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The Curtius Rearrangement: Applications in Modern Drug Discovery and Medicinal Chemistry
Author(s) -
Ghosh Arun K.,
Brindisi Margherita,
Sarkar Anindya
Publication year - 2018
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201800518
Subject(s) - curtius rearrangement , isocyanate , chemistry , amine gas treating , drug discovery , combinatorial chemistry , organic chemistry , biochemistry , polyurethane
The Curtius rearrangement is the thermal decomposition of an acyl azide derived from carboxylic acid to produce an isocyanate as the initial product. The isocyanate can undergo further reactions to provide amines and their derivatives. Due to its tolerance for a large variety of functional groups and complete retention of stereochemistry during rearrangement, the Curtius rearrangement has been used in the synthesis of a wide variety of medicinal agents with amines and amine‐derived functional groups such as ureas and urethanes. The current review outlines various applications of the Curtius rearrangement in drug discovery and medicinal chemistry. In particular, the review highlights some widely used rearrangement methods, syntheses of some key agents for popular drug targets and FDA‐approved drugs. In addition, the review highlights applications of the Curtius rearrangement in continuous‐flow protocols for the scale‐up of active pharmaceutical ingredients.