Synthesis of fused bicyclic glutarimides

被引：10

作者：

Chang, MY ^{[1
]}

Chen, CY

Chen, ST

Chang, NC

机构：

[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan

[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

[3] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan

来源：

TETRAHEDRON | 2003年 / 59卷 / 38期

关键词：

bicyclic glutarimides; stepwise [3+3] annulation; intramolecular alkylation; oxidative cyclization or ring-closing metathesis;

D O I：

10.1016/S0040-4020(03)01198-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe an efficient route towards the synthesis of fused bicyclic glutarimides using facile [3+3] reaction of alpha-sulfonylacetamides with different alpha,beta-unsaturated esters as the key step. Intramolecular cyclization of 4-substituted 3-sulfonylglutarimide to form 5,6-, 6,6- or 6,7-fused bicyclic glutarimides was accomplished via alkylation, oxidative cyclization or ring-closing metathesis in modest yield. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：7547 / 7553

页数：7

共 46 条

[1] Resolution of 4 cyano-4-(4-nitrophenyl)hexanoic acid: Synthesis of (R) and (S)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione (aminoglutethimide) [J].

Achmatowicz, O ;

Malinowska, I ;

Szechner, B ;

Maurin, JK .

TETRAHEDRON, 1997, 53 (23) :7917-7928

[2]

Armstrong SK, 1998, J CHEM SOC PERK T 1, P371

[3]

Baxter E.W., 1992, ALKALOIDS CHEM BIOL, V8, P197

[4] The synthesis of (±)-aminoglutethimide via vicarious nucleophilic aromatic substitution of hydrogen [J].

Bushell, SM ;

Crump, JP ;

Lawrence, NJ ;

Pineau, G .

TETRAHEDRON, 1998, 54 (10) :2269-2274

[5] Regioselective reduction of N-alkyl-3-sulfonyl glutarimides.: Synthesis of 3,4-dihydro-3-tosylpyridin-2-ones [J].

Chang, BR ;

Chen, CY ;

Chang, NC .

TETRAHEDRON LETTERS, 2002, 43 (17) :3233-3235

[6]

Chang MY, 2002, HETEROCYCLES, V57, P2321

[7]

Chang MY, 2003, HETEROCYCLES, V60, P99

[8] A synthesis of racemic thalidomide [J].

Chang, MY ;

Chen, ST ;

Chang, NC .

SYNTHETIC COMMUNICATIONS, 2003, 33 (08) :1375-1382

[9] Synthetic study of 4-substituted piperidine ring in elarofiban, RWJ-50042, tirofiban and paroxetine [J].

Chang, MY ;

Lin, JYC ;

Chen, ST ;

Chang, NC .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2002, 49 (06) :1079-1088

[10] 1,8-diazabicyclo[5.4.0]undec-7-ene:: A remarkable base in the debromination of 4-or 5-substituted N-benzyl α-bromo-α-p-toluenesulfonylglutarimide [J].

Chang, MY ;

Lin, JYC ;

Chen, ST ;

Chang, NC .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2002, 49 (06) :1015-1024

← 1 2 3 4 5 →