Benzotriazolyl-mediated 1,2-shifts of electron-rich heterocycles

Alan R. Katritzky*, Sergey Bobrov, Nivine Khachab, Kostyantyn Kirichenko

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The anion formed from the lithiation of 1-[(methylthio)methyl]-1H-benzotriazole 1 with n-BuLi adds to heteroaryl ketones to give 2-benzotriazolyl alcohols 3a-m. Thermolysis of 3a-g in the presence of zinc bromide induces a 1,2-shift of heteroaromatic groups to form ketones 4a-g. By contrast, in the rearrangement of 2-benzotriazolyl alcohols 3h,i,k-m migration of the phenyl group rather than the corresponding heteroaromatic groups occurred to give ketones 4h,i,k-m.

Original languageEnglish (US)
Pages (from-to)4269-4271
Number of pages3
JournalJournal of Organic Chemistry
Volume69
Issue number12
DOIs
StatePublished - Jun 11 2004

ASJC Scopus subject areas

  • Organic Chemistry

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