Transformations of tetrahydro-1,4-benzoxazepines and tetrahydro-1,4- benzothiazepines under the action of alkynes. First example of the synthesis of tetrahydro-1,4-benzothiazonine-6-carboxylate

It was shown that 2,3,4,5-tetrahydro-1,4-benzoxazepines were cleaved at the N-C(5) bond under the action of activated alkynes in methanol, forming o-(methoxyethyl)- and o-(methoxybenzyl)-phenyl(aminoethyl) ethers. The cleavage rate depended on the electronic effects of the substituents at the C-5 atom. Thiazepine ring expansion in tetrahydro-1,4-benzothiazepine was achieved for the first time via reaction with methyl propiolate to give a benzothiazonine. © 2013 Springer Science+Business Media New York.

Publisher
Латвийский институт органического синтеза Латвийской академии наук / Springer New York Consultants Bureau
Number of issue
2
Language
English
Pages
331-340
Status
Published
Volume
49
Year
2013
Organizations
  • 1 Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
Keywords
alkynes; benzothiazepine; benzothiazonine; benzoxazepine; domino reaction; ring cleavage; ring expansion
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/2073/
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