Diels-Alder reactions of pyridine o-quinodimethane analogues generated from functionalised o-bis(chloromethyl)pyridines

Autor:	Georges J. Hoornaert, Steven L. Cappelle, Frans Compernolle, Peter R. Carly
Rok vydání:	1996
Předmět:	chemistry.chemical_classification Organic Chemistry Iodide Propargyl chloride Biochemistry Medicinal chemistry Cycloaddition Adduct chemistry.chemical_compound chemistry Drug Discovery Pyridine Diels alder Organic chemistry Isoquinoline Methyl acrylate
Zdroj:	Tetrahedron. 52:11889-11904
ISSN:	0040-4020
Popis:	The polyfunctional 2,3- and 3,4-o-bis(chloromethyl)pyridines 3, produced via cycloaddition of the oxazinones 2 with propargyl chloride and 1,4-dichloro-2-butyne, were used as precursors of various pyridine o-quinodimethane analogues. The 2,3- and 3,4-dimethylenepyridine systems were generated via reductive 1,4-elimination with iodide and trapped in situ with various dienophiles to form the tetrahydroquinoline and -isoquinoline type adducts. A regiospecific cycloaddition was observed for the 3,4-dimethylenepyridine system with electron-rich dienophiles, i.e. dihydrofuran and ethyl vinyl ether, in contrast to the reaction with methyl acrylate.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::40d37f6eff3417693d85f7951b1760d4 https://doi.org/10.1016/0040-4020(96)00680-1 Zobrazit plný text záznamu Full Text from ScienceDirect