Synthesis of highly substituted pyrroles via oxidative free radical reactions of β-aminocinnamates

An I. Tsai; Che Ping Chuang

doi:10.1016/j.tet.2005.12.011

Synthesis of highly substituted pyrroles via oxidative free radical reactions of β-aminocinnamates

An I. Tsai
, Che Ping Chuang

Department of Chemistry

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

46 Citations (Scopus)

Abstract

Oxidative free radical reactions of β-aminocinnamates are described. Imine radicals produced by tetra-n-butylammonium cerium(IV) nitrate (TBACN) oxidation of enamines undergo efficient addition to the C-C double bond of β-aminocinnamates. This TBACN mediated free radical reaction between β-aminocinnamates and enamines provides a novel method for the synthesis of highly substituted pyrroles. The direct TBACN oxidation of β- aminocinnamates gave the dimerization products effectively.

Original language	English
Pages (from-to)	2235-2239
Number of pages	5
Journal	Tetrahedron
Volume	62
Issue number	10
DOIs	https://doi.org/10.1016/j.tet.2005.12.011
Publication status	Published - 2006 Mar 6

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2005.12.011

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abstract = "Oxidative free radical reactions of β-aminocinnamates are described. Imine radicals produced by tetra-n-butylammonium cerium(IV) nitrate (TBACN) oxidation of enamines undergo efficient addition to the C-C double bond of β-aminocinnamates. This TBACN mediated free radical reaction between β-aminocinnamates and enamines provides a novel method for the synthesis of highly substituted pyrroles. The direct TBACN oxidation of β- aminocinnamates gave the dimerization products effectively.",

author = "Tsai, \{An I.\} and Chuang, \{Che Ping\}",

note = "Funding Information: We are grateful to the National Science Council of ROC for financial support. (Grant No. NSC-93-2113-M-006-004) ",

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T1 - Synthesis of highly substituted pyrroles via oxidative free radical reactions of β-aminocinnamates

AU - Tsai, An I.

AU - Chuang, Che Ping

N1 - Funding Information: We are grateful to the National Science Council of ROC for financial support. (Grant No. NSC-93-2113-M-006-004)

PY - 2006/3/6

Y1 - 2006/3/6

N2 - Oxidative free radical reactions of β-aminocinnamates are described. Imine radicals produced by tetra-n-butylammonium cerium(IV) nitrate (TBACN) oxidation of enamines undergo efficient addition to the C-C double bond of β-aminocinnamates. This TBACN mediated free radical reaction between β-aminocinnamates and enamines provides a novel method for the synthesis of highly substituted pyrroles. The direct TBACN oxidation of β- aminocinnamates gave the dimerization products effectively.

AB - Oxidative free radical reactions of β-aminocinnamates are described. Imine radicals produced by tetra-n-butylammonium cerium(IV) nitrate (TBACN) oxidation of enamines undergo efficient addition to the C-C double bond of β-aminocinnamates. This TBACN mediated free radical reaction between β-aminocinnamates and enamines provides a novel method for the synthesis of highly substituted pyrroles. The direct TBACN oxidation of β- aminocinnamates gave the dimerization products effectively.

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DO - 10.1016/j.tet.2005.12.011

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JO - Tetrahedron

JF - Tetrahedron

IS - 10

ER -

Synthesis of highly substituted pyrroles via oxidative free radical reactions of β-aminocinnamates

Abstract

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