An Approach to the Diastereoselective Synthesis of Cyclohexane-1,3-dicarboxamide Derivatives via a Pseudo Five-Component ­Reaction Based on Diketene

Abstract

A one-pot pseudo five-component reaction for the synthesis of 2-aryl-4-hydroxy-4-methyl-6-oxo-N 1,N 3-dialkylcyclohexane-1,3-dicarboxamide derivatives involving different primary amines, various aromatic aldehydes, and diketene in the presence of triethylamine with high yields is achieved.

Pyrazole‐promoted synthesis of pyrrolo[3,4‐c] quinoline-1,3‐diones in a novel diketene-based reaction

“…We considered the utilization of diketene as starting material and reagent because it is extensively used for the generation for a diverse range of different heterocycles. For this purpose, in continuation of our successive attempts towards the synthesis of heterocycles by multicomponent strategies, ( Rezvanian et al, 2018a ; Talaei et al, 2018 ; Rezvanian et al, 2020a ; Rezvanian et al, 2020b ), especially using diketene reactions ( Alizadeh et al, 2012 ; Rezvanian, 2015 ; Rezvanian, 2016 ; Rezvanian et al, 2017 ; Rezvanian et al, 2018b ; Rezvanian et al, 2019 ; Rezvanian et al, 2020c ; Rezvanian et al, 2020d ; Rezvanian et al, 2020e ; Rezvanian et al, 2021a ; Rezvanian et al, 2021b ), we herein explain an efficient approach to synthesize pyrrolo[3,4-c]quinoline-1,3-diones 7 from the reaction of isatin, diketene, and primary amines based on the unique reactivity of pyrazole as a promoter in high yields ( Scheme 3 ).…”

Diastereoselective Synthesis of 3,4-Dihydropyran-3-carboxamides with in Vitro Anti-inflammatory Activity

“…Considering the above points and our continued interest in the one-pot synthesis of heterocyclic compounds − wherein iodine is used as a Lewis acid catalyst, we designed a five-component Hantzsch-type reaction (Figure ) to construct a novel molecule bearing a 2-amino-3,4-dihydropyran-3-carboxamide core. As a useful building block, ,,− diketene was applied as one of the starting materials to form carboxamides directly.…”

Application of the Asymmetric Pictet–Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds

“…We are particularly interested in heterocyclic chemistry [ 45 , 46 , 47 , 48 , 49 , 50 , 51 ] and heterocyclic compounds exhibiting comparatively acceptable biological properties [ 51 , 52 , 53 ]. Recently, we have underscored the applications of several name reactions and stereoselective synthesis in the total synthesis of biologically active naturally occurring compounds [ 54 , 55 , 56 , 57 , 58 , 59 ]. In this report, we try to underline the most recent and current applications of another old but significant name reaction, PSR as a vital step in the total synthesis of biologically active natural products, specially, alkaloids.…”