole 1,3-dioxide; 3H-[2,1,4]benzoxadiazine 4-oxide; Thermal transformations; Photochromic compounds

Authors

Chugunova Elena ¹ , Samsonov Vladimir ² , Gerasimova Tatiana ² , Rybalova Tatiana ^2,3 , Bagryanskaya Irina ^2,3

Affiliations

1	A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov St., 420088, Kazan, Russia
2	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Prosp, Akad. Lavrentґeva, 630090, Novosibirsk, Russia
3	Novosibirsk State University, Pirogova Str. 2, 630090, Novosibirsk, Russia

The synthesis of novel 2H-benzimidazole 1,3-dioxides on the basis of benzofuroxans interaction with alcohols in acids is described. The formation of a stable secondary carbocation from alcohol is necessary for formation of 2H-benzimidazole 1,3-dioxide while substituents in benzofuroxans don't prevent the reaction. Under heating 2H-benzimidazole 1,3-dioxides are rearranged to 3H-[2,1,4]benzoxadiazine 4-oxides whose stability depends on substituents in the aromatic ring. Under irradiation oxadiazines are converted back to 2H-benzimidazole 1,3-dioxides. (C) 2015 Elsevier Ltd. All rights reserved.

Chugunova E. , Samsonov V. , Gerasimova T. , Rybalova T. , Bagryanskaya I.
Synthesis and some properties of 2H-benzimidazole 1,3-dioxides
Tetrahedron. 2015. V.71. N39. P.7233-7244. DOI: 10.1016/j.tet.2015.03.096 WOS Scopus РИНЦ

Published print:

Sep 1, 2015

Web of science	WOS:000360511000018
Scopus	2-s2.0-84939258700
Elibrary	24509227
OpenAlex	W2327005696