Microwave-assisted multicomponent synthesis of antiproliferative 2,4-dimethoxy-tetrahydropyrimido[4,5-b]quinolin-6(7H)-ones

Abstract

Herein, we demonstrate a simple, rapid and green synthesis of 2,4-dimethoxy-THPQs under microwave irradiation and their antiproliferative activity, in silico ADMET and drug-likeness studies were carried out.

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

“…Patel and his group demonstrate the microwave-assisted MCR for the synthesis of pyrimido [4,5-b]quinoline derivatives 561 by using aromatic aldehydes 1, 6-amino-2,4-dimethoxypyrimidine and dimedone in acetic acid medium (Scheme 107). [126] Initially, Knoevenagel condensation between aromatic aldehyde and dimedone in presence of acetic acid formed Knoevenagel adduct 562 with the elimination of water. Next, 6amino-2,4-dimethoxy aniline reacts with Knoevenagel adduct 562 formed an imine derivative 563 which undergoes intramolecular ring-closing through CÀ N bond formation followed by the elimination of another water molecule give the desired pyrimido [4,5-b]quinoline derivatives 561.…”

“…up to 20 : 1 (syn : anti)) and tetrahydro‐8 H ‐pyrazolo[4,3‐f]pyrimido[4,5‐b]quinoline‐8,10(9 H )‐diones 534 (Scheme 102). [121] …”

“…Patel and his group demonstrate the microwave‐assisted MCR for the synthesis of pyrimido[4,5‐ b ]quinoline derivatives 561 by using aromatic aldehydes 1 , 6‐amino‐2,4‐dimethoxypyrimidine and dimedone in acetic acid medium (Scheme 107). [126] …”

Regiospecific synthesis of novel spiro‐pyrimidobarbiturates with promising antibacterial activities

“…In recent years, different synthetic strategies for the synthesis of spiro ‐barbiturates have been developed such as; substituted pyrimidine‐5‐spiro‐chromanes were prepared via hydride transfer reaction of 5‐(2‐alkoxyarylidene) barbituric acids A [7]; spiro ‐cyclopropyl and spiro dihydrofuryl barbiturates B were obtained by chemoselective one pot‐cascade reaction of arylidene barbituric acids with acetylacetone in the presence of N ‐bromosuccinimide under basic condition [8]; preparation of diastereoselectivity of spiro ‐pyrazolo[4,3‐ f ]quinoline]‐8,5′‐pyrimidines C (20: 1) ( syn : anti ) was achieved via multicomponent reaction of 5‐aminoindazole, benzaldehyde with N , N ‐dimethylbarbituric acid using betaine‐based DEMs [9]; spiro ‐furo[2,3‐ d ]pyrimidine‐6,5′‐pyrimidines D were obtained via multicomponent reaction of barbituric acids, aliphatic/aromatic aldehydes with cyanogen bromide in the presence of TEA [10]; spiro ‐pyrazolobarbiturates E via 1,3‐dipolar cycloaddition reaction of arylidene barbiturates with CH and CBr nitrilimines with reverse regioselectivity at different reaction temperatures [11]; spiro ‐isoxazolobarbiturates F via 1,3‐dipolar cycloaddition reaction of arylidene barbiturates with dibromoformaldoxime in basic conditions [12]; spiro ‐barbiturate tetrahydrothiophene hybrids G via reaction of N , N ‐dimethylbarbituric acid with various aromatic aldehydes and 1,4‐dithiane‐2,5‐diol under catalyst‐free conditions [13]; and spiro ‐pyrimidobarbiturates H via multicomponent reaction of urea with aromatic aldehydes and/or barbituric acid using ZnCl 2 –GELA catalyst under aerobic conditions [14] (Figure 1).…”

An efficient, catalyst-free and aqueous ethanol-mediated synthesis of 5-((2-aminothiazol-5-yl)(phenyl)methyl)-6-hydroxypyrimidine-2,4(1H,3H)-dione derivatives and their antioxidant activity

“…Melting points were resolute using the open capillary tube method and were uncorrected. NMR spectra ( 1 H NMR &13 C NMR) were recorded on Bruker 500 MHz, JEOL 500 MHz, and JEOL 400 MHz NMR spectrometer using solvent peak as CDCl 3 /DMSO-d 6 solvent. LCMS analyses were performed on an MS-Agilent 6120 quadrupole spectrometer and HRMS was determined on Waters Micro mass Q-Tof Micro 4000 quadrupole spectrometer.…”