One‐pot synthesis of novel 2′‐deoxyuridine derivatives containing α‐aminophosphonate moieties

A series of α‐aminophosphonate derivatives of 2′‐deoxyuridine ( 8a–k ) have been prepared from 5′‐O‐tert‐butyldimethylsilyl‐3′‐amino‐2′, 3′‐dideoxyuridine in good yields. The structures of all the products were confirmed by ¹H NMR, ³¹P NMR, ³¹C NMR, and IR spectroscopy, and mass spectrometry and elemental analyses. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:230–235, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20288     

One‐pot synthesis of tetrahydroindeno[1,2‐b]pyrrolo‐3‐carboxylates derivatives

Tetrahydroindeno [1,2‐b]pyrrole‐3‐carboxylate were synthesized in a one‐pot procedure by the reaction of 1,3‐dicarbonyl and activated carbonyl compounds such as benzyl or ninhydrin in ethanol/water in the presence of ammonium acetate. J. Heterocyclic Chem., (2011).     

One‐pot synthesis of pyrido[2,3‐d]pyrimidines via efficient three‐component reaction in aqueous media

A short and facile synthesis of pyrido[2,3‐d]pyrimidine derivatives was accomplished in good yields via the three‐component reaction of aldehydes, alkyl nitriles and aminopyrimidines in water in the presence of triethylbenzylammonium chloride (TEBAC). The structures of these compounds were characterized by elemental analysis, IR and ¹H NMR spectra and further confirmed by single crystal X‐ray diffraction analysis.     

Tandem One‐pot Synthesis of Polysubstituted 1,3‐Thiazine Derivatives

A tandem one‐pot synthesis of polysubstituted 1,3‐thiazines has been developed by reacting with cyanoacetamide and isothiocyanate derivatives to give rise to 2‐cyano‐3‐mercaptoacrylamides, which are trapped in situ by various aldehydes or diversely substituted ketones through intermolecular cyclization, providing polysubstituted 1,3‐thiazine derivatives in short reaction times with good to excellent yields. The salient features of this novel protocol are operational simplicity, accessing the desired products from the readily available starting materials and easy of product isolation and may find wide spread applications in medicinal chemistry.     

The reaction of (N‐isocyanimino) triphenylphosphorane with (E)‐3‐aryl‐2‐ propenoic acid derivatives: One‐pot synthesis of 2‐[(E)‐2‐aryl‐1‐ethenyl]‐1,3,4‐oxadiazoles via intramolecular aza‐Wittig reaction

The reaction of (E)‐3‐aryl‐2‐propenoic acid derivatives with (N‐isocyanimino) triphenylphosphorane proceeds smoothly at room temperature to afford the corresponding 2‐[(E)‐2‐aryl‐1‐ethenyl]‐1,3,4‐oxadiazole via an intramolecular aza‐Wittig reaction in good yields under neutral conditions. The structures of the products were deduced from their IR, ¹H NMR, and ¹³C NMR spectra and mass spectrometry. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:612–616, 2011; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.20701     

Green chemistry approach to the synthesis of 2‐amino‐4‐aryl‐6‐ferrocenyl‐pyridine derivatives by a one‐pot reaction in aqueous medium

A clean and facile green chemistry method for the synthesis of a series of 2‐amino‐4‐aryl‐6‐ferrocenylpyridine derivatives was afforded. The products were synthesized via the one‐pot reaction of aromatic aldehyde, malononitrile or ethyl cyanoacetate, acetylferrocene and ammonium acetate in aqueous medium under microwave irradiation and conventional heating conditions without catalyst. This method had several advantages such as higher yield, lower cost, reduced environmental impact, and convenient procedure.     

One‐pot three‐component synthesis of 2‐substituted 4‐aminoquinazolines

A facile and rapid synthesis of the title compounds via one‐pot reaction of 2‐aminobenzonitrile, orthoesters and ammonium acetate under solvent‐free and microwave condition is described.     

One‐pot synthesis of new 3‐substituted coumarins by tandem reactions

The synthesis of new 3‐substituted coumarins appended to imidazolium, pyridinium, 3‐dimethylamino pyridinium, 3‐chloro pyridinium and 3‐bromo pyridinium salts is reported. These salts were prepared by tandem reactions, followed by quantitative anionic metathesis. The structure of these new 3‐substituted coumarins was established by NMR (¹H, ¹³C) and high‐resolution mass spectrometry.     

