Studies on inverse electron demand hetero Diels-Alder reaction of perfluoroalkyl 2(1H) pyridones with different dienophiles under microwave irradiation

被引：12

作者：

Krishnaiah, A ^{[1
]}

Narsaiah, B ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 2, Hyderabad 500007, Andhra Pradesh, India

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2002年 / 113卷 / 01期

关键词：

N-substituted 2(1H) pyridones; DMAD; N-adducts;

D O I：

10.1016/S0022-1139(01)00494-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reaction of N-acetyl perfluoroalkyl substituted 2(1H) pyridones (7) with dimethylacetylenedicarboxylate (DMAD) on neutral alumina under solvent free microwave irradiation conditions extended to undergo an inverse electron demand hetero Diels-Alder reaction, however resulted exclusively in E, Z isomers (3:1) of Michael-type N-adducts (8). The similar reaction in case of 7a under thermal and photochemical conditions also gave the same products. (C) 2002 Elsevier Science B.V. All rights reserved.

引用

页码：133 / 137

页数：5

共 14 条

[1]

AFRINKIA K, 1992, TETRAHEDRON, V48, P9111

[2] STUDIES OF AROMATICITY BY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY .1. 2-PYRIDONES AND RELATED SYSTEMS [J].

ELVIDGE, JA ;

JACKMAN, LM .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (MAR) :859-&

[3] REACTION OF ALPHA PYRIDONES WITH ACETYLENE DICARBONIC ACID DIMETHYL ESTER [J].

HEEP, U .

TETRAHEDRON, 1975, 31 (01) :77-80

[4]

JURE M, 1987, AKAD VESTIS KIM SER, P627

[5] DIELS-ALDER CYCLOADDITIONS OF 2(1H)-PYRIDONES HAVING AN ELECTRON-WITHDRAWING GROUP [J].

NAKANO, H ;

TOMISAWA, H ;

HONGO, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (24) :1775-1776

[6] AN IMPROVED SYNTHETIC ROUTE TO TRIFLUOROMETHYL-6-SUBSTITUTED-2(1H)-PYRIDONES [J].

NARSAIAH, B ;

SIVAPRASAD, A ;

VENKATARATNAM, RV .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1993, 25 (01) :116-117

[7] SYNTHESIS OF NOVEL 2,7-DISUBSTITUTED-3-AMINO-9-TRIFLUOROMETHYL-4-OXO-4H-PYRIDO-[3',2'/4,5]-FURO-[3,2-D]-(1,3)-PYRIMIDINES [J].

NARSAIAH, B ;

SIVAPRASAD, A ;

VENKATARATNAM, RV .

JOURNAL OF FLUORINE CHEMISTRY, 1994, 69 (02) :139-143

[8] FLUORINATED NITROGEN HETEROCYCLES VIA CYCLIZATION .I. TRIFLUOROMETHYL-2-PYRIDONES FROM FLUORINATED 1.3-DICARBONYLS AND CYANOACETAMIDE [J].

PORTNOY, S .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (10) :3377-&

[9]

Reddy ACS, 1996, J FLUORINE CHEM, V78, P21

[10]

REDDY ACS, 1996, TETRAHEDRON LETT, V27, P21

← 1 2 →