RADICAL ANNULATIONS WITH NITRILES - NOVEL CASCADE REACTIONS OF CYANO-SUBSTITUTED ALKYL AND SULFANYL RADICALS WITH ISONITRILES

Citation
Cm. Camaggi et al., RADICAL ANNULATIONS WITH NITRILES - NOVEL CASCADE REACTIONS OF CYANO-SUBSTITUTED ALKYL AND SULFANYL RADICALS WITH ISONITRILES, Tetrahedron, 54(21), 1998, pp. 5587-5598
Citations number
44
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
54
Issue
21
Year of publication
1998
Pages
5587 - 5598
Database
ISI
SICI code
0040-4020(1998)54:21<5587:RAWN-N>2.0.ZU;2-C
Abstract
New radical annulation reactions are described involving addition of c yano-substituted alkyl and sulfanyl radicals to aromatic isonitriles. The tandem cyclisation of the resulting imidoyl radicals onto the cyan o group affords cyclopenta- and thienoquinoxalines, respectively. The intervention of the isonitriles in the aromatisation process of the cy ctohexadienyl radicals is discussed as well as the regiochemistry of t he cyclisation of the iminyl radicals obtained by addition of the imid oyls to the nitrile moiety. The hypothesis of an exclusive 6-membered ring closure onto the aromatic ring is also supported by the results o f semiempirical AM1 calculations. (C) 1998 Elsevier Science Ltd. All r ights reserved.