An efficient one-pot synthesis of pyrimido[2,1-b][1,3]thiazine derivatives by reaction of activated acetylenes, thiouracils, and isocyanides

被引:26
|
作者
Baharfar, Robabeh [1 ]
Baghbanian, Seyed Meysam [1 ]
Vahdat, Seyed Mohammad [2 ]
机构
[1] Univ Mazandaran, Dept Chem, Babol Sar, Iran
[2] Islamic Azad Univ, Ayatollah Amoli Branch, Dept Chem, Amol, Iran
关键词
Pyrimido[2,1-b][1,3]thiazines; Isocyanides; Activated acetylenes; Multicomponent reaction; PYRIMIDINE; ACIDS;
D O I
10.1016/j.tetlet.2011.09.008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactive 1:1 zwitterionic intermediate, formed by the addition of isocyanides to dialkyl acetylenedi-carboxylates, was trapped by thiouracils to yield a ketenimine intermediate, which cyclized and then rearranged to afford pyrimido[2,1-b][1,3]thiazines in good yields. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6018 / 6020
页数:3
相关论文
共 50 条
  • [41] POLYANILINE SULFATE SALT MEDIATED ONE-POT THREE-COMPONENT SYNTHESIS OF TRIHETEROCYCLIC 4H-PYRIMIDO[2,1-B]BENZOTHIAZOLE DERIVATIVES
    Reddy, K. R. Vijayapal
    Rao, T. V. D. Prasad
    HETEROCYCLIC LETTERS, 2019, 9 (01): : 35 - 39
  • [42] A one-pot regioselective synthesis of benzo[d]imidazo[2,1-b]thiazoles
    Zhang, Xinhai
    Jia, Jiong
    Ma, Chen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (39) : 7944 - 7948
  • [43] Synthesis of pyrimido[2,1-b][1,3]benzothiazoles and [1,3]benzothiazolo [3,2-a]quinazolines via one-pot three-component reactions from 2-aminobenzothiazole, arylglyoxals and 1,3-dicarbonyl compounds
    Alizadeh-Bami, Farzaneh
    Mehrabi, Hossein
    Ranjbar-Karimi, Reza
    ARKIVOC, 2019, : 228 - 238
  • [44] One-pot synthesis and fungicidal activities of derivatives of imidazo[2,1-b]-1,3,4-thiadiazol-5(6H)-one
    Sun, Yong
    Fu, Bo-Qiao
    Ding, Ming-Wu
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (06) : 1437 - 1443
  • [45] Elemental Sulfur-Promoted Tandem One-Pot Synthesis of Diverse 4H-Pyrimido[2,1-b]benzothiazoles
    Mathavan, Sivagami
    Yamajala, Rajesh B. R. D.
    CHEMISTRYSELECT, 2021, 6 (40): : 10735 - 10738
  • [46] Enzyme-catalysed one-pot synthesis of 4H-pyrimido[2,1-b] benzothiazoles and their application in subcellular imaging
    Yu, Yuan
    Zhang, Wei
    Gong, Qing-Tian
    Liu, Yan-Hong
    Yang, Zeng-Jie
    He, Wei-Xun
    Wang, Na
    Yu, Xiao-Qi
    JOURNAL OF BIOTECHNOLOGY, 2020, 324 : 91 - 98
  • [47] NAPHTHO(2,3-D)PYRIMIDO(2,1-B)(1,3)THIAZINES
    GAKHAR, HK
    GUPTA, R
    KUMAR, N
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1978, 55 (05) : 474 - 475
  • [48] Regioselectivity in the Reaction of 2-Aminobenzothiazoles and 2-Aminobenzimidazoles with Enaminonitriles and Enaminones: Synthesis of Functionally Substituted Pyrimido[2,1-b][1,3]benzothiazole and Pyrimido[1,2-a]benzimidazole Derivatives
    Alnajjar, Abdulaziz
    Abdelkhalik, Mervat Mohammed
    Riad, Hossam Mohammed
    Sayed, Samia Mohammed
    Sadek, Kamal Usef
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (12) : 2760 - 2765
  • [49] SYNTHESIS OF PYRIMIDO[2,1-B]BENZOXAZOLIUM, PYRIMIDO[2,1-B]BENZOTHIAZOLIUM AND PYRIMIDO[1,2-A]BENZIMIDAZOLIUM SALTS BY REACTION OF 3-ISOTHIOCYANATO-2-PROPENIMINIUM SALTS WITH O-FUNCTIONALIZED ANILINES
    RIEMER, B
    LIEBSCHER, J
    SYNTHESIS-STUTTGART, 1993, (01): : 75 - 76
  • [50] One-Pot Synthesis of 1H-Naphtho[2,1-b]pyran Derivatives under Solvent-Free Conditions
    Devi, Kshretrimayum Ameeta
    Chanu, L. Gellina
    Chanu, I. Harimala
    Singh, Okram Mukherjee
    LETTERS IN ORGANIC CHEMISTRY, 2014, 11 (10) : 743 - 747