A facile synthesis of C2,N3-disubstituted-4-quinazolone

被引：81

作者：

Xue, S ^{[1
]}

McKenna, J ^{[1
]}

Shieh, WC ^{[1
]}

Repic, J ^{[1
]}

机构：

[1] Novartis Inst Biomed Res, Chem & Analyt Dev, E Hanover, NJ 07936 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 19期

关键词：

D O I：

10.1021/jo049118e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient methodology for the synthesis Of C-2,N-3-disubstituted-4 quinazolones from anilines and N-acylanthranilic acids was developed. The new cyclization conditions are much milder than any other reported protocols and resulted in excellent yields (87-98%) without chromatography.

引用

页码：6474 / 6477

页数：4

共 20 条

[1] SYNTHESIS AND CENTRAL NERVOUS-SYSTEM ACTIVITY OF QUINAZOLONES RELATED TO 2-METHYL-3-(ORTHO-TOLYL)-4(3H)-QUINAZOLONE (METHAQUALONE) [J].

AGER, IR ;

HARRISON, DR ;

KENNEWELL, PD ;

TAYLOR, JB .

JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (03) :379-386

[2] Synthesis of quinazolin-4-(3H)-ones from o-amidobenzonitriles using urea hydrogen peroxide [J].

Bandgar, BP .

SYNTHETIC COMMUNICATIONS, 1997, 27 (12) :2065-2068

[3] A facile route to quinazolin-4(3H)-ones functionalised at the 2-position [J].

Bavetsias, V .

SYNTHETIC COMMUNICATIONS, 1998, 28 (24) :4547-4559

[4] SYNTHESIS OF CHRYSOGINE, A METABOLITE OF PENICILLIUM-CHRYSOGENUM AND SOME RELATED 2-SUBSTITUTED 4-(3H)-QUINAZOLINONES [J].

BERGMAN, J ;

BRYNOLF, A .

TETRAHEDRON, 1990, 46 (04) :1295-1310

[5]

CHENARD BL, 1998, Patent No. 0884310

[6]

GEORGE T, 1971, INDIAN J CHEM, V9, P1077

[7] PHOSPHAZO COMPOUNDS AND THEIR USE IN PREPARING AMIDES [J].

GRIMMEL, HW ;

GUENTHER, A ;

MORGAN, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (04) :539-542

[8]

GUJRAL M. L., 1955, INDIAN JOUR MED RES, V43, P637

[9] Quinazoline antifolates thymidylate synthase inhibitors: Lipophilic analogues with modification to the C2-methyl substituent [J].

Hennequin, LF ;

Boyle, FT ;

Wardleworth, JM ;

Marsham, PR ;

Kimbell, R ;

Jackman, AL .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (03) :695-704

[10] ANTIHYPERTENSIVE 2-AMINO-4(3H)-QUINAZOLINONES [J].

HESS, HJ ;

CRONIN, TH ;

SCRIABINE, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (01) :130-+

← 1 2 →