Synthesis of fused thiazolo[3,2-a]pyrimidinones: N-aryl-2chloroacetamides as doubly electrophilic building blocks

被引:7
|
作者
Banothu, Janardhan [1 ]
Basavoju, Srinivas [1 ]
Bavantula, Rajitha [1 ]
Crooks, Peter A. [2 ]
机构
[1] Natl Inst Technol, Dept Chem, Warangal 506004, Andhra Pradesh, India
[2] Univ Arkansas Med Sci, Coll Pharm, Dept Pharmaceut Sci, Little Rock, AR 72205 USA
关键词
Thiazolo[3,2-alpyrimidinones; 2-Chloro-N-phenylacetamide N-(Benzo[d]thiazol-2-y1)-2-; chloroacetamide; Single crystal X-ray analysis; DERIVATIVES; THIAZOLOPYRIMIDINES; PYRIMIDINE;
D O I
10.1016/j.tetlet.2013.11.001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Chloro-N-phenylacetamide and N-(benzo[d]thiazol-2-y1)-2-chloroacetamide are doubly electrophilic building blocks for the formation of ring annulated thiazolo[3,2-a]pyrimidinone products. This synthetic route involves formation of the title compound in acceptable product yields by the elimination of the by-product, aniline/2-aminobenzothiazole. Analytical and spectral studies, as well as single crystal X-ray data on the representative compound 6c confirmed the structure of all the reaction products. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:224 / 226
页数:3
相关论文
共 50 条
  • [21] SYNTHESIS OF THIAZOLO[3,2-A]THIENO[2,3-D]-PYRIMIDINES
    GAKHAR, HK
    BHARDWAJ, S
    BAVEJA, P
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1977, 15 (04): : 347 - 348
  • [22] New synthesis of 2,3-dihydro-thiazolo[3,2-a]benzimidazoles
    F. A. Khaliullin
    E. E. Klen
    Chemistry of Heterocyclic Compounds, 2009, 45 : 876 - 877
  • [23] Studies on thiazolopyridines.: Part 2.: Synthesis and antimicrobial activity of novel thiazolo[3,2-a] pyridine and thiazolo[3,2-a][1,8] naphthyridine derivatives having two different aryl moieties
    Ali, GAME
    Khalil, A
    Ahmed, AHA
    El-Gaby, MSA
    ACTA CHIMICA SLOVENICA, 2002, 49 (02) : 365 - 376
  • [24] 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):
  • [25] Novel Synthesis of Pyrano[2,3-d]Thiazole, Thiazolo[3,2-a]Pyridine, and Pyrazolo [3′,4′:4,5] Thiazolo[3,2-a]Pyridine Derivatives
    El-Hag Ali, G. A. M.
    Abd El-Rahman, M. T.
    Helal, M. H. M.
    El-Gaby, M. S. A.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (12) : 3023 - 3036
  • [26] Microwave assisted synthesis and AChE inhibition studies of novel thiazolo and thiadiazolo [3,2-a]pyrimidinone fused dihydrofuran compounds
    Mehmet Yilmaz
    Aslı Ustalar Inal
    Sait Sari
    Medicinal Chemistry Research, 2023, 32 : 957 - 974
  • [27] Direct Synthesis of Trichloro-thiazolo[3,2-a]pyrimidine and Thiazolo[2,3-b]quinazoline Derivatives
    Darehkordi, Ali
    Fazli-Zafarani, Seyed Mahdi
    Kamali, Mansoureh
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (04) : 2287 - 2296
  • [28] Microwave assisted synthesis and AChE inhibition studies of novel thiazolo and thiadiazolo [3,2-a]pyrimidinone fused dihydrofuran compounds
    Yilmaz, Mehmet
    Inal, Asli Ustalar
    Sari, Sait
    MEDICINAL CHEMISTRY RESEARCH, 2023, 32 (05) : 957 - 974
  • [29] Synthesis and Structure of 6-Acetyl-2-Arylhydrazone Derivatives of Thiazolo[3,2-a]Pyrimidine
    Agarkov, Artem S.
    Mingazhetdinova, Dilyara O.
    Nefedova, Anna A.
    Ovsyannikov, Alexander S.
    Shiryaev, Andrey K.
    Litvinov, Igor A.
    Solovieva, Svetlana E.
    Antipin, Igor S.
    ORGANICS, 2023, 4 (03): : 438 - 446
  • [30] Synthesis, Chemical Properties, and Application of 2-Substituted Thiazolo[3,2-a]pyrimidine Derivatives
    Agarkov, A. S.
    Shiryaev, A. K.
    Solovieva, S. E.
    Antipin, I. S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (03) : 337 - 364