Synthesis of 3-substituted 1,2,4-triazolo (3,4-b) benzothiazoles

被引:0
作者
Kapratwar, SB
Baheti, KG
Kuberkar, SV [1 ]
机构
[1] Yeshwant Mahavidyalaya, Dept Chem, Nanded 631605, India
[2] MGM, Coll Engn, Dept Chem, Nanded 431605, India
[3] Nanded Pharm Coll, Dept Pharmaceut Chem, Nanded 431605, India
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中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Hydrazino 1,2,4-triazolo (3,4-b) benzothiazole 1 on heating with methyl chloroformate, acetic anhydride and benzoyl chloride separately afforded 3-(N-carbomethoxy) hydrazino 2, 3-(1,2-diacetyl) hydrazino 5 and 3-(N-benzoyl) hydrazino-1,2,4-triazolo (3,4-b) benzothiazole 7 respectively. Compound 1 on treatment with acrylonitrile in the presence of pyridine yielded 3-propane nitrile derivative 8 which on refluxing with dil hydrochloric acid afforded 3-(pyrazol-5-one-1-yl)-1,2,4-triazolo (3,4-b) benzothiazole 9. N-[3-amino-1,2,4-triazolo (3,4-b) benzothiazole] phthalimide 10 was obtained by heating 1 with phthalic anhydride, 1-[3'-(1,2,4) triazolo (3,4-b) benzothiazolyl]3,5-dialkyl/diaryl-1,2,4-1H-triazoles 11a,b,c were prepared by condensing 1 with alkyl and aryl nitriles. Reaction of I with ethyl acetoacetate and acetyl acetone afforded 1-[3'-(1,2,4)-triazolo (3,4-b) benzothiazolyl]-3-ethoxy-5-methyl pyrazole 12 and 1-[3'-(1,2,4)triazolo (3,4-b) benzothiazolyl]-3,5-dimethyl pyrazole 13 respectively. But condensation of 1 with diethyl oxalate resulted in the formation of altogether different compound, 3-aminoformyl-1,2,4-triazolo (3,4-b) benzothiazole 15. All newly synthesized compounds were characterized on the basis of elemental and spectral analysis.
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页码:241 / 244
页数:4
相关论文
共 4 条
  • [1] HOFFMANN U, 1972, CHEM ZNTR, P279
  • [2] Kuberkar SV, 1996, INDIAN J CHEM B, V35, P842
  • [3] KUBERKAR SV, 1991, INDIAN J CHEM B, V30, P78
  • [4] RING CONTRACTION OF 1,2,4-TRIAZIN-3-ONES TO IMIDAZOLIN-2-ONES AND 1,2,3-TRIAZOLES
    REES, CW
    SALE, AA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (06): : 545 - 550