SYNTHESIS OF NOVEL 2-METHYLSULFANYL-4H-[1,2,4] TRIAZOLO[1,5-a]QUINAZOLIN-5-ONE AND DERIVATIVES

被引：24

作者：

Al-Salahi, Rashad ^{[1
]}

Geffken, Detlef ^{[2
]}

机构：

[1] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia

[2] Univ Hamburg, Inst Pharm, Dept Chem, Hamburg, Germany

来源：

SYNTHETIC COMMUNICATIONS | 2011年 / 41卷 / 23期

关键词：

Alkylation; chlorination; dimethyl-N-cyanoimidodithiocarbonate; 2-hydrazinobenzoic acid; thionation; H-2-ANTIHISTAMINIC ACTIVITY; ACID; CYANOGUANIDINES; CHEMISTRY; THIOUREAS;

D O I：

10.1080/00397911.2010.518780

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

A novel 2-methylsulfanyl-4H-[1,2,4]triazolo[1,5-a] quinazolin-5-one was synthesized using dimethyl-n-cyanoimidodithiocarbonate and 2-hydrazinobenzoic acid as building blocks. Chemical transformation of the inherent lactam moiety in the targeted 2-methylsulfanyl-[1,2,4]triazolo[1,5-a] quinazolin-5-one offered access to a variety of derivatives.

引用

收藏

页码：3512 / 3523

页数：12

相关论文

共 27 条

[1]

Synthesis of Novel 2-Alkoxy(aralkoxy)-4H-[1,2,4]triazolo[1,5-a] quinazolin-5-ones Starting with Dialkyl-N-Cyanoimidocarbonates [J].

Al-Salahi, Rashad ;

Geffken, Detlef .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (03) :656-662

[2]

H-2-ANTIHISTAMINICS .7. SYNTHESIS AND H-2-ANTIHISTAMINIC ACTIVITY OF N,N-SUBSTITUTED THIOUREAS, CYANOGUANIDINES AND DITHIOOXAMIDES [J].

BARZEN, R ;

SCHUNACK, W .

ARCHIV DER PHARMAZIE, 1981, 314 (07) :617-622

[3]

Bereznak J.F., Preparation of fungicidal tricyclic 1,2,4-triazoles,, Patent No. [WO2008103357 A1, 2008103357]

[4]

BORCHERS A, 1982, ARZNEIMITTELFORSCH, V32-2, P1509

[5]

Unexpected hydrazinolysis behaviour of 1-chloro-4-methyl-5H-pyridazino[4,5-b]indole and a convenient synthesis of new[1,2,4]-triazolo [4′,3′:1,6]pyridazino[4,5-b]indoles [J].

El-Kashef, H ;

Farghaly, AAH ;

Haider, N ;

Wobus, A .

MOLECULES, 2004, 9 (10) :849-859

[6]

Structure-activity relationships for pyrido-, imidazo-, pyrazolo-, pyrazino-, and pyrrolophenazinecarboxamides as topoisomerase-targeted anticancer agents [J].

Gamage, SA ;

Spicer, JA ;

Rewcastle, GW ;

Milton, J ;

Sohal, S ;

Dangerfield, W ;

Mistry, P ;

Vicker, N ;

Charlton, PA ;

Denny, WA .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (03) :740-743

[7]

SYNTHESIS OF N-ALKYL-N'-CYANO-N''-4-PYRIDYLGUANIDINES FROM 4-PYRIDYLDITHIOCARBAMIC ACID VIA N-ALKYL-N'-4-PYRIDYLTHIOUREAS, OR VIA 4-PYRIDYLCYANIMINOTHIOCARBAMIC ACID [J].

HANSEN, ET ;

PETERSEN, HJ .

SYNTHETIC COMMUNICATIONS, 1984, 14 (13) :1275-1283

[8]

Hantzsch A, 1904, LIEBIGS ANN CHEM, V331, P265

[9]

CHEMISTRY OF 2H-3,1-BENZOXAZINE-2,4(1H)DIONE (ISATOIC ANHYDRIDES) .1. SYNTHESIS OF N-SUBSTITUTED 2H-3,1-BENZOXAZINE-2,4(1H)DIONES [J].

HARDTMANN, GE ;

KOLETAR, G ;

PFISTER, OR .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (03) :565-572

[10]

SYNTHESIS OF [1,2,4]TRIAZOLO[1,5-A]QUINAZOLINES - ASSIGNMENT OF THE CONFORMATION OF SUBSTITUENTS WITH THE AID OF C-13-NMR SPECTROSCOPY [J].

HECKENDORN, R ;

WINKLER, T .

HELVETICA CHIMICA ACTA, 1980, 63 (01) :1-9