Domino reaction of arylglyoxals with pyrazol-5-amines: Selective access to pyrazolo-fused 1,7-naphthyridines, 1,3-diazocanes, and pyrroles

Bo Jiang, Wei Fan, Mu Yan Sun, Qin Ye, Shu Liang Wang, Shu Jiang Tu, Guigen Li

Research output: Contribution to journalArticle

49 Scopus citations

Abstract

New multicomponent domino reactions of arylglyoxals with pyrazol-5-amines have been established, providing selective access to unprecedented pyrazolo-fused 1,7-naphthyridines, 1,3-diazocanes, and pyrroles (up to 52 examples). The unreported dipyrazolo-fused 1,7-naphthyridines were regioselectively synthesized through a special double [3 + 2 + 1] heteroannulation accompanied by direct C-C formation between two electrophilic sites of arylglyoxals. The unusual [3 + 3 + 1 + 1] cyclization resulted in 20 examples of novel dipyrazolo-fused 1,3-diazocanes, whereas pyrrolo[2,3-c] pyrazoles were obtained in good yields by varying arylglyoxals 1 and pyrazol-5-amines 2 in the ratio 1:2. Mechanisms of formation of these three new types of heterocycles are also proposed.

Original languageEnglish
Pages (from-to)5258-5268
Number of pages11
JournalJournal of Organic Chemistry
Volume79
Issue number11
DOIs
StatePublished - Jun 6 2014

Fingerprint Dive into the research topics of 'Domino reaction of arylglyoxals with pyrazol-5-amines: Selective access to pyrazolo-fused 1,7-naphthyridines, 1,3-diazocanes, and pyrroles'. Together they form a unique fingerprint.

Cite this