Guanidine and amidine mediated synthesis of bridgehead triazaphenalenes, pyrimidines and pyridines through domino reactions |
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Authors: | Ramendra Pratap Shom Prakash Kushwaha Raja Roy |
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Affiliation: | a Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow 226 001, India b Division of SAIF, Central Drug Research Institute, Lucknow 226 001, India |
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Abstract: | An efficient and concise synthesis of 8-amino-2,5-diaryl-1,9,9b-triazaphenalene-4-carbonitriles has been delineated through two successive base catalyzed heteroaromatic annulations of 6-aryl-4-(piperidin-1-yl)-2H-pyran-2-one-3-carbonitriles by guanidine hydrochloride in moderate yield. This reaction was further explored through the ring transformation of 4 with amidines 8 and 11 to afford (2,6-diarylpyrimidin-4-yl)acetonitriles and 6-aryl-4-(piperidine-1-yl)nicotinonitriles in excellent yields. |
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Keywords: | 2-Oxo-4-(piperidin-1-yl)-5,6-dihydro-2H-benzo[h]-chromene-3-carbonitriles Oxaheteroaromatics Ring transformation |
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