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
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
  • [1] A Convenient One Pot Synthesis of 3-Cyano-9-methyl-2-methylthio-4-oxo-4H- pyrimido[2,1-b] pyrimido [4,5-b] Quinoline and its Reactions with Selected Nucleophiles
    Vartale, Sambhaji P.
    Bhosale, Vijay N.
    Khansole, Sandeep V.
    Katapalle, Ramdas N.
    LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (07) : 544 - 548
  • [2] Novel Synthesis and Biological Activity of 2-Substituted Derivatives of 3-Cyano-4-imino-2-methylthio-8-methoxy-4H-pyrimido[2,1-b][1,3]benzothiazole and 3-Amino-4-imino-8-methoxy-2H-pyrazolo[3′,4′:4,5]pyrimido[2,1-b][1,3]benzothiazole
    Badne, S. G.
    Swamy, D. K.
    Bhosale, V. N.
    Kuberkar, S. V.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (04) : 849 - 855
  • [3] Synthesis, characterization, and biological activities of 4-imino-3-arylazo-4H-pyrimido[2,1-b][1,3]benzothiazole-2-oles
    Selinay Erişkin
    Nesrin Şener
    Serkan Yavuz
    İzzet Şener
    Medicinal Chemistry Research, 2014, 23 : 3733 - 3743
  • [4] Synthesis, characterization, and biological activities of 4-imino-3-arylazo-4H-pyrimido[2,1-b][1,3]benzothiazole-2-oles
    Eriskin, Selinay
    Sener, Nesrin
    Yavuz, Serkan
    Sener, Izzet
    MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (08) : 3733 - 3743
  • [5] SYNTHESIS AND IN VITRO ANTICANCER ACTIVITY OF 8-CHLORO-3-CYANO-4-IMINO-2-METHYLTHIO-4H-PYRIMIDO [2, 1-B] [1, 3] BENZOTHIAZOLE AND ITS 2-SUBSTITUTED DERIVATIVES
    Labhsetwar, Leena B.
    Shendarkar, Giridhar R.
    Kuberkar, Sharad V.
    ASIAN JOURNAL OF PHARMACEUTICAL RESEARCH AND HEALTH CARE, 2010, 2 (03) : 273 - 278
  • [6] Synthesis and Biological Activity of 2-Amino-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylates
    Chaithanya, M. S.
    Vaidya, V. P.
    Nagendrappa, G.
    ASIAN JOURNAL OF CHEMISTRY, 2011, 23 (04) : 1618 - 1620
  • [7] Synthesis and biological activity of 4H-pyrimido [2,1-b] benzothiazole-8-substituted-2-thiomethyl-3-cyano-4-ones
    Baheti, KG
    Kuberkar, S
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 12 (04) : 343 - 346
  • [8] A convenient synthesis of 2,3-disubstituted derivatives of 4H-pyrimido[2,1-b]benzothiazole-4-one
    Baheti, KG
    Kapratwar, SB
    Kuberkar, SV
    SYNTHETIC COMMUNICATIONS, 2002, 32 (14) : 2237 - 2243
  • [9] PYRIMIDINES .3. THE SYNTHESIS OF OXAZOLO[2,3-B]PYRIMIDINONES, PYRIMIDO[2,1-B][1,3]OXAZINONES, AND PYRIMIDO[2,1-B][1,3]BENZOXAZINONES
    ABARCA, B
    SORIANO, C
    JONES, G
    JOURNAL OF CHEMICAL RESEARCH-S, 1987, (05): : 158 - 158
  • [10] Crystal structure of ethyl 4-(2-chlorophenyl)-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate
    Kumar, Balbir
    Kour, Manmeet
    Paul, Satya
    Kant, Rajni
    Gupta, Vivek K.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O669 - +