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Synthesis of bicyclic pyrazinones via addition of heterocyclic amines to a nitro-alkene

โœ Scribed by Margaret A. Brimble; Andrew D. Johnston


Book ID
104203089
Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
726 KB
Volume
50
Category
Article
ISSN
0040-4020

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โœฆ Synopsis


Michael addition of beterocyclic amines (6). (lo), ( 13) and ( 17) to nilro-olefm (3) followed by feductionkyclization of the ~&XI group of the adduct provides a convenient synthesis of the bicyclic pytazinones 0%. ( 12). ( 16). ( 19) and ( 20) which are found in several natmal pfoducts.


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Grignard reagents add to ketonirrones in a nonpolar solvent to afford N,N-dialkylhydroxylamines in good yieids and with liiule compeling proton Paqfer. ## Deoxygenalion of the crude hydroxylatrSnes with carbon disulfide then compleres an eficient general synthetic route to hindered set-alkyl-lert-a