In-situ generation of poly(quinolizine)s via catalyst-free polyannulations of activated diyne and pyridines

He, Beihai; Huang, Jiachang; Zhang, Jing; Wang, Dong; Sung, Herman H. Y.; Liu, Yajun; Qin, Anjun; Lam, Jacky W. Y.; Tang, Ben Zhong

doi:10.1007/s11426-021-1225-4

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2023

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“…In recent years, in situ generated Huisgen 1,4-dipoles were also widely employed to design highly efficient multicomponent and domino reactions [ 16 – 25 ]. Recently, much attention has been devoted to the development of new domino reactions containing reactive Huisgen 1,4-dipoles as key components for the assembly of many biologically important nitrogen-containing six-membered heterocyclic compounds [ 26 – 30 ].…”

Section: Introductionmentioning

confidence: 99%

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

Chen

Zheng

Han

et al. 2023

Beilstein J. Org. Chem.

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The three-component reaction of isoquinolines, dialkyl acetylenedicarboxylates, and 5,6-unsubstituted 1,4-dihydropyridines in acetonitrile at room temperature afforded functionalized isoquinolino[1,2-f][1,6]naphthyridines in good yields and with high diastereoselectivity. More importantly, the formal [2 + 2] cycloaddition reaction of dialkyl acetylenedicarboxylates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile gave unique 2-azabicyclo[4.2.0]octa-3,7-dienes as major products and 1,3a,4,6a-tetrahydrocyclopenta[b]pyrroles as minor products via further rearrangement.

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