Use of convertible isocyanides for the synthesis of benazepril hydrochloride

Borase, Bhushan B; Godbole, Himanshu M.; Singh, Girij Pal; Upadhyay, Pritesh R.; Trivedi, Anurag; Bhat, Varadaraj G; Shenoy, Gautham G.

doi:10.1007/s12039-021-01892-8

Cited by 1 publication

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“…At the same time, the use of so-called convertible isocyanides [ 27 – 36 ] in Ugi-4CR makes it possible to obtain carboxylic acids or esters after hydrolysis of the secondary amide group in the Ugi products ( Scheme 2 ) [ 27 – 29 31 – 32 34 – 36 ]. Ugi bisamides modified in this way may be subsequently used as acid components in tandem combinations of various multicomponent processes such as Ugi and Ugi, azido-Ugi and Ugi, Ugi and Passerini, Groebke–Blackburn–Bienaymé and Ugi, etc.…”

Section: Introductionmentioning

confidence: 99%

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

Tsygankov,

Vereshchak,

Savluk

et al. 2024

Beilstein J. Org. Chem.

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By one-pot four- and three-component Ugi reactions involving convertible isocyanides and unexplored pyrrole-containing β-chlorovinylaldehyde, a small library of 20 bisamides with unusual behavior in post-Ugi transformations was prepared and characterized. Surprisingly, a well-documented approach to obtain peptide-containing carboxylic acids through acid hydrolysis of the convertible isocyanide moiety in the Ugi bisamides proceeded in an unexpected manner in our case, leading to the formation of derivatives of amides of heterylidenepyruvic acid. An optimized synthetic protocol for this transformation was elaborated and a plausible sequence involving the elimination of the 2-chloroacetamide moiety and the conversion of the β-chlorovinyl fragment into a vinyl one is provided.

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