A One‐pot,Four‐component Protocol for the Synthesis of 2‐Aroylimino‐3‐aryl‐4‐methyl‐5‐acetyl‐1,3‐thiazolines

A concise and efficient route for the synthesis of new 2‐aroylimino‐3‐aryl‐4‐methyl‐5‐acetyl‐1,3‐thiazolines in good to excellent yields is described. This involves the one‐pot, four‐component reaction of suitable aroyl chlorides, potassium thiocyanate, anilines, and 3‐chloropentane‐2,4‐dione in the presence of N‐methylimidazole.     

One‐pot three‐component synthesis of novel 2‐(3‐nitro‐phenyl)‐quinazoline‐4‐carboxylic acid derivatives

A simple and easy synthesis of 2‐(3‐nitro‐phenyl)‐quinazoline‐4‐carboxylic acid ( 3 ) has been successfully developed through a one‐pot three‐component condensation reaction of (2‐amino‐phenyl)‐oxo‐acetic acid sodium salt ( 1 ) obtained from the hydrolysis of isatin with ammonium acetate and 3‐nitrobenzaldehyde. Some novel quinazoline‐ester derivatives 4‐7 were then obtained by the reaction between the new compound 3 and various alcohols. Then, quinazoline‐amide derivatives 10‐14 were synthesized from the reaction of various amines and 2‐(3‐nitro‐phenyl)‐quinazoline‐4‐carbonyl chloride ( 8 ), obtained by the reaction of compound 3 with SOCl₂. Finally, some novel quinazoline‐azo derivatives 17‐19 were synthesized by the coupling reaction between β‐dicarbonyl compounds and the novel amino‐quinazoline derivative compound 15 , obtained by reduction of nitro‐quinazoline derivative compound 11 . Thus, a new series of quinazoline‐4‐carboxylic acid, ester, amide, and azo derivatives was synthesized and fully characterized by ¹H NMR, ¹³C NMR, IR, and mass spectrometry analysis.     

One‐pot synthesis of novel N‐cyclopropyldecahydroacridine‐1,8‐dione derivatives under microwave irradiation

A series of new N‐cyclopropyldecahydroacridine‐1,8‐dione derivatives were synthesized by one‐pot reaction of aromatic aldehyde, dimedone (or 1,3‐cyclohexanedione) and cyclopropanamine in solution of glycol and water under microwave irradiation with excellent yields (78‐94%) and short reaction time (5‐10 min).     

Synthesis and fungicidal activity of 1,3‐thiazoline derivatives bearing nitrophenyl group on the 2‐position

Ortho‐, meta‐, or para‐nitro benzoic acid were refluxed with excess SOCl₂ to give acyl chloride, which condensed with β‐amino alcohol in the presence of Et₃N in dichloromethane to afford β‐hydroxyamide; finally, sulphonation and cyclization were simultaneously conducted to afford 1,3‐thiazoline derivatives. Fungicidal activity of these new thiazolines against eight agrocultural fungi were evaluated, and two of this type of compounds displayed good fungicidal activity comparable or superior to commercial fungicide chlorothalonil against two fungi at a concentration of 50 mg/L. J. Heterocyclic Chem., (2011).     

One‐pot synthesis of novel substituted pyrrolo[2,3‐d]pyrimidines using dry media

A convenient solvent‐free one‐pot synthesis of 1,3,5,7‐tetraaryl‐1,3,4,7‐tetrahydro‐2‐thio‐xopyrrolo[2,3‐d]pyrimidin‐4‐one derivatives using supported reagents under microwave irradiation is described. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:617–621, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20355     

One‐pot synthesis of pyridine derivatives via diels‐alder reactions of 2,4‐dimethyl‐5‐methoxyoxazole

A novel series of pyridine derivatives with anticipated biological activity have been synthesized via Diels‐Alder reactions of 2,4‐dimethyl‐5‐methoxyoxazole with different types of dienophiles. The regioselectivity of the cycloaddition was inverted from methylacrylate to tert‐butylacrylate. The structural elucidation of the new compounds was carried on the basis of spectral and X‐ray analyses. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:49–55, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20064     

A novel synthesis of 5‐aryl‐3‐phenylpyrazole from 2‐aryl‐3‐benzoyl‐1,1‐cyclopropanedicarbonitrile and hydrazine

A new process for synthesis of 5‐aryl‐3‐phenylpyrazole is achieved. The regioselective ring‐opening reaction of 2‐aryl‐3‐benzoyl‐1,1‐cyclopropanedicarbonitrile with hydrazine plays a crucial role in the described process.