Oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson's reagent

被引：12

作者：

Lashmanova, Eugenia A. ^{[1
]}

Kirdyashkina, Anastasiya I. ^{[1
]}

Slepukhin, Pavel A. ^{[2
]}

Shiryaev, Andrey K. ^{[1
]}

机构：

[1] Samara State Tech Univ, 244 Molodogvardeyskaya St, Samara 443100, Russia

[2] I Ya Postovsky Inst Organ Synth, 20-22 Acad Skaya,S Kovalevskoi St, Ekaterinburg 620990, Russia

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 12期

关键词：

Thiazolopyrimidine; Dimethyl sulfoxide; Lawesson's reagent; Oxidation; Dimerization; BIOLOGICAL EVALUATION; THIOINDIGO; DERIVATIVES; PYRIMIDINES; NORBORNENE; ACID; DYES;

D O I：

10.1016/j.tetlet.2018.02.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,2'-Dimers with a central double bond were prepared by the oxidation of 5,6-disubstituted 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson's reagent at room temperature. The role of DMSO as an oxidizing reagent was confirmed by NMR spectroscopy. The E-configuration of the central C=C bond for the two diastereomers of compound 8m was proven by single crystal X-ray data. The dimeric thiazolopyrimidines were orange or red colored and absorption bands at 283-330 and 459-476 nm were observed in the UV spectra. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：1099 / 1103

页数：5

共 50 条

[31] A Synthesis of Dihydrofuran-3(2H)-ones
Tata, Rama Rao
Harmata, Michael
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (13) : 6839 - 6845
[32] METHODOLOGY TO ACCESS THIAZO[3′,2′:2,3[PYRIDO[4,5-d]-THIAZOLO[3,2-a]PYRIMIDINONES
Wang, Dao-Lin
Wang, Dong
Li, Qiao-Min
Qian, Jian-Hua
HETEROCYCLES, 2016, 92 (12) : 2244 - 2251
[33] Regioselective Synthesis of 5H-Thiazolo[3,2-a]pyrimidin-5-ones from Morita-Baylis-Hillman Adduct Acetates under Solvent-Free and Base-Free Conditions
Zhong, Weihui
Guo, Baoming
Lin, Fuliang
Liu, Yongliang
Su, Weike
SYNTHESIS-STUTTGART, 2009, (10): : 1615 - 1622
[34] Synthesis and characterisation of some novel fused thiazolo[3,2-a] pyrimidinones and pyrimido[2,1-b][1,3]thiazinones
Abbas, Ikhlass M.
Gomha, Sobhi M.
Elaasser, Mahmoud M.
Mabrouk, Bazada K. A.
JOURNAL OF CHEMICAL RESEARCH, 2015, (12) : 719 - 723
[35] Synthesis and Characterization via Molecular Quantum Parameters of 2H-Thiazolo[3,2-a]pyrimidine-3,5,7(6H)-trione
Hamama, Wafaa S.
Ismail, Mohamed A.
Soliman, Mamdouh S.
Shaaban, Saad
Zoorob, Hanafi H.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (03) : 494 - 498
[36] Synthesis and antitumor activity of certain new thiazolo[2,3-b]quinazoline and thiazolo[3,2-a]pyrimidine analogs
Hassan, Ghada S.
MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (01) : 388 - 401
[37] Synthesis of Functionalized Pyridazin-3(2H)-ones via Bromine-Magnesium Exchange on Bromopyridazin-3(2H)-ones
Ryabtsova, Oxana
Verhelst, Tom
Baeten, Mattijs
Velde, Christophe M. L. Vande
Maes, Bert U. W.
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) : 9440 - 9445
[38] Synthesis of novel thiazolo[3,2-a]chromeno[4,3-d]pyrimidine-6(7H)-ones by bioactive Fe3O4@gly@thiophen@Cu(NO3)2 as reusable magnetic nanocatalyst
Hosseinzadegan, Sara
Hazeri, Nourallah
Maghsoodlou, Malek Taher
APPLIED ORGANOMETALLIC CHEMISTRY, 2020, 34 (09)
[39] Access to Seleno-Functionalized Thiazolo[3,2-a]Pyrimidinones and Pyrimido[2,1-b][1,3]Thiazinones via Selenocyclization of 2-Alkenylthiopyrimidinones and Their Fused Analogs
Vaskevych, Alla
Shishkina, Svitlana
Dekhtyar, Maryna
Smolii, Oleg
Vovk, Mykhailo
CHEMISTRYSELECT, 2024, 9 (36):
[40] A new reaction of P4S10 and Lawesson's reagent;: a new method for the synthesis of dithieno[3,2-b;2′,3′-d]thiophenes
Ertas, E
Ozturk, T
TETRAHEDRON LETTERS, 2004, 45 (17) : 3405 - 3407

← 1 2 3 4 5 →