[3+2] Cycloaddition of dimethyl acetylenedicarboxylate, methyl acrylate, and ethyl acrylate to 4,5-dihydro-5-methyl-3h-spiro[benz-2-azepine-3,1′- cyclohexane] N-oxide

被引：0

作者：

Varlamov A.V. ^{[1
]}

Chernyshev A.I. ^{[1
]}

Zubkov F.I. ^{[1
]}

Turchin K.F. ^{[2
]}

Levov A.N. ^{[1
]}

机构：

[1] Russ. People's Friendship University

[2] Pharmaceutical Chemical Center, All-Russ. Pharmaceutical Chem. Inst.

来源：

Chemistry of Heterocyclic Compounds | 2004年 / 40卷 / 3期

关键词：

3+2] cycloaddition; Benz-2-azepines; Cyclic nitrones; Monosubstituted alkenes;

D O I：

10.1023/B:COHC.0000028634.08685.99

中图分类号：

学科分类号：

摘要：

The cycloaddition of methyl acrylate and ethyl acrylate to 4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1′-cyclohexane] N-oxide proceeds without either regiospecificity or stereospecificity. Eight geometrical isomers of spiro[isoxazolidino[3,2-a]benz-2-azepine-5,1′-cyclohexane] were formed, of which several were isolated as pure samples. The cycloaddition of dimethyl acetylenedicarboxylate proceeds stereoselectively, leading to spiro[isoxazolino[3,2-a]benz-2-azepine-5,1′-cyclohexane] with cis arrangement of the protons at C(7) and C(11b).

引用

页码：364 / 369

页数：5

共 50 条

[1] Stereochemistry of [3+2]-cycloaddition of acrylonitrile to N-oxide of 4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1′-cyclohexane]
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[2] Regioselective addition of styrene to 4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1′-cyclohexane] N-oxide
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[3] Stereochemistry of the [3+2] cycloaddition of acrylonitrile to the N-oxide of 5-methyl-4,5-dihydro-3H-spiro[benz-2-azepine-3,1′-cyclohexane]
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[4] [3+2] Cycloaddition of acetylene dicarboxylic ether, methyl and ethyl acrylates to N-oxide of 4,5-dihydro-5-methyl-3H-spyro[benz-2-azepine-3,1′-cyclohexane]
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[5] Some chemical transformations of 4,5-dihydro-5-methyl-3H-spiro[benz-2- azepine-3,1'-cyclohexane] N-oxide
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[6] Some chemical transformations of 5-methyl-4,5-dihydro-3H-spiro[benz-2-azepine-3,1′-cyclohexane] N-oxide
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[7] Reactions of 4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3-cyclohexane] N-oxide with some nucleophilic reagents
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