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Relevant academic research and scientific papers

An Efficient One-pot Three-component Method for the Synthesis of 5-Amino-3-(2-oxo-2H-chromen-3-yl)-7-aryl-7H-thiazolo[3,2-a]pyridine-6,8-dicarbonitriles

A facile, convenient, and adequate method has been developed for the synthesis of novel 5-amino-3-(2-oxo-2H-chromen-3-yl)-7-aryl-7H-thiazolo[3,2-a]pyridine-6,8-dicarbonitriles (6) by employing 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)acetonitrile (3) as an important precursor. Initially, we have synthesized the target compounds in a stepwise manner and then approached a tandem method to examine the feasibility of one-pot method. Subsequently, one-pot three-component protocol has been established for the synthesis of title compounds by the reaction of 3 with benzaldehyde and malononitrile in refluxing ethanol engender a new six-membered thiazolo[3,2-a]?pyridine as a hybrid scaffold. Reaction conditions were optimized for this reaction and a broad substrate scope with various aryl and heteroaryl aldehydes make this protocol very practical, attractive, and worthy. Mechanistic aspects for the formation of these compounds were outlined comprehensively. Characterization of these newly synthesized compounds was achieved by means of IR, 1H NMR, 13C NMR, and HRMS.

An efficient one-pot four-component Gewald reaction: Synthesis of substituted 2-aminothiophenes with coumarin–thiazole scaffolds under environmentally benign conditions

An elegant and efficient method has been outlined for the synthesis of novel 5-amino-4-[4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl]-3-arylthiophene-2-carbonitriles employing a one-pot four-component reaction of various aldehydes, 2-[4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl]acetonitrile, malononitrile and molecular sulfur independently in the presence of L-proline as a catalyst, under green reaction conditions. In an alternative approach, initially, the Knoevenagel condensation of these various aldehydes has been carried out with active methylene compounds malononitrile or 2-[4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl]acetonitrile to obtain the corresponding condensed compounds. These compounds then further subjected to a one-pot three-component Gewald reaction with molecular sulfur using sodium bicarbonate as a simple and inexpensive catalyst to obtain the target compounds. The effect of solvent and catalyst on these reactions has been screened to obtain the optimal conditions. The advantages of this protocol are the use of mild reaction conditions at ambient temperature, environmental friendliness, good yields in faster reaction times, convenient operation procedures, and broad substrate scope.

Reactions with hydrazonoyl halides XXIV[1]: Synthesis of some new unsymmetrical azines and dihydro-1,3,4-thiadiazoles

Unsymmetrical azines were synthesized from reaction of C-coumarinoyl-N-arylformohydrazonoyl bromide with different alkyl carbodithioates. In addition, reactions of hydrazonoyl halides with thioanilide and methyl dithioates were studied. The structures of newly synthesized compounds were confirmed by elemental analyses, spectroscopic tools, and alternative syntheses whenever possible.

Ensembles of rings with a coumarin unit. 1. Synthesis of 3-(2-R-thiazol-4-yl)- and 3-(4-R-triazol-2-yl)coumarins

We have synthesized 3-(2-R-thiazol-4-yl)coumarins (R = H, CH3, CH2CN, Ar) by condensation of 3-(α-bromoacetyl)coumarins with thioamides. We obtained 3-(4-R-thiazol-2-yl)coumarins (R = H, Ar) by several methods. By reaction of 2-cyanomethyl-4-phenylthiazole with 2-hydroxybenzaldehydes, we synthesized 2-imino-3-(4-phenylthiazol-2-yl)coumarins, which were converted to the corresponding coumarins by acid hydrolysis. For 3-(2-R-thiazol-4-yl)coumarins (R = CH2CN), we carried out reactions with aromatic aldehydes. We propose alternative methods for synthesis of 2-[2-aryl(hetaryl)-1-cyanoethenyl]-4-(coumarin-3-yl)thiazoles. 1998 Plenum Publishing Corporation.

3-α-Bromacetyl-coumarines as Synthones for Heterocyclic Substituted Coumarines

3-α-Bromacetyl-coumarines 2 react easily and in high yields with thiourea and thioamide derivatives 3 and 5, resp., to 4-coumar-3'-yl-thiazoles 4 and 6, resp., as well as with N,N-disubstituted thioamides 11 and N,N,N',N'-tetraalkylthiourea 12 to 5-coumar-3'-yl-oxathioliumsalts 13 and 14, respectively.In a two-step reaction 2 can be transformed by reaction with aniline 17 to 4-coumar-3'-yl-imidazoles 21 and 5-coumar-3'-yl-oxazoliumsalts 22, resp., via aminoketone intermediates 18.