A general synthesis of N-substituted 1,4-benzoxazine- and 1,4-benzothiazine-2-carboxylates via copper-catalyzed intramolecular amination of arylbromides

Ferdinand Melkonyan; Artiom Topolyan; Alexander Karchava; Marina Yurovskaya

doi:10.1016/j.tet.2011.06.081

A general synthesis of N-substituted 1,4-benzoxazine- and 1,4-benzothiazine-2-carboxylates via copper-catalyzed intramolecular amination of arylbromides

Ferdinand Melkonyan, Artiom Topolyan, Alexander Karchava^*, Marina Yurovskaya

^*Corresponding author for this work

Chemistry

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

22 Scopus citations

Abstract

Starting from ortho-bromosubstituted phenoxyacetates or (phenythio)acetates and primary amines, various N-substituted 4H-1,4-benzoxazine- and 4H-1,4-benzothiazine-2-carboxylates were synthesized in moderate to high yields by using a Cu(I)-catalyzed Ullmann-type cyclization as a key step. The method is simple to operate, tolerates many functional groups and does not require any additives.

Original language	English (US)
Pages (from-to)	6826-6832
Number of pages	7
Journal	Tetrahedron
Volume	67
Issue number	36
DOIs	https://doi.org/10.1016/j.tet.2011.06.081
State	Published - Sep 9 2011

Keywords

1,4-Benzothiazine
1,4-Benzoxazine
Copper-catalyzed reactions
Cyclization
Heterocycles
Ullmann amination reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2011.06.081

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title = "A general synthesis of N-substituted 1,4-benzoxazine- and 1,4-benzothiazine-2-carboxylates via copper-catalyzed intramolecular amination of arylbromides",

abstract = "Starting from ortho-bromosubstituted phenoxyacetates or (phenythio)acetates and primary amines, various N-substituted 4H-1,4-benzoxazine- and 4H-1,4-benzothiazine-2-carboxylates were synthesized in moderate to high yields by using a Cu(I)-catalyzed Ullmann-type cyclization as a key step. The method is simple to operate, tolerates many functional groups and does not require any additives.",

keywords = "1,4-Benzothiazine, 1,4-Benzoxazine, Copper-catalyzed reactions, Cyclization, Heterocycles, Ullmann amination reaction",

author = "Ferdinand Melkonyan and Artiom Topolyan and Alexander Karchava and Marina Yurovskaya",

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T1 - A general synthesis of N-substituted 1,4-benzoxazine- and 1,4-benzothiazine-2-carboxylates via copper-catalyzed intramolecular amination of arylbromides

AU - Melkonyan, Ferdinand

AU - Topolyan, Artiom

AU - Karchava, Alexander

AU - Yurovskaya, Marina

PY - 2011/9/9

Y1 - 2011/9/9

N2 - Starting from ortho-bromosubstituted phenoxyacetates or (phenythio)acetates and primary amines, various N-substituted 4H-1,4-benzoxazine- and 4H-1,4-benzothiazine-2-carboxylates were synthesized in moderate to high yields by using a Cu(I)-catalyzed Ullmann-type cyclization as a key step. The method is simple to operate, tolerates many functional groups and does not require any additives.

AB - Starting from ortho-bromosubstituted phenoxyacetates or (phenythio)acetates and primary amines, various N-substituted 4H-1,4-benzoxazine- and 4H-1,4-benzothiazine-2-carboxylates were synthesized in moderate to high yields by using a Cu(I)-catalyzed Ullmann-type cyclization as a key step. The method is simple to operate, tolerates many functional groups and does not require any additives.

KW - 1,4-Benzothiazine

KW - 1,4-Benzoxazine

KW - Copper-catalyzed reactions

KW - Cyclization

KW - Heterocycles

KW - Ullmann amination reaction

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DO - 10.1016/j.tet.2011.06.081

M3 - Article

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JO - Tetrahedron

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ER -

A general synthesis of N-substituted 1,4-benzoxazine- and 1,4-benzothiazine-2-carboxylates via copper-catalyzed intramolecular amination of arylbromides

Abstract

Keywords

ASJC Scopus subject areas

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