Stereoselective syntheses of 20-epi cholanic acid derivatives from 16-dehydropregnenolone acetate

A stereoselective total synthesis of naturally occurring 20-epi cholanic acid