Intramolecular cyclization of β-alkynylpropanamides to γ-alkylidene-γ-butyrolactams

被引：30

作者：

Koseki, Y ^{[1
]}

Kusano, S ^{[1
]}

Nagasaka, T ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Tokyo 1920392, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(98)00520-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method for the base-catalized intramolecular cyclization of beta-alkynylpropanamides 1 to gamma-alkylidene-gamma-butyrolactames 2 (and 3) was established. Reactions of beta-alkynylamides 1c-h, possessing alkyl groups at the terminal acetylenes, in the presence of a catalytic amount of LiN(TMS)(2)/AgOTf (= 2:1) in toluene gave exclusively (Z)-alkylidenelactames 2c-h in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3517 / 3520

页数：4

共 25 条

[1] 2-SUBSTITUTED-3-ACYLINDOLES THROUGH THE PALLADIUM-CATALYZED CARBONYLATIVE CYCLIZATION OF 2-ALKYNYLTRIFLUOROACETANILIDES WITH ARYL HALIDES AND VINYL TRIFLATES [J].

ARCADI, A ;

CACCHI, S ;

CARNICELLI, V ;

MARINELLI, F .

TETRAHEDRON, 1994, 50 (02) :437-452

[2]

Arcadi A, 1997, SYNLETT, P941

[3]

Bouyssi D, 1997, SYNLETT, P944

[4] SYNTHESIS OF MEDIUM RING ETHERS .3. DISPROOF OF THE PROPOSED 2,8-DISUBSTITUTED OXOCANE STRUCTURE FOR GLOEOSPORONE - SYNTHESIS OF PSEUDO-GLOEOSPORONE [J].

CARLING, RW ;

CLARK, JS ;

HOLMES, AB ;

SARTOR, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (01) :95-101

[5] PALLADIUM-CATALYZED INTRAMOLECULAR ADDITION OF AMINES TO ACETYLENES - SYNTHESIS OF CYCLIC IMINES [J].

FUKUDA, Y ;

MATSUBARA, S ;

UTIMOTO, K .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5812-5816

[6]

FUKUDA Y, 1987, HETEROCYCLES, V25, P297

[7] TETRAPYRROLES .4. A HIGHLY EFFICIENT SYNTHESIS OF HOMOCHIRAL DIHYDROPYRROMETHENONES VIA PD(0) MEDIATED COUPLING OF IODOPYRROLES AND ACETYLENIC AMIDES [J].

JACOBI, PA ;

RAJESWARI, S .

TETRAHEDRON LETTERS, 1992, 33 (42) :6235-6238

[8] Toward the synthesis of biologically important chlorins, isobacteriochlorins, and corrins. Cyclic enamides from acetylenic amides [J].

Jacobi, PA ;

Brielmann, HL ;

Hauck, SI .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :5013-5023

[9] Efficient synthesis of 4-ethenylidene-2-oxazolidinones via palladium-catalyzed aminocyclization of 2-butyn-1,4-diol biscarbamates [J].

Kimura, M ;

Wakamiya, Y ;

Horino, Y ;

Tamaru, Y .

TETRAHEDRON LETTERS, 1997, 38 (22) :3963-3966

[10]

KOSEKI Y, 1995, CHEM PHARM BULL, V43, P1604

← 1 2 3 →