An efficient regioselective synthesis of highly functionalized 3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidines via an isocyanide-based three-component reaction

被引:24
作者
Esmaeili, Abbas Ali [1 ,2 ]
Zangouei, Mandieh [1 ]
Fakhari, Ali Reza [3 ]
Habibi, Azizollah [4 ]
机构
[1] Univ Birjand, Dept Chem, Birjand, Iran
[2] Ferdowsi Univ Mashhad, Dept Chem, Mashhad, Iran
[3] Shahid Beheshti Univ, Fac Sci, Dept Chem, GC, Tehran, Iran
[4] Univ Tarbiatmoallem, Fac Chem, Tehran 1571914911, Iran
关键词
2-Imino-1,3-thiazolidin-4-one; Dialkyl acetylenedicarboxylates; Alkyl isocyanides; Thiazolo[3,2-a]pyrimidine; ASSISTED COMBINATORIAL SYNTHESIS; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; CONVENIENT SYNTHESIS; DERIVATIVES; THIAZOLOPYRIMIDINES; PYRIMIDINE; LIBRARIES; ROUTE; ACID;
D O I
10.1016/j.tetlet.2012.01.005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We present a novel, convenient, and efficient method for synthesizing polysubstituted 3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidines via a three-component reaction. The zwitterions generated from the reaction of isocyanides and dialkyl acetylenedicarboxylates react with 2-imino-1,3-thiazolidin-4-one to produce the title compounds in good yields. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1351 / 1353
页数:3
相关论文
共 50 条
[31]   Synthesis and Antimicrobial Activity of N-5-Diaryl-7-Methyl-3-OXO-2,3-Dihydro-5H-[1,3]Thiazolo[3,2-a]Pyrimidine-6-Carboxamide Hydrochlorides [J].
Gein, V. L. ;
Zamaraeva, T. M. ;
Buzmakova, N. A. ;
Odegova, T. F. ;
Gein, L. F. .
PHARMACEUTICAL CHEMISTRY JOURNAL, 2015, 49 (08) :512-514
[32]   When Serendipity Knocks on the Door: Synthesis and Physicochemical Characterization of 7-Chloro-2,3-dihydro-5H-thiazolo[3,2-α]pyrimidin-5-one [J].
Carmona-Vargas, Christian C. ;
Ellena, Javier ;
D'Vries, Richard F. ;
Chaur, Manuel N. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2019, 30 (07) :1475-1482
[33]   Synthesis and Crystal Structure of Ethyl 5-(4-Bromophenyl)-7-methyl-3-oxo-2,3-dihidro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate [J].
Agarkov, Artem ;
Nefedova, Anna ;
Ovsyannikov, Alexander ;
Litvinov, Igor ;
Solovieva, Svetlana ;
Antipin, Igor .
MOLBANK, 2023, 2023 (01)
[34]   An Efficient One-pot Three-component Method for the Synthesis of 5-Amino-3-(2-oxo-2H-chromen-3-yl)-7-aryl-7H-thiazolo[3,2-a]pyridine-6,8-dicarbonitriles [J].
Kotthireddy, Kavitha ;
Devulapally, Srikrishna ;
Dubey, Pramod Kumar ;
Pasula, Aparna .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (03) :938-946
[35]   Microwave-Assisted Regioselective Synthesis of 3-Functionalized Indole Derivatives via Three-Component Domino Reaction [J].
Lin, Wei ;
Zheng, Yong-Xiang ;
Xun, Zhan ;
Huang, Zhi-Bin ;
Shi, Da-Qing .
ACS COMBINATORIAL SCIENCE, 2017, 19 (11) :708-713
[36]   Synthesis of novel spiro[benzo[4,5]thiazolo[3,2-a]chromeno[2,3-d] pyrimidine-14,3′-indoline]-1,2′,13(2H)-triones via three component reaction [J].
Jannati, Saeideh ;
Esmaeili, Abbas Ali .
TETRAHEDRON, 2018, 74 (24) :2967-2972
[37]   Synthesis of some new 3-oxo-2-[(Z)-1-phenylmethylidene]-5H-[1,3]thiazolo[3,2-a]- and N-acetylated pyrimidines [J].
Mobinikhaledi, A. ;
Foroughifar, N. ;
Safari, J. Alipour ;
Mosleh, T. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (10) :2329-2335
[38]   Convenient one-pot access to novel densely functionalized pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidines via three component reaction [J].
Maryam Akhavan ;
Abbas Ali Esmaeili ;
Mahdieh Zangouei ;
Joel T. Mague .
Research on Chemical Intermediates, 2017, 43 :4683-4696
[39]   Ethyl 2-(benzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3, 2-a]pyrimidine-6-carboxylate analogues as a new scaffold for protein kinase casein kinase 2 inhibitor [J].
Jin, Cheng-Hao ;
Jun, Kyu-Yeon ;
Lee, Eunjung ;
Kim, Seongrak ;
Kwon, Youngjoo ;
Kim, Kunhong ;
Na, Younghwa .
BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (17) :4553-4565
[40]   Three-component reaction for synthesis of functionalized spiro[indoline-3,4′-pyrano[3,2-h]quinolines] [J].
Shi, Rong-Guo ;
Yan, Chao-Guo .
CHINESE CHEMICAL LETTERS, 2016, 27 (04) :575-578