Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions
نویسندگان
چکیده
Herein we describe a versatile approach for the synthesis of acylhydrazino-peptomers, a new class of peptidomimetics. The key idea in this approach is based on a simple route using a one-pot hydrazino-Ugi four-component reaction followed by a hydrazinolysis or hydrolysis reaction and subsequent hydrazino-Ugi reaction or classical Ugi reaction for the construction of acyclic acylhydrazino-peptomers. The consecutive multicomponent reactions produced a variety of acylhydrazino-peptomers in moderate to excellent yields (47-90%). These compounds are multifunctional intermediates that can be further functionalized to obtain new peptidomimetics with potential biological activity.
منابع مشابه
Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles
Isocyanide-based multicomponent reactions (IMCRs) allow the construction of relatively complex molecules through a one-pot synthesis. The combination of IMCRs in a consecutive or sequential fashion further extends the complexity of the molecules obtained. Herein, we report the efficient application of this approach to the synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles. Our str...
متن کاملA Novel Strategy of Ugi-4CR/Huisgen 1,3-Dipolar Synthesis of 1H-1,2,3-Triazole-Modified Peptidoimetics
In this protocol, we report a novel approach for the synthesis of a new class of heterocyclic 1H-1,2,3-triazole-modified peptidomimetic compounds. The process consists of an Ugi four-component condensation reaction of amines, an isocyanide, an aldehyde and acids followed by a Huisgen 1,3-dipolar cycloaddition reaction with an azide group in the presence of a catalytic amount of CuSO4</...
متن کاملAsymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives
An efficient Ugi three-component reaction of a preformed chiral ketimine derived from isatin with various isonitrile and acid components has been developed. The reactions proceeded smoothly and in a stereocontrolled manner with regard to the new center of the Ugi products due to the stereoinduction of the amine chiral residue. A wide variety of novel chiral 3,3-disubstituted 3-aminooxindoles we...
متن کاملN-Hydroxyimide Ugi Reaction toward α-Hydrazino Amides
The Ugi four-component reaction (U-4CR) with N-hydroxyimides as a novel carboxylic acid isostere has been reported. This reaction provides straightforward access to α-hydrazino amides. A broad range of aldehydes, amines, isocyanides and N-hydroxyimides were employed to give products in moderate to high yields. This reaction displays N-N bond formation by cyclic imide migration in the Ugi reacti...
متن کاملA novel intramolecular Ugi reaction with 7-azabicyclo[2.2.1]heptane derivatives followed by post-condensation acylations: a new entry to azanorbornyl peptidomimetics.
beta-amino acids have been employed in the past as bifunctional building blocks in intramolecular Ugi multicomponent reactions to yield beta-lactam derivatives. By using 7-azabicyclo[2.2.1]heptane-2-carboxylic acid, a different outcome has been observed and rationalised. The final compounds are polyfunctionalised azabicyclic peptidomimetics, and further elaboration can be achieved exploiting an...
متن کامل