Cycloaddition of a furan analogue of o-quinodimethane with quinones and their bromo derivatives

Autor:	Mouaffak Al Harin, Houda Fillion, Félix Pautet, Bernard Fenet, Monique Domard
Rok vydání:	1995
Předmět:	chemistry.chemical_compound Diene chemistry Furan Sodium iodide Organic Chemistry Drug Discovery Structural isomer Regioselectivity Biochemistry HOMO/LUMO Medicinal chemistry Cycloaddition
Zdroj:	Tetrahedron. 51:9595-9602
ISSN:	0040-4020
DOI:	10.1016/0040-4020(95)00534-f
Popis:	Dimethyl-4,5-bis(bromomethylene)furan-2,3-dioate 2 , generated “in situ” from the tetrabromo compound 1 and sodium iodide, was condensed with unsymmetrical quinones 7c-e , 10 and the 2-or 3-bromo naphthoquinones 8 or 9 . Starting from the latter, the cycloadditions were found more regioselective than from the non brominated quinones. Assignment of the regioisomers was made by 2D 1 H- 13 C HMQC and HMBC techniques performed on 12d, 11e and 12e . Calculations of HOMO and LUMO energies and the orbital coefficients by the semiempirical AM1 method indicate that 2 can be characterized as a rather neutral non polarised diene.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::920c48f87f1ee9ecf7f38603c2db26e7 https://doi.org/10.1016/0040-4020(95)00534-f Zobrazit plný text záznamu Full Text from ScienceDirect