Hossein Mehrabi

SYNTHESIS OF 6-ACYLMETHYLPHENANTHRIDINE ENAMINONES

A series of 6-acylmethylphenanthridine derivatives were synthesized by reaction of aliphatic and aromatic esters with 6-methylphenanthridine in the presence of phenyllithium. Enaminone form of the obtained compounds was investigated by spectroscopic methods. The results revealed that the presence of aromatic rings on 3- and 4-position of 2-acylmethylquinolines (6-acylmethylphenanthridines) is the most important factor for the preference of the enaminone form b. It was found that the intramolecular hydrogen bonding is the only factor that can damage aromaticity of the phenanthridine moiety.

(E)-N′-Benzyl­idene-p-toluene­sulfono­hydrazide

In the title compound, C14H14N2O2S, a novel sulfonamide derivative, an intramolecular C—H⋯O hydrogen bond generates an S(5) ring motif. The molecule adopts a twisted E configuration around the C=N bond. An intermolecular N—H⋯O hydrogen bond generates an R 2 2(8) ring motif. The dihedral angle between the rings is 85.37 (9)°. The H atoms of the methyl group have rotational disorder with refined site occupancies of ca 0.63/0.37. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link neighbouring molecules into dimers which stack along the a axis with a centroid–centroid distance of 3.8856 (10) Å.

Study of Hydrazone-Hydrazoimine Tautomerism in α-Azo-6-ketomethylphenanthridines

AB Azo-coupling of a series of 6-ketomethylphenanthridines products was performed starting from 6- ketomethylphenanthridines and benzene diazonium chloride. The products were characterised using 1H, 13C and 15N NMR, IR, UV and MS spectroscopic methods. The hydrazoimine forms were the only tautomer present in chloroform solution. Two rotamers were detected in chloroform solutions of the compounds studied. Analysis of the NMR data shows that the ratio of rotamers depends on electron-donating and electron-withdrawing properties of the substituent present in the benzene ring.

A facile and efficient one-pot synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitrile derivatives in water

A one-pot three-component synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitriles from amines, carbon disulfide, and arylidenemalononitriles in H2O under reflux conditions, in good yields, is described.

A novel method for the synthesis of α-oximino-6-acylmethylphenanthridines under neutral conditions

A novel method is described for the synthesis of α-oximino-6-acylmethylphenanthridine derivatives (2a–g)B in good to excellent yields based on treatment of 6-acylmethylphenanthridines with isoamyl nitrite (IAN) in DMF without any added acid.

Efficient synthesis of novel heterocyclic dihydropyrimidine-2,4,5(3H)-trione and tetrahydro-2-thioxopyrimidine-4,5-dione derivatives

Novel heterocyclic dihydropyrimidine-2,4,5(3H)-triones and tetrahydro-2-thioxopyrimidine-4,5-diones were synthesized via three-component reaction between appropriate amines, phenyl isocyanate or phenyl isothiocyanate, and ethyl bromopyruvate in DMF under reflux conditions without using additional bases or catalysts. All the products were obtained in good yield by simple and efficient procedure. The structures of all the synthesized compounds were established from advanced spectroscopic data.

Efficient synthesis of symmetrical N,N'-alkylidene bisamides catalysed by acetyl chloride

Symmetrical bisamides were synthesised from aldehydes and amides in the presence of distilled acetyl chloride. The reaction is rapid, clean and gives the products in excellent yields.

An efficient synthesis of pentasubstituted pyrroles: one-pot four-component reaction of arylamine, acetylenedicarboxylate, arylglyoxal, and symmetrical 1,3-dicarbonyl compounds

An efficient and catalyst-free for the synthesis of dialkyl 5-(aryl)-4-(1,3-dicarbonyl)-1-(aryl)-1H-pyrrole-2,3-dicarboxylate via a novel one-pot four-component reaction of arylamine, acetylenedicarboxylate, arylglyoxal, and 1,3-dicarbonyl compounds in ethanol is reported. All the products were obtained in excellent yields and their structures were established from their spectroscopic data.

The reaction of active methylene compounds with carbon disulfide in the presence of arylidenemalononitriles: synthesis of 6-amino-2-(4,4-dimethyl/dihydro-2,6-dioxocyclohexylidene)-4-aryl-4H-1,3-dithiine-5-carbonitrile derivatives

ABSTRACT An efficient and simple method for the synthesis of novel ketene dithioacetals via a one-pot three-component reaction of 5,5-dimethylcyclohexan-1,3-dion or 1,3-cyclohexandion with carbon disulfide in the presence of arylidenemalononitriles is reported. The effects of different bases have been investigated and triethylamine can provide products in good to excellent yields at room temperature. The structures of all the synthesized compounds were established from advanced spectroscopic data. GRAPHICAL ABSTRACT

One-pot three-component condensation of β-naphthol with arylaldehydes and Meldrum's acid: synthesis of 1-aryl-1,2-dihydro-benzo[f]chromen-3-ones

An efficient and simple method for the synthesis of 1-aryl-1,2-dihydro-benzo[f]chromen-3-ones via a one-pot three-component reaction of β-naphthol, arylaldehydes and Meldrums acid with Et3N as a base in CH3CN under reflux is reported. All the products were obtained in good to excellent yields and their structures were established from their spectroscopic data.