Utilization of α-halocarbonyl compounds in the synthesis of thiazole, thiadiazole, and thiophene derivatives

被引：26

作者：

Abdel-Latif, Ehab ^{[1
]}

Bondock, Samir ^{[1
]}

机构：

[1] Mansoura Univ, Fac Sci, Dept Chem, Mansoura 35516, Egypt

来源：

HETEROATOM CHEMISTRY | 2006年 / 17卷 / 04期

关键词：

D O I：

10.1002/hc.20206

中图分类号：

O6 [化学];

学科分类号：

0703 [化学];

摘要：

The behavior of ethyl 2-phenylthiocarb-amoyl acetate 1 toward a variety of several alpha-halo-arbonyl compounds was investigated. Thus, reaction of I with alpha-bromoketones, hydrazonoyl bromides, and 2-chloro-N-arylacetamides afforded the corresponding dihydrothiazole, 1,3,4-thiadiazole, and thiophene derivatives, respectively. The synthesis of thiazolidin-4-one 11, thiazolidin-5-one 12, and some azo derivatives of thiazolidin-5-one were described. 5-Atylazothiazoles 17 and 19 were synthesized by condensation of hydrazonoyl bromides 3 with different thiourea derivatives. (c) 2006 Wiley Periodicals, Inc.

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页码：299 / 305

页数：7

相关论文

共 25 条

[1]

New orally active non-peptide fibrinogen receptor (GpIIb-IIIa) antagonists: Identification of ethyl 3-[N-[4-[4-[amino[(ethoxycarbonyl)imino]methyl]phenyl]-1,3-thiazol-2-yl]-N-[1-[(ethoxycarbonyl)methyl]piperid-4-yl]amino]propionate (SR 121787) as a potent and long-acting antithrombotic agent [J].

Badorc, A ;

Bordes, MF ;

deCointet, P ;

Savi, P ;

Bernat, A ;

Lale, A ;

Petitou, M ;

Maffrand, JP ;

Herbert, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (21) :3393-3401

[2]

BARNIKOW G, 1966, LIEBIGS ANN CHEM, V695, P49

[3]

PHENETHYLTHIAZOLETHIOUREA (PETT) COMPOUNDS, A NEW CLASS OF HIV-1 REVERSE-TRANSCRIPTASE INHIBITORS .1. SYNTHESIS AND BASIC STRUCTURE-ACTIVITY RELATIONSHIP STUDIES OF PETT ANALOGS [J].

BELL, FW ;

CANTRELL, AS ;

HOGBERG, M ;

JASKUNAS, SR ;

JOHANSSON, NG ;

JORDAN, CL ;

KINNICK, MD ;

LIND, P ;

MORIN, JM ;

NOREEN, R ;

OBERG, B ;

PALKOWITZ, JA ;

PARRISH, CA ;

PRANC, P ;

SAHLBERG, C ;

TERNANSKY, RJ ;

VASILEFF, RT ;

VRANG, L ;

WEST, SJ ;

ZHANG, H ;

ZHOU, XX .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (25) :4929-4936

[4]

Synthesis and activity of sulfonamide-substituted 4,5-diaryl thiazoles as selective cyclooxygenase-2 inhibitors [J].

Carter, JS ;

Kramer, S ;

Talley, JJ ;

Penning, T ;

Collins, P ;

Graneto, MJ ;

Seibert, K ;

Koboldt, CM ;

Masferrer, J ;

Zweifel, B .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (08) :1171-1174

[5]

4-HYDROXY-3-QUINOLINECARBOXAMIDES WITH ANTIARTHRITIC AND ANALGESIC ACTIVITIES [J].

CLEMENCE, F ;

LEMARTRET, O ;

DELEVALLEE, F ;

BENZONI, J ;

JOUANEN, A ;

JOUQUEY, S ;

MOUREN, M ;

DERAEDT, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (07) :1453-1462

[6]

2,4-disubstituted thiazoles .2. A novel class of antitumor agents, synthesis and biological evaluation [J].

ElSubbagh, H ;

AlObaid, AM .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1996, 31 (12) :1017-1021

[7]

The chemistry of α-haloketones and their utility in heterocyclic synthesis [J].

Erian, AW ;

Sherif, SM ;

Gaber, HM .

MOLECULES, 2003, 8 (11) :793-865

[8]

GOLDSTEIN BM, 1991, BLOOD, V78, P593

[9]

N-(4-SUBSTITUTED-THIAZOLYL)OXAMIC ACID-DERIVATIVES, A NEW SERIES OF POTENT, ORALLY ACTIVE ANTIALLERGY AGENTS [J].

HARGRAVE, KD ;

HESS, FK ;

OLIVER, JT .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (08) :1158-1163

[10]

SYNTHESIS OF ETHYL ALPHA-PHENYLTHIOCARBAMYLGLYOXALATE ARYLHYDRAZONES AND THEIR REACTIONS WITH HYDRAZINES [J].

HARHASH, AH ;

KADERAMER, FA ;

ELDIN, MAFN ;

AWAD, ML .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1976, 31 (06) :846-849