Parham-type cyclization and nucleophilic addition-N-acyliminium ion cyclization sequences for the construction of the isoquinoline nucleus

被引：29

作者：

Collado, MI ^{[1
]}

Sotomayor, N ^{[1
]}

Villa, MJ ^{[1
]}

Lete, E ^{[1
]}

机构：

[1] UNIV BASQUE COUNTRY, FAC CIENCIAS, DEPT QUIM ORGAN, BILBAO 48080, SPAIN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 34期

关键词：

D O I：

10.1016/0040-4039(96)01321-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient methodologies based on the nucleophilic addition-N-acyliminium ion cyclization and the Parham-type cyclization sequences of N-phenethylimides 1 and 2 are reported for the synthesis of a variety of heterocyclic systems: benzo[a]quinolizidones and their 2-oxa analogs, isoindoloisoquinolones, dibenzo[a,h]quinolizidones, thiazolo-, oxazolo-, and imidazolo [4,3-a]isoquinolones. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：6193 / 6196

页数：4

共 12 条

[1] A NOVEL AND VERSATILE SYNTHESIS OF 1-ARYL-BENZOCYCLOBUTENOLS AND 1-ARYL-BENZOCYCLOBUTENES [J].

AIDHEN, IS ;

NARASIMHAN, NS .

TETRAHEDRON LETTERS, 1991, 32 (19) :2171-2172

[2] SYNTHESIS OF 5-ARYLPYRROLO[2,1-A]ISOQUINOLIN-3(2H)-ONES FROM N-PHENETHYLSUCCINIMIDES AND ORGANOLITHIUM REAGENTS [J].

COLLADO, MI ;

LETE, E ;

SOTOMAYOR, N ;

VILLA, MJ .

TETRAHEDRON, 1995, 51 (16) :4701-4710

[3] ASYMMETRIC-SYNTHESIS OF BENZOQUINOLIZIDINES - A FORMAL SYNTHESIS OF (-)-EMETINE [J].

GUILES, JW ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6873-6878

[4] AROMATIC HETEROANNULATION VIA ORTHO-LITHIATION-CYCLIZATION OF N-ACYL-2-BROMOBENZAMIDES [J].

HENDI, MS ;

NATALIE, KJ ;

HENDI, SB ;

CAMPBELL, JA ;

GREENWOOD, TD ;

WOLFE, JF .

TETRAHEDRON LETTERS, 1989, 30 (03) :275-278

[5]

Hiemstra H., 1991, COMPREHENSIVE ORGANI, V2, P1047

[6]

Hiemstra H., 1988, ALKALOIDS, V32, P271

[7] A SYNTHESIS OF HETEROCYCLIC FUSED ISOQUINOLINES THROUGH N-ACYLIMINIUM ION INTERMEDIATES [J].

KANO, S ;

YUASA, Y ;

SHIBUYA, S .

SYNTHETIC COMMUNICATIONS, 1985, 15 (10) :883-889

[8] SYNTHESIS AND STEREOCHEMICAL STUDY OF CIS-1-(3'-SUBSTITUTED-PROPYL)BENZO[A]QUINOLIZIDINE AND TRANS-1-(3'-SUBSTITUTED-PROPYL)BENZO[A]QUINOLIZIDINE [J].

KOBOR, J ;

SOHAR, P ;

FULOP, F .

TETRAHEDRON, 1994, 50 (16) :4873-4886

[9]

LETE E, 1993, SYNLETT, P41

[10] Application of the ortho-lithiation-cyclization strategy to N-benzyl- and N-phenethylamine derivatives [J].

Lete, E ;

Collado, MI ;

Sotomayor, N ;

Vicente, T ;

Villa, MJ .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (06) :1751-1758

← 1 2 →