Curtius Rearrangement and Wolff Homologation of Functionalized Peroxides.

Dussault, Patrick H.; Xu, Chunping

doi:10.1002/chin.200503081

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Methods For the Synthesis Of Carbamates1

Wolff Rearrangement1

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2015

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Cited by 2 publications

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“…This method is widely employed in the transformation of carboxylic acids into carbamates and ureas. Acyl azides are usually prepared from carboxylic acid derivatives such as acyl chlorides, , mixed anhydrides, , and hydrazides. , Subsequent isocyanate intermediates can be trapped by a variety of nucleophiles to provide the carbamate derivatives. The acid chloride method is not suitable for acid-sensitive functionalities.…”

Section: Methods For the Synthesis Of Carbamatesmentioning

confidence: 99%

Organic Carbamates in Drug Design and Medicinal Chemistry

2015

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The carbamate group is a key structural motif in many approved drugs and prodrugs. There is an increasing use of carbamates in medicinal chemistry and many carbamate derivatives are specifically designed to make drug-target interactions through their carbamate moiety. In this review, we present properties and stabilities of carbamates, reagents and chemical methodologies for the synthesis of carbamates, and recent application of carbamates in drug design and medicinal chemistry.

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Section: Methods For the Synthesis Of Carbamatesmentioning

confidence: 99%

Organic Carbamates in Drug Design and Medicinal Chemistry

2015

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“…Dussault and Xu found that diazoketones containing peroxy substituents undergo Wolff rearrangement to afford homologated peroxyalkanoates to an extent that was reaction condition dependent (Scheme 46). 107 Thus, reaction of diazoketones 18 and 19 with silver benzoate and triethylamine in methanol furnished homologated peroxy products in excellent yield. These conditions were much less successful when applied to substrates 20 and 21.…”

Section: Wolff Rearrangementmentioning

confidence: 99%