Synthesis of natural quinazolinones and some of their analogues through radical cascade reactions involving N-acylcyanamides

Two natural quinazolinones and two analogues can be prepared from the cascade cyclizations of alkyl-substituted N-acylcyanamide radicals, including 5-exo-dig or 6-exo-dig cyclizations onto the cyano group, followed by radical arylations of the resulting amidyl radicals. The fact that one can carry o...

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Bibliographic Details
Published in:	Tetrahedron Vol. 69; no. 36; pp. 7699 - 7705
Main Authors:	Larraufie, Marie-Hélène, Malacria, Max, Courillon, Christine, Ollivier, Cyril, Fensterbank, Louis, Lacôte, Emmanuel
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 09-09-2013 Elsevier
Subjects:	Aromatic compounds Cascades Chemical Sciences Cyanamides Cyano groups Organic chemistry Quinazolinones Radical reactions Radicals Synthesis Tetrahedrons Versatility Radical reactions Quinazolinones Cyanamides
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Summary:	Two natural quinazolinones and two analogues can be prepared from the cascade cyclizations of alkyl-substituted N-acylcyanamide radicals, including 5-exo-dig or 6-exo-dig cyclizations onto the cyano group, followed by radical arylations of the resulting amidyl radicals. The fact that one can carry out the cascades from alkyl radicals in addition to aryl, vinyl and aminyl ones, shows the versatility of the method to rapidly access nitrogen-containing polycyclic structures. [Display omitted]
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2013.05.058