The Curtius Rearrangement: Applications in Modern Drug Discovery and Medicinal Chemistry. [PDF]
ChemMedChem, 2018 AbstractThe 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
Ghosh AK, Brindisi M, Sarkar A.
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The Curtius rearrangement: mechanistic insight and recent applications in natural product syntheses. [PDF]
Org Biomol Chem, 2018 An extensive review on the Curtius reaction and its recent applications in the synthesis of bioactive natural products are reported.
Ghosh AK, Sarkar A, Brindisi M.
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Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement. [PDF]
J Am Chem Soc, 2017 The Curtius rearrangement is a classic, powerful method for converting carboxylic acids into protected amines, but its widespread use is impeded by safety issues (the need to handle azides).
Zhao W, Wurz RP, Peters JC, Fu GC.
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An efficient new method for the synthesis of 3-[18 F]fluoro-4-aminopyridine via Yamada-Curtius rearrangement. [PDF]
J Labelled Comp Radiopharm, 2018 4-Aminopyridine is a clinically approved drug to improve motor symptoms in multiple sclerosis. A fluorine-18-labeled derivative of this drug, 3-[18 F]fluoro-4-aminopyridine, is currently under investigation for positron emission tomography (PET) imaging ...
Basuli F +4 more
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Boc-protected 1-(3-oxocycloalkyl)ureas via a one-step Curtius rearrangement: mechanism and scope. [PDF]
Tetrahedron Lett, 2014 Treatment of carboxylic acids (I) with Et3N, DPPA, and tBuOH provides the title ureas as major products via Curtius rearrangement followed by an unexpected nucleophilic addition of the resulting tert-butyl carbamate to an in situ generated isocyanate ...
Sun X +5 more
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Pyridone annulation via tandem Curtius rearrangement/6π-electrocyclization: total synthesis of (-)-lyconadin C. [PDF]
Org Lett, 2013 A concise, enantioselective total synthesis of the Lycopodium alkaloid (-)-lyconadin C was achieved in 12 steps and high overall yield. Key features include construction of a luciduline congener through Mannich-type cyclization and a one-pot, tandem ...
Cheng X, Waters SP.
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Oxidative N−N Bond Formation Versus the Curtius Rearrangement
Chemistry – A European JournalAbstractThe oxidative formation of N−N bonds from primary amides has been recently reported and then retracted in the journal Nature Communications by Kathiravan, Nicholls, and co‐authors, utilizing a hypervalent iodane reagent. Unfortunately, the authors failed to recognize the Curtius reaction taking place under the described reaction conditions ...
Melissa Hohenadel +3 more
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Phys Chem Chem PhysThe Curtius and the Wolff rearrangement reactions are investigated in the gas phase by tandem mass spectrometry (MS) and infrared ion spectroscopy (IRIS), probing the nature and intrinsic reactivity of three acyl azides and of one α-diazo keto analyte ...
Harnying W +8 more
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N-Acylbenzotriazoles as Proficient Substrates for an Easy Access to Ureas, Acylureas, Carbamates, and Thiocarbamates via Curtius Rearrangement Using Diphenylphosphoryl Azide (DPPA) as Azide Donor [PDF]
Synthesis, 2021 A diverse range of ureas, N-acylureas, carbamates, and thiocarbamates has been synthesized in good to excellent yields by reacting N-acylbenzotriazoles individually with amines or amides or phenols or thiols in the presence of diphenylphosphoryl azide ...
Vinod K. Tiwari +4 more
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Stereospecificity of the Curtius rearrangement [PDF]
Canadian Journal of Chemistry, 1968 Jones and Mason claimed a number of years ago (1) that rearrangement of cis-olefinic acyl azides gave trans-olefinic isocyanates. However, several other workers have found that rearrangement of an acyl azide group attached to an optically active carbon gives configurationally identical products, a discovery which apparently conflicts with Jones and ...
Martin B. Hocking
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