One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles

Abstract

A novel four-component reaction in one pot as an atom- and step-economic process was developed to synthesize diastereoselectively spirooxindolepyrrolothiazoles through sequential N,S-acetalation of aldehydes with cysteine and decarboxylative [3 + 2] cycloaddition with olefinic oxindoles. High synthetic efficiency, operational simplification and reaction process economy using EtOH as solvent, and only releasing CO2 and H2O as side products confer this approach favorable in green chemistry metrics analysis.

Regioselective Pd-Catalyzed Suzuki–Miyaura Borylation Reaction for the Dimerization Product of 6-Bromoimidazo[1,2-a]pyridine-2-carboxylate: Mechanistic Pathway, Cytotoxic and Tubercular Studies

“…11,12 One of these frameworks, imidazopyridine, is an important class of nitrogen-containing heterocycle that exhibits a wide range of biological activities such as antipyretic, analgesic, antimicrobial, antituberculosis, antifungal, anti-inflammatory, antitumor, antiviral, antibacterial, antiprotozoal, hypnoselective and anxioselective activities. 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 Furthermore, there are several drugs such as zolpidem (used in the treatment of insomnia), alpidem (as an anxiolytic agent), olprinone (for the treatment of acute heart failure), zolimidine (used for the treatment of peptic ulcer), necopidem and saripidem (both works as anxiolytic agents) available on the market that contain an imidazo[1,2- a ]pyridine moiety and serve as prominent drug candidates in current medicinal therapy. 29 30 31 On the other hand, aromatic dimers are ubiquitous reagents in organic synthesis, they play a significant role in pharmaceutical and chemical industries, and their use in the development of new drugs 32 such as maglonol, honokiol, pinoresinol, and bis-eugenol 33 34 35 (Figure 1 ) has been shown to have greater efficacy than the monomeric structure.…”