A general and convenient procedure for the synthesis of azinones is presented. Cyclopropylmethanol is readily introduced onto various azines where it functions as both a protecting group and surrogate for hydroxyl. After acidic deprotection, under mild reaction conditions, the corresponding azinones are formed and isolated in excellent yields. >20 examples are included along with a discussion of reaction optimization, scope, and mechanism.
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Preparation of Azinones from (Cyclopropylmethoxy)azine Ethers.
J Org Chem
May 2023
Development & Medical, Pfizer Worldwide Research, Groton, Connecticut 06340, United States.
A general and convenient procedure for the synthesis of azinones is presented. Cyclopropylmethanol is readily introduced onto various azines where it functions as both a protecting group and surrogate for hydroxyl. After acidic deprotection, under mild reaction conditions, the corresponding azinones are formed and isolated in excellent yields.
View Article and Find Full Text PDFStraightforward entry to libraries of diversely substituted azinones by a consecutive aza-Michael/palladium-catalyzed functionalization strategy.
J Comb Chem
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Departamento de Química Organica, Facultad de Farmacia, Universidad de Santiago de Compostela, Spain.
A highly divergent, flexible, and conceptually simple sequence allowing the parallel solution-phase assembly of functionalized azinone libraries has been developed in a one-pot consecutive fashion. Structural decoration of in situ-generated heterocyclic aza-Michael adducts AB was accomplished by exploiting the diversity potential of Heck, Suzuki, Sonogashira, and Stille reactions.
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