A convenient synthesis of 3-cyano-4-imino-2-methylthio-4H-pyrimido [2,1-b] [1,3] benzothiazole and its reactions with selected nucleophiles

被引：26
|
作者：
Pingle, Mayura S.
Vartale, Sambhaji P.
Bhosale, Vijay N.
Kuberkar, Sharad V. [1 ]
机构：
[1] Post Grad Res Ctr, Dept Chem, Nanded 431602, India
[2] Govt Coll Pharm, Dept Pharmaceut Chem, Aurangabad 431005, Maharashtra, India
来源：
ARKIVOC | 2006年
关键词：
2-amino-6H-methylbenzothiazole; bis(methylthio)methylenemalononitrile; 3-cyano-4-imino-2-methylthio-4H-pyrimido [2,1b] [1,3] benzothiazole;
D O I：
10.3998/ark.5550190.0007.a22
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Amino benzothiazole (1) and 2-amino-6-methyl benzothiazole (4) in N, N'-dimethyl formamide (DMF) and anhydrous potassium carbonate reacted with bis(methylthio) methylene malononitrile (2) to afford 3-cyano-4-imino-2-methylthio-4H-pyrimido [2,1-b] [1,3] benzothiazole (3) and 3-cyano-4-imino-2-methylthio-8-methyl-4H-pyrimido [2,1-b] [1,3] benzothiazole (5), respectively. The latter were further reacted with selected N-, O- and C- nucleophiles such as aryl and hetaryl amines, substituted phenols and compounds with an active methylene group.
引用
收藏
页码：190 / 198
页数：9
相关论文
共 50 条
  • [31] SYNTHESIS AND PHARMACOLOGICAL PROPERTIES OF THIENO[2',3'-4,5]PYRIMIDO[2,1-B][1,3,4]THIADIAZINE DERIVATIVES
    SANTAGATI, A
    MODICA, M
    SANTAGATI, M
    CUTULI, V
    AMORE, D
    CARUSO, A
    FARMACO, 1995, 50 (09): : 605 - 609
  • [32] Transition metal complexes of ligand 4-imino-3-[(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)diazenyl]-4H pyrimido[2,1-b][1,3]benzothiazol-2-ol containing benzothiazole moiety: Synthesis, spectroscopic characterization and biological evaluation
    Rangappa, Maliyappa M.
    Keshavayya, Jathi
    Krishna, Panchangam Murali
    Rajesh, K.
    INORGANIC CHEMISTRY COMMUNICATIONS, 2021, 127
  • [33] 12-IMINO-12H-BENZIMIDAZO[2,1-B][1,3]BENZOTHIAZINE
    RODIER, N
    METTEY, Y
    VIERFOND, JM
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 : 1058 - 1060
  • [34] One-pot, catalyst-free synthesis of novel spiro[indole-3,4′-pyrano[2′,3′:4,5]pyrimido [2,1-b][1,3]benzothiazole] derivatives
    Zangouei, Mahdieh
    Esmaeili, Abbas Ali
    JOURNAL OF CHEMICAL RESEARCH, 2020, 44 (11-12) : 646 - 652
  • [35] Diversity Oriented Synthesis of 4H-Pyrimido[2,1-b]benzothiazole Derivatives via Biginellis Reaction: A Review
    Gandhi, Divyani
    Kalal, Priyanka
    Prajapat, Prakash
    Agarwal, Dinesh Kumar
    Agarwal, Shikha
    COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2018, 21 (04) : 236 - 253
  • [36] Synthesis and evaluation of antimicrobial activity of 4H-pyrimido[2,1-b] benzothiazole, pyrazole and benzylidene derivatives of curcumin
    Sahu, Pramod K.
    Sahu, Praveen K.
    Gupta, S. K.
    Thavaselvam, D.
    Agarwal, D. D.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 54 : 366 - 378
  • [37] 3-Bromo-7-methoxy-2-phenylimidazo[2,1-b][1,3] benzothiazole
    Bunev, Alexander S.
    Sukhonosova, Elena V.
    Syrazhetdinova, Dinara R.
    Statsyuk, Vladimir E.
    Ostapenko, Gennady I.
    Khrustalev, Victor N.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O531 - +
  • [38] SYNTHESIS OF SOME 4H-PYRIMIDO[2,1-B]BENZOTHIAZOL-4-ONES
    ALAIMO, RJ
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1973, 10 (05) : 769 - 772
  • [39] Synthesis of New Derivatives of 4-Methyl-3-nitro-6H-pyrimido[2,1-b]quinazoline
    Banihashemi, S. M.
    Hassani, H.
    Lari, J.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (02) : 322 - 326
  • [40] A facile green synthesis and in vitro antimicrobial activity 4H-pyrimido[2,1-b][1,3]benzothiazole derivatives using aluminum trichloride under solvent free conditions
    Sahu, Pramod K.
    Sahu, Praveen K.
    Lal, Jaggi
    Thavaselvam, D.
    Agarwal, D. D.
    MEDICINAL CHEMISTRY RESEARCH, 2012, 21 (11) : 3826 - 3834
12345