A Facile Regioselective Synthesis of Novel Spiroacenaphthene Pyrroloisoquinolines Through 1,3-Dipolar Cycloaddition Reactions

被引：6

作者：

Sarrafi, Yaghoub ^{[1
]}

Asghari, Asieh ^{[1
]}

Hamzehloueian, Mahshid ^{[2
]}

Alimohammadi, Kamal ^{[3
]}

Sadatshahabi, Marzieh ^{[1
]}

机构：

[1] Univ Mazandaran, Fac Chem, Dept Organ Chem, Babol Sar 47416, Iran

[2] Islamic Azad Univ, Jouybar Branch, Dept Chem, Jouybar, Iran

[3] Univ Farhangian, Dr Shariati Branch, Dept Chem, Sari, Iran

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2013年 / 24卷 / 12期

关键词：

1,3-dipolar cycloaddition; azomethine ylide; 1,5]-H shift; spiroacenaphthene pyrroloisoquinolines; AZOMETHINE YLIDE CYCLOADDITION; CONSTRUCTION; AZIRIDINES;

D O I：

10.5935/0103-5053.20130245

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient one-pot three-component procedure for the synthesis of novel spiroacenaphthene pyrroloisoquinolines with high regioselectivity is described. These compounds were prepared from 1,3-dipolar cycloaddition of an azomethine ylide generated from acenaphthenequinone and 1,2,3,4-tetrahydroisoquinoline via [1,5]-H shift, with chalcone and nitrostyrene derivatives as dipolarophiles. The structure and stereochemistry of the cycloadducts have been established by single crystal X-ray structure and spectroscopic techniques.

引用

页码：1957 / +

页数：64

共 50 条

[41] SYNTHESIS AND 1,3-DIPOLAR CYCLOADDITION REACTIONS OF 2-METHYLENECEPHALOSPORINS
JANOS, P
CSABA, JJ
GYULA, B
FERENC, S
KATALIN, EK
MAGYAR KEMIAI FOLYOIRAT, 1991, 97 (05): : 196 - 205
[42] Synthesis of spiroisoxazolines by 1,3-dipolar cycloaddition
Micuch, P
Fisera, L
Ondrus, V
Ertl, P
MOLECULES, 1997, 2 (03) : 57 - 61
[43] Novel One Pot Regioselective Multicomponent Synthesis of Highly Functionlaized Spiro Pyrrolidines Through 1,3-Dipolar Cycloaddition Approach
Kathiravan, Subban
Raghunathan, Raghavachary
SYNTHETIC COMMUNICATIONS, 2013, 43 (07) : 1041 - 1054
[44] EXPEDIENT APPROACH FOR THE SYNTHESIS OF TRISPIROPYRROLIDINE BISOXIN DOLES THROUGH 1,3-DIPOLAR CYCLOADDITION REACTIONS
Feng, Guo-Liang
Li, Yue
Geng, Li-Jun
Zhang, Hong-Li
Shi, Yan-Jing
Wang, Kai-Fang
SYNTHETIC COMMUNICATIONS, 2015, 45 (10) : 1259 - 1268
[45] ORGANOPHOSPHORUS COMPOUNDS IN 1,3-DIPOLAR CYCLOADDITION REACTIONS
KHUSAINOVA, NG
PUDOVIK, AN
USPEKHI KHIMII, 1978, 47 (09) : 1507 - 1527
[46] Regioselective synthesis of 1,2,3-triazole derivatives via 1,3-dipolar cycloaddition reactions in water
Wang, ZX
Qin, HL
CHEMICAL COMMUNICATIONS, 2003, (19) : 2450 - 2451
[47] 1,3-dipolar cycloaddition of nitrile imines in the chemoselective and regioselective synthesis of heterocycles.
Oh, LM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U113 - U113
[48] Studies on intramolecular 1,3-dipolar cycloaddition reactions——Ⅲ. The synthesis of a novel heterocyclic ring system by regiospecific cycloaddition
CHEN Qing-Hua*
YU Xiu-Zhi
ZHANG Tie-Yuan
JIA Xi-Bei
ActaChimicaSinica(EnglishEdition), 1989, (02) : 176 - 182
[49] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF ISOCYANATES AND ISOTHIOCYANATES
VANLOOCK, E
INDUSTRIE CHIMIQUE BELGE-BELGISCHE CHEMISCHE INDUSTRIE, 1974, 38 (7-8): : 661 - 686
[50] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF A HETEROCYCLIC NITRONE
ALI, SA
ALMUALLEM, HA
TETRAHEDRON, 1992, 48 (25) : 5273 - 5282

← 1 2 3 4 5 →