Synthesis of 4-benzylidene-oxazol-5(4H)-imines, structural analogs of PK11195, under Bischler-Napieralski conditions

被引：3

作者：

Almaraz-Giron, Marco A. ^{[1
]}

Vazquez, Alfredo ^{[1
]}

机构：

[1] Univ Nacl Autonoma Mexico, Dept Quim Organ, Fac Quim, Ciudad Univ, Mexico City 04510, DF, Mexico

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 08期

关键词：

4-Benzylidene-oxazol-5(4H)imines; Bischler-Napieralski reaction; alpha; beta-Unsaturated acid derivatives; Oxazolones; PK11195; ANTIBACTERIAL ACTIVITY;

D O I：

10.1016/j.tetlet.2017.01.047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and convenient one-pot procedure to prepare 4-benzylidene-2-aryl-1,3-oxazol-5(4H)-imines from phenyl pyruvic acid and a series of arylamides, under classical Bischler-Napieralski (B-N) conditions and microwave heating (MW) has been developed. The structures of the prepared compounds were unambiguously assigned through single crystal X-ray diffraction studies. The compounds thus prepared can be used to synthesize bioactive compounds with different molecular architectures. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：785 / 788

页数：4

共 32 条

[1] Synthetic study on the T3P®-promoted one-pot preparation of 1-substituted-3,4-dihydro-β-carbolines by the reaction of tryptamine with carboxylic acids [J].

Abranyi-Balogh, Peter ;

Foldesi, Tamas ;

Grun, Alajos ;

Volk, Balazs ;

Keglevich, Gyorgy ;

Milen, Matyas .

TETRAHEDRON LETTERS, 2016, 57 (18) :1953-1957

[2]

Bala S., 2011, INT J CHEMTECH RES, V3, P1102

[3] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[4]

Bhusare S.R., 2003, Chem. Het. Comp, V39, P726

[5] SYNTHESIS OF N-(4-ARYLMETHYLENE-DELTA-2-OXAZOLIN-5-YLIDENE)AMMONIUM SALTS AND THEIR CONVERSION INTO 5-IMINO-DELTA2-OXAZOLINES AND 1,3-DIAZAFULVENES [J].

BOYD, GV ;

WRIGHT, PH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (9-10) :1140-&

[6]

COREY EJ, 1976, TETRAHEDRON LETT, P3

[7]

Dabholkar VV, 2012, HETEROCYCL LETT, V2, P405

[8]

Dabholkar W, 2012, RASAYAN J CHEM, V3, P761

[9] Abnormal products in the Bischler-Napieralski isoquinoline synthesis [J].

Doi, S ;

Shirai, N ;

Sato, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (15) :2217-2221

[10] PHOSPHORUS PENTOXIDE-METHANESULFONIC ACID - CONVENIENT ALTERNATIVE TO POLYPHOSPHORIC ACID [J].

EATON, PE ;

CARLSON, GR ;

LEE, JT .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (23) :4071-4073

← 1 2 3 4 →