ChemInform Abstract: tert‐Butyl Hydroperoxide and Tetrabutylammonium Iodide‐Promoted Free Radical Cyclization of α‐Imino‐N‐arylamides and α‐Azido‐N‐arylamides.

Li, Dianjun; Su, Hailin; Yu, Wei

doi:10.1002/chin.201551105

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“…When reactions were conducted under an argon atmosphere, in addition to 675, quinoxalin-2-ones 676 were obtained in 28−68% yields, through intramolecular orthoattacking cyclization of iminyl radical 677 or 1,2-migration of the iminyl moiety (678) to form radical 680, followed by oxidation and subsequent deprotonation (Scheme 172, a). 317 conditions, giving corresponding adducts 684 in 66−85% yields, with 70/30−92/8 dr. Reactions proceeded by alkyl radical generation via photolysis of Mn 2 (CO) 10 in the presence of alkyl iodides, followed by addition to imine moiety (685) and then H atom abstraction from solvent molecule (Scheme 173).…”

Section: Chemical Reviewsmentioning

confidence: 99%

α-Imino Esters in Organic Synthesis: Recent Advances

2017

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α-Imino esters are useful precursors for the synthesis of a variety of types of natural and unnatural α-amino acid derivatives, with a wide range of biological activities. Due to the adjacent ester group, α-imino esters are more reactive relative to other types of imines and undergo different kinds of reactions, including organometallics addition, metal catalyzed vinylation and alkynylation, aza-Henry, aza-Morita-Baylis-Hillman, imino-ene, Mannich-type, and cycloaddition reactions, as well as hydrogenation and reduction. This review discusses the mechanism, scope, and applications of the reactions of α-imino esters and related compounds in organic synthesis, covering the literature from the last 12 years.

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Section: Chemical Reviewsmentioning

confidence: 99%