Three-component one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in 2,2,2-trifluoroethanol

Abstract

Trifluoroethanol (TFE) is found to be an efficient and recyclable medium in promoting onepot, three-component coupling reactions of isatoic anhydride, aldehyde and ammonium acetate or primary amine to afford the corresponding 2,3-dihydroquinazolin-4(1H)-one derivatives in high yields. The solvent (TFE) can be readily separated from reaction products and recovered in excellent purity for direct reuse.ß 2012 Published by Elsevier Masson SAS on behalf of Acade ´mie des sciences.

Fluorinated alcohols: A magic medium for the synthesis of heterocyclic compounds

“…Our group reported recently an efficient synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives via one-pot condensation of isatoic anhydride, aldehydes and NH 4 OAc in TFE without using any catalyst or additives (Scheme 11) [83]. One of the major advantages of this protocol is the isolation and purification of the products.…”

2,3-Dihydroquinazolin-4(1H)-one as a privileged scaffold in drug design

“…The absence of catalyst again afforded 74-97% yield but in longer reaction times (1-6 h). [193][194][195][196][197] Urea or thiourea was used in the multi-component synthesis of DHQs as the ammonia surrogate under catalyst-free conditions. 198 A very efficient and fast synthesis of DHQs was attempted under both catalyst-and solvent-free conditions (>90% yield, in 3-10 min).…”

A Simple and Convenient Synthesis of 2, 3-dihydroquinazolin-4(1H)-one Derivatives using MgFe2O4@SiO2-SO3H Catalyst

“…In the past, a number of research efforts have been made to synthesis of quinazolinone and its derivatives through one pot three component synthesis involving several catalysts such as; DBSA [7], Trifluoroethanol (TFE) [8], AcOH [9], Thiamine hydrochloride (VB1) [10], Aluminium methanesulfonate [11], A strong acidic cationexchange resin [12], TiO2 nanoparticles [13], CuO nanoparticles [14], Tartaric acid-sodium dodecyl sulfate (SDS) [15], MCM-41-SO3H [16], Silica-supported Preyssler nanoparticles [17], Nano-In2O3 [18], Cu-CNTs [19], Titanium Silicon Oxide Nanopowder [20].Using βcyclodextrin-SO3H [21], Zirconium (IV) chloride [22], FeCl3/Al2O3 [23] catalysts two components synthesis of 2,3-dihydroquinazolin-4(1H)-ones was carried out using 2-aminobenzamide and substituted aldehyde/ketone. However, most of the synthetic protocols reported so far have several drawbacks such as drastic reaction conditions, longer reaction times, low yields, tedious work-up procedures and the use of hazardous solvents.…”