Synthesis of pyrrolo[2,3-g]-and pyrrolo[3,2-f]quinolines from 5-amino-2,3-dimethyl-and 1,2,3-trimethylindoles with 4,4,4-trifluoroacetoacetic ester |
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| Authors: | S A Yamaskhin G A Romanova E A Oreshkina N V Zhukova |
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| Institution: | (1) Mordovian N. P. Ogarev State University, Saransk, 430000 Mordovia, Russia;(2) M. E. Evsev’ev State Teaching Institute, Saransk, 430007 Mordovia, Russia |
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| Abstract: | It has been shown that the condensation reaction of 5-amino-2,3-dimethyl-and 1,2,3-trimethylindoles with 4,4,4-trifluoroacetoacetic
ester occurs either via the trifluoromethylcarbonyl or the ester group depending upon the conditions under which it is carried
out. Under thermal conditions (refluxing in diphenyl) the enaminocrotonates formed are readily converted to pyrrolo3,2-f]quinolines
and the amides cyclize in trifluoroacetic acid at 78°C to give pyrrolo2,3-g]quinolines.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 86–96, January, 2006. |
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| Keywords: | 5-amino-2 3-dimethylindole 5-amino-1 2 3-trimethylindole pyrrolo[2 3-g]quinoline pyrrolo[3 2-f]quinoline ethyl 4 4 4-trifluoroacetoacetate |
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