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

Alan R. Katritzky; Sergey Bobrov; Niveen Khashab; Kostyantyn Kirichenko

doi:10.1021/jo049931+

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

Alan R. Katritzky^*, Sergey Bobrov, Niveen Khashab, Kostyantyn Kirichenko

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	4269-4271
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	69
Issue number	12
DOIs	https://doi.org/10.1021/jo049931+
State	Published - Jun 11 2004
Externally published	Yes

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Organic Chemistry

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@article{cb7bcbd0380c4a4ca5e7cb5c00b379e4,

title = "Benzotriazolyl-mediated 1,2-shifts of electron-rich heterocycles",

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.",

author = "Katritzky, {Alan R.} and Sergey Bobrov and Niveen Khashab and Kostyantyn Kirichenko",

year = "2004",

month = jun,

day = "11",

doi = "10.1021/jo049931+",

language = "English (US)",

volume = "69",

pages = "4269--4271",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "12",

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TY - JOUR

T1 - Benzotriazolyl-mediated 1,2-shifts of electron-rich heterocycles

AU - Katritzky, Alan R.

AU - Bobrov, Sergey

AU - Khashab, Niveen

AU - Kirichenko, Kostyantyn

PY - 2004/6/11

Y1 - 2004/6/11

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=2942562341&partnerID=8YFLogxK

U2 - 10.1021/jo049931+

DO - 10.1021/jo049931+

M3 - Article

C2 - 15176858

AN - SCOPUS:2942562341

SN - 0022-3263

VL - 69

SP - 4269

EP - 4271

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

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

Abstract

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