A convenient synthesis of ortho-ortho disubstituted biphenyls containing an eight-membered lactam ring using radical chemistry

C. H. Wang; S. Alluri; A. K. Ganguly

doi:10.1016/j.tetlet.2009.02.031

A convenient synthesis of ortho-ortho disubstituted biphenyls containing an eight-membered lactam ring using radical chemistry

C. H. Wang
, S. Alluri
, A. K. Ganguly

Department of Chemistry and Chemical Biology

Stevens Institute of Technology

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

Compound 4 prepared from Isatin in two steps underwent an unusual radical-induced rearrangement reaction to yield 9 as the major product and 10 as the minor component. Compound 9 shows structural similarities to the antimitotic agent rhazinilam and the gamma secretase inhibitor LY411575. The scope of the reaction has been studied by changing the substitutions on the aromatic rings and the mechanism for the formation of 9 and 10 from 4 is suggested.

Original language	English
Pages (from-to)	1879-1881
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2009.02.031
State	Published - 29 Apr 2009

Keywords

Ortho-ortho disubstituted biphenyls
Radical reaction

Access to Document

10.1016/j.tetlet.2009.02.031

Cite this

@article{d1a37c2d347d4f55ad9176537db87d4e,

title = "A convenient synthesis of ortho-ortho disubstituted biphenyls containing an eight-membered lactam ring using radical chemistry",

abstract = "Compound 4 prepared from Isatin in two steps underwent an unusual radical-induced rearrangement reaction to yield 9 as the major product and 10 as the minor component. Compound 9 shows structural similarities to the antimitotic agent rhazinilam and the gamma secretase inhibitor LY411575. The scope of the reaction has been studied by changing the substitutions on the aromatic rings and the mechanism for the formation of 9 and 10 from 4 is suggested.",

keywords = "Ortho-ortho disubstituted biphenyls, Radical reaction",

author = "Wang, \{C. H.\} and S. Alluri and Ganguly, \{A. K.\}",

year = "2009",

month = apr,

day = "29",

doi = "10.1016/j.tetlet.2009.02.031",

language = "English",

volume = "50",

pages = "1879--1881",

number = "17",

}

TY - JOUR

T1 - A convenient synthesis of ortho-ortho disubstituted biphenyls containing an eight-membered lactam ring using radical chemistry

AU - Wang, C. H.

AU - Alluri, S.

AU - Ganguly, A. K.

PY - 2009/4/29

Y1 - 2009/4/29

N2 - Compound 4 prepared from Isatin in two steps underwent an unusual radical-induced rearrangement reaction to yield 9 as the major product and 10 as the minor component. Compound 9 shows structural similarities to the antimitotic agent rhazinilam and the gamma secretase inhibitor LY411575. The scope of the reaction has been studied by changing the substitutions on the aromatic rings and the mechanism for the formation of 9 and 10 from 4 is suggested.

AB - Compound 4 prepared from Isatin in two steps underwent an unusual radical-induced rearrangement reaction to yield 9 as the major product and 10 as the minor component. Compound 9 shows structural similarities to the antimitotic agent rhazinilam and the gamma secretase inhibitor LY411575. The scope of the reaction has been studied by changing the substitutions on the aromatic rings and the mechanism for the formation of 9 and 10 from 4 is suggested.

KW - Ortho-ortho disubstituted biphenyls

KW - Radical reaction

UR - https://www.scopus.com/pages/publications/61749103011

UR - https://www.scopus.com/pages/publications/61749103011#tab=citedBy

U2 - 10.1016/j.tetlet.2009.02.031

DO - 10.1016/j.tetlet.2009.02.031

M3 - Article

AN - SCOPUS:61749103011

SN - 0040-4039

VL - 50

SP - 1879

EP - 1881

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

A convenient synthesis of ortho-ortho disubstituted biphenyls containing an eight-membered lactam ring using radical chemistry

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this