Synthesis of 3,4-dihydroquinazolin-4-one:: selenium-catalyzed reductive N-heterocyclization of N-(2-nitrobenzoyl)amides with carbon monoxide

被引:28
作者
Nishiyama, Y [1 ]
Hirose, M [1 ]
Kitagaito, W [1 ]
Sonoda, N [1 ]
机构
[1] Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan
关键词
D O I
10.1016/S0040-4039(02)00035-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A catalytic synthetic method of 3,4-dihydroquinazolin-4-ones has been developed. When N-(2-nitrobenzoyl)amides were treated with carbon monoxide in the presence of a catalytic amount of selenium, reductive N-heterocyclization of N-(2-nitrobenzoyl)amide efficiently proceeded to give the corresponding 3,4-dihydroquinazolin-4-ones in moderate to good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1855 / 1858
页数:4
相关论文
共 13 条
[1]   TRANSITION-METAL COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION - SYNTHESIS OF 4(3H)-QUINAZOLINONE DERIVATIVES FROM N-(2-NITROBENZOYL)AMIDES [J].
AKAZOME, M ;
KONDO, T ;
WATANABE, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :310-312
[2]   ALAKLOIDS OF ANISOTES SESSILIFLORUS CBCL (ACANTHACEAE) - 5 NEW 4-QUINAZOLONE ALKALOIDS [J].
ARNDT, RR ;
EGGERS, SH ;
JORDAAN, A .
TETRAHEDRON, 1967, 23 (08) :3521-&
[3]   A synthesis of rut oe carpine. [J].
Asahina, Y ;
Manske, RHF ;
Robinson, R .
JOURNAL OF THE CHEMICAL SOCIETY, 1927, :1708-1710
[4]   THE STRUCTURE AND PROPERTIES OF SOME INDOLIC CONSTITUENTS IN COUROUPITA-GUIANENSIS AUBL [J].
BERGMAN, J ;
LINDSTROM, JO ;
TILSTAM, U .
TETRAHEDRON, 1985, 41 (14) :2879-2881
[5]   Synthesis of novel carbopolycycles and heterocycles. 41. Synthesis of optically active vasicinone based on intramolecular aza-Wittig reaction and asymmetric oxidation [J].
Eguchi, S ;
Suzuki, T ;
Okawa, T ;
Matsushita, Y ;
Yashima, E ;
Okamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7316-7319
[6]   ANTI-MICROBIAL SPECIFICITY OF TRYPTANTHRIN [J].
HONDA, G ;
TABATA, M ;
TSUDA, M .
PLANTA MEDICA, 1979, 37 (02) :172-174
[7]   ISOLATION OF ANTIFUNGAL PRINCIPLE TRYPTANTHRIN, FROM STROBILANTHES-CUSIA KUNTZE,O. [J].
HONDA, G ;
TABATA, M .
PLANTA MEDICA, 1979, 36 (01) :85-86
[8]   ALKALOIDS .142. NEW ALKALOIDS FROM ADHATODA-VASICA NEES [J].
JOHNE, S ;
GROGER, D ;
HESSE, M .
HELVETICA CHIMICA ACTA, 1971, 54 (03) :826-&
[9]   NEW SYNTHESIS OF CARBONYL SELENIDE [J].
KONDO, K ;
YOKOYAMA, S ;
MIYOSHI, N ;
MURAI, S ;
SONODA, N .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (09) :691-691
[10]   VASICINONE - A BRONCHODILATOR PRINCIPLE FROM ADHATODA VASICA NES (NOACANTHACEAE) [J].
MEHTA, DR ;
NARAVANE, JS ;
DESAI, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) :445-&