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
AIDHEN, IS
NARASIMHAN, NS
[J]. 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
COLLADO, MI
LETE, E
SOTOMAYOR, N
VILLA, MJ
[J]. TETRAHEDRON, 1995, 51 (16) : 4701 - 4710
[3] ASYMMETRIC-SYNTHESIS OF BENZOQUINOLIZIDINES - A FORMAL SYNTHESIS OF (-)-EMETINE
GUILES, JW
MEYERS, AI
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) : 6873 - 6878
[4] AROMATIC HETEROANNULATION VIA ORTHO-LITHIATION-CYCLIZATION OF N-ACYL-2-BROMOBENZAMIDES
HENDI, MS
NATALIE, KJ
HENDI, SB
CAMPBELL, JA
GREENWOOD, TD
WOLFE, JF
[J]. 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
KANO, S
YUASA, Y
SHIBUYA, S
[J]. 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
KOBOR, J
SOHAR, P
FULOP, F
[J]. 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
Lete, E
Collado, MI
Sotomayor, N
Vicente, T
Villa, MJ
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (06) : 1751 - 1758

← 1 2 →