Guanidine and amidine mediated synthesis of bridgehead triazaphenalenes, pyrimidines and pyridines through domino reactions

Pratap, Ramendra ; Roy, Abhijeet Deb ; Kushwaha, Shom Prakash ; Goel, Atul ; Roy, Raja ; Ram, Vishnu Ji (2007) Guanidine and amidine mediated synthesis of bridgehead triazaphenalenes, pyrimidines and pyridines through domino reactions Tetrahedron Letters, 48 (33). pp. 5845-5849. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/j.tetlet.2007.06.073

Related URL: http://dx.doi.org/10.1016/j.tetlet.2007.06.073

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.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:2-Oxo-4-(piperidin-1-yl)-5,6-dihydro-2H-benzo[h]-chromene-3-carbonitriles; Oxaheteroaromatics; Ring transformation.
ID Code:117926
Deposited On:06 May 2021 09:13
Last Modified:06 May 2021 09:13

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