DECARBAMOYLATION OF N-ALKOXY-N-(4-DIMETHYLAMINOPYRIDIN-1-IUM-1-YL)UREAS CHLORIDES IN DIMETHYLSULFOXIDE AS ROUTE TO 1-ALKOXYAMINO-4-DIMETHYLAMINOPYRIDINIUM CHLORIDES | Zendy

Vasiliy G. Shtamburg | Zendy; Victor V. Shtamburg | Zendy; Andrey A. Anishchenko | Zendy; Светлана В. Кравченко | Zendy; Alexander V. Mazepa | Zendy; E.A. Klots | Zendy

Open Access

DECARBAMOYLATION OF N-ALKOXY-N-(4-DIMETHYLAMINOPYRIDIN-1-IUM-1-YL)UREAS CHLORIDES IN DIMETHYLSULFOXIDE AS ROUTE TO 1-ALKOXYAMINO-4-DIMETHYLAMINOPYRIDINIUM CHLORIDES

Author(s) -

Vasiliy G. Shtamburg,

Victor V. Shtamburg,

Andrey A. Anishchenko,

Светлана В. Кравченко,

Alexander V. Mazepa,

E.A. Klots

Publication year - 2018

Publication title -

european chemical bulletin

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.131

H-Index - 5

ISSN - 2063-5346

DOI - 10.17628/ecb.2018.7.267-271

Subject(s) - alkoxy group , chemistry , urea , chloride , substituent , medicinal chemistry , nuclear chemistry , organic chemistry , alkyl

Decarbamoylation of N -alkoxy- N -(4-dimethylaminopyridin-1-ium-1-yl)ureas chlorides in dimethylsulfoxide takes place with forming of 1-alkoxyaminopyridinium chlorides. N -Alkoxy substituent’s nature affects on ease of the decarbamoylation. Decarbamoylation of N - n -butyloxy- N -(4-dimethylaminopyridin-1-ium-1-yl)urea chloride at 20 oC occurs with the selective forming of 1- n -butyloxyamino-4-dimethylaminopyridinium chloride. N -Methoxy- N -(4-dimethylaminopyridin-1-ium-1-yl)urea chloride is stable in dimethylsulfoxide at 20 oC, but it forms selectively 1-methoxyamino-4-dimethylaminopyridium at 82 oC heating during 1 hour. N -Ethoxy- N -(4-dimethylaminopyridin-1-ium-1-yl)urea chloride is also stable in dimethylsulfoxide at 20 oC, but it converts in 1-ethoxyamino-4-dimethylaminopyridinium chloride at 100 oC heating during 3 hour.

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