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

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 11期

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

页码：1351 / 1353

页数：3

共 50 条

[21] Synthesis and Structure of 7-Hydroxy-5-Oxo-2,3-Dihydro-5H-[1,3]Thiazolo[3,2-a]-Pyrimidine-6-Carboxylic Acid Ethyl Ester
Ukrainets, I. V.
Grinevich, L. A.
Alekseeva, T. V.
PHARMACEUTICAL CHEMISTRY JOURNAL, 2017, 51 (01) : 56 - 59
[22] Convenient one-pot access to novel densely functionalized pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a] pyrimidines via three component reaction
Akhavan, Maryam
Esmaeili, Abbas Ali
Zangouei, Mahdieh
Mague, Joel T.
RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (08) : 4683 - 4696
[23] A novel one-pot isocyanide-based three-component reaction: synthesis of highly functionalized imidazo-chromen-4-ones
Keshipour, Sajjad
Shaabani, Ahmad
Shojaei, Salman
Nosrati, Hamed
Ng, Seik Weng
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2015, 12 (09) : 1655 - 1663
[24] SYNTHESIS AND CHARACTERIZATION OF FUNCTIONALIZED DIHYDROPYRIMIDINONES VIA ONE-POT ISOCYANIDE-BASED THREE-COMPONENT REACTION OF N-FORMYL UREA AND DIALKYL ACETYLENEDICARBOXYLATES
Naderi, Ainaz
Mohtat, Bita
BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2017, 31 (02) : 345 - 350
[25] Efficient one-pot three-component synthesis of novel spiro(indoline-3,7′-thiazolo[3,2-a]pyrimidine) derivatives
Jamshidi, Zahra
Esmaeili, Abbas Ali
Mague, Joel T.
JOURNAL OF CHEMICAL RESEARCH, 2016, (08) : 471 - 474
[26] Construction of Spiro[indoline-3,2′-pyrrolo[2,1-a]Isoquinoline] and Spiro[indoline-3,2′-pyrrolo[1,2-a]Quinoline] via Isocyanide-Based Three-Component Reaction
Liu, Dong-Mei
He, Yu-Wei
Han, Ying
Sun, Jing
Yan, Chao-Guo
CHEMISTRYSELECT, 2025, 10 (04):
[27] Synthesis of Highly Substituted 4H-Pyrido[1,2-a]pyrimidines via a One-Pot Three-Component Condensation Reaction
Yang, Kai
Xiang, Jinbao
Bao, Guochen
Dang, Qun
Bai, Xu
ACS COMBINATORIAL SCIENCE, 2013, 15 (09) : 519 - 524
[28] Synthesis of Highly Functionalized Bis(4H-chromene) and 4H-Benzo[g]chromene Derivatives via an Isocyanide-Based Pseudo-Five-Component Reaction
Shaabani, Ahmad
Ghadari, Rahim
Sarvary, Afshin
Rezayan, Ali Hossein
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) : 4372 - 4374
[29] Novel isocyanide-based three-component reaction: a facile synthesis of substituted 1H-chromeno[2,3-d]pyrimidine-5-carboxamides
Soleimani, Ebrahim
Ghorbani, Somayeh
Ghasempour, Hamid Reza
TETRAHEDRON, 2013, 69 (39) : 8511 - 8515
[30] When Serendipity Knocks on the Door: Synthesis and Physicochemical Characterization of 7-Chloro-2,3-dihydro-5H-thiazolo[3,2-α]pyrimidin-5-one
Carmona-Vargas, Christian C.
Ellena, Javier
D'Vries, Richard F.
Chaur, Manuel N.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2019, 30 (07) : 1475 - 1482

← 1 2 3 4 5 →