A non-catalytic approach to the synthesis of 5,6-dihydrobenzo[h]quinolines |
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Authors: | Ramendra Pratap |
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Institution: | Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow 226 001, India |
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Abstract: | A concise synthesis of highly functionalized 5,6-dihydrobenzoh]quinoline-3-carbonitriles is delineated through base induced ring transformation of 4-sec-amino-2-oxo-5,6-dihydro-2H-benzoh]chromene-3-carbonitriles with S-methylisothiourea sulfate and 1-carboxamidinepyrazole hydrochloride, separately, in DMF. Under analogous reaction conditions the ring transformation of 4-sec-amino-2-oxo-5,6-dihydro-2H-benzoh]chromene-3-carbonitriles by formamidine acetate provided 4-sec-amino-benzoh]quinoline-3-carbonitriles in moderate yields, while with benzamidine hydrochloride, the reaction followed the same mechanism to yield 2-phenyl-4-sec-amino-5,6-dihydrobenzoh]quinoline-3-carbonitriles. |
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Keywords: | Benzo[h]quinoline 2-Oxo-5 6-dihydro-2H-benzo[h]chromene Ring transformation |
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