One-pot synthesis of simple alkaloids: 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine

被引：66

作者：

Jahng, Katherine Chae ^{[1
]}

Kim, Seung Ill ^{[1
]}

Kim, Dong Hyeon ^{[1
]}

Seo, Chang Seob ^{[1
]}

Son, Jong-Keun ^{[1
]}

Lee, Seung Ho ^{[1
]}

Lee, Eung Seok ^{[1
]}

Jahng, Yurngdong ^{[1
]}

机构：

[1] Yeungnam Univ, Coll Pharm, Kyongsan 712749, South Korea

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2008年 / 56卷 / 04期

关键词：

deoxyvasicinone; mackinazolinone; luotonin A; tryptanthrin; rutaecarpine; anthranilic acid;

D O I：

10.1248/cpb.56.607

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

One-pot synthesis of various 2,3-polymethylene-4(3H)-quinazolinones from anthranilic acid, corresponding lactam and SOCl2 is described, which can be applicable to the synthesis of simple 4(3H)-quinazolinone-derived alkaloids, such as luotonin A, tryptanthrin, and rutaecarpine.

引用

页码：607 / 609

页数：3

共 51 条

[1] TRYPTAMINES, CARBOLINES, AND RELATED COMPOUNDS .2. A CONVENIENT SYNTHESIS OF TRYPTAMINES AND BETA-CARBOLINES [J].

ABRAMOVITCH, RA ;

SHAPIRO, D .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (NOV) :4589-4592

[2] 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

[3] BRONCHODILATOR ALKALOID (VASICINONE) FROM ADHATODA-VASICA NEES [J].

AMIN, AH ;

MEHTA, DR .

NATURE, 1959, 184 (4695) :1317-1317

[4]

ANNAREGO WLF, 1967, FUSED PYRIMIDINES, P89

[5] A synthesis of rut oe carpine. [J].

Asahina, Y ;

Manske, RHF ;

Robinson, R .

JOURNAL OF THE CHEMICAL SOCIETY, 1927, :1708-1710

[6]

Asahina Y., 1915, J. Pharm. Soc. Jpn., V35, P1293

[7]

BERGMAN J, 1977, TETRAHEDRON LETT, P2625

[8] STUDIES OF RUTAECARPINE AND RELATED QUINAZOLINOCARBOLINE ALKALOIDS [J].

BERGMAN, J ;

BERGMAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1246-1255

[9]

Bergman J., 1983, the Alkaloids: Chemistry and Pharmacology, V21, P29

[10] Radical reactions with 3H-quinazolin-4-ones:: synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin [J].

Bowman, W. Russell ;

Elsegood, Mark R. J. ;

Stein, Tobias ;

Weaver, George W. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (01) :103-113

← 1 2 3 4 5 6 →