Design, synthesis and biological activities of novel 1,2,3-thiadiazole derivatives containing oxime ether

Dong, Wen‐Kui; Yao, Hong-wei; Li, Zhengming; Zhao, Wei‐Guang

doi:10.3184/030823408x303998

Cited by 7 publications

References 11 publications

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The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Krapcho

Ciganek

2013

Organic Reactions

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The Krapcho reaction involves esters with α‐electron‐withdrawing substituents such as malonates, β‐keto esters, and α‐cyano esters, which undergo dealkoxycarbonylation on being heated in polar aprotic solvents (such as DMSO, DMF, or HMPT) in the presence of water, or in polar aprotic solvents with water in the presence of added salts (such as NaCN, NaCl, LiCl, LiI, or MgCl 2 ). This procedure avoids the use of strongly aqueous acidic and alkaline conditions and tolerates many functional and protecting groups. The chapter presents the mechanistic aspects of this procedure, which include reaction parameters such as solvents, salts, other additives, and the use of microwave irradiation. The diastereoselectivity of protonation of the enolate intermediate leading to the dealkoxycarbonylated products is discussed. Trapping of the intermediate enolate by electrophiles other than a proton is illustrated. Potential side reactions and same‐pot subsequent reactions of substrates are discussed along with functional‐group compatibility for halogens and nitrogen, oxygen, sulfur, selenium, and carbon functional groups. Several examples of applications of this methodology for the synthesis of natural products along with experimental conditions and procedures are presented. Closely related methods are discussed in the Comparison with Other Methods section. The tables, which consist of 371 pages, are grouped according to substrate structure. Selective entries for other methods (excluding classical aqueous acidic or basic methods) are included in the tabular survey for comparative purposes.

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The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Krapcho

Ciganek

2013

Organic Reactions

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ChemInform Abstract: Design, Synthesis and Biological Activities of Novel 1,2,3‐Thiadiazole Derivatives Containing Oxime Ether.

Dong

Yao

et al. 2008

ChemInform

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Design, synthesis and inhibitory activity against human dihydroorotate dehydrogenase ( h DHODH) of 1,3-benzoazole derivatives bearing amide units

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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Design, synthesis and biological activities of novel 1,2,3-thiadiazole derivatives containing oxime ether

Cited by 7 publications

References 11 publications

The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

ChemInform Abstract: Design, Synthesis and Biological Activities of Novel 1,2,3‐Thiadiazole Derivatives Containing Oxime Ether.

Design, synthesis and inhibitory activity against human dihydroorotate dehydrogenase ( h DHODH) of 1,3-benzoazole derivatives bearing amide units

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