Synthesis of Functional Derivatives of Benzodifurazan {Benzo[1,2- c :3,4- c ’]bis([1,2,5]oxadiazole)}

Vladimir A. Samsonov; Самсонов Владимир Анатольевич; Yuri V. Gatilov; Гатилов Юрий Васильевич; Arkady O. Bryzgalov; Брызгалов Аркадий Олегович

doi:10.31857/S0514749225040154

Synthesis of Functional Derivatives of Benzodifurazan {Benzo[1,2-c:3,4-c’]bis([1,2,5]oxadiazole)}

Authors: Samsonov V.A.¹, Gatilov Y.V.¹, Bryzgalov A.O.¹
Affiliations:
1. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the RAS
Issue: Vol 61, No 4 (2025)
Pages: 484-494
Section: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
URL: https://rjpbr.com/0514-7492/article/view/689700
DOI: https://doi.org/10.31857/S0514749225040154
EDN: https://elibrary.ru/SEUEJG
ID: 689700

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Abstract

We have found that BDP reacts with 1,3-dibromo-5,5-dimethylhydantoin in sulfuric acid to form 5-bromo-4,5-dihydrobenzo[1,2-c:3,4-c']bis([1, 2,5]oxadiazol)-4-ol, which upon treatment with a base (calcium hydroxide) turns into 1a,7b-dihydrooxireno[2',3':5,6]benzo[1,2-c:3,4-c ']bis([1,2,5]oxadiazole). The structure of the compound was established by X-ray diffraction. The resulting compound exhibits the usual properties of epoxides. Easily adds nucleophiles to form the corresponding alcohols, which, when treated with p-toluenesulfonyl chloride in the presence of tetrabutylammonium bromide and sodium hydroxide in benzene, give functional derivatives of BDF.

Keywords

benzodifurazan, oxiranes (epoxides), phase transfer catalysis, 1,3-dibromo-5,5-dimethylhydantoin

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