Heterocyclizations of Functionalized Heterocumulenes with C,N- and C,O-Dinucleophiles: II.* Reaction of 1-Chloro- and 1,1-Dichloroalkyl Isocyanates and 1-Chloroalkylidenecarbamates with 2-Bensothiazolylacetonitrile, 2-Benzothiazolylacetates,and Bis(2-benzothiazolyl)methane |
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Authors: | Vovk M V Lebed' P S Sukach V A Kornilov M Yu |
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Institution: | (1) Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, Kiev, 02094, Ukraine;(2) Taras Shevchenko Kiev National University, Kiev, Ukraine |
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Abstract: | 1-Chloroalkyl isocyanates react with 2-R-methylbenzothiazoles R = CN, C(O)OAlk, 2-benzothiazolyl] in the presence of triethylamine to give 4-R-2,3-dihydro-1H-pyrimido6,1-b]1,3]benzothiazol-1-ones. The same reaction at elevated temperature in the absence of a base yields isomeric 4-R-2,3-dihydro-1H-pyrimido6,1-b]1,3]benzothiazol-3-ones. 4-R-1H-Pyrimido6,1-b]1,3]benzothiazol-1-ones are formed in the reaction of 1,1-dichloroalkyl isocyanates or methyl 1-chloroalkylidenecarbamates with 2-benzothiazolylacetonitrile or bis(2-benzothiazolyl)methane. |
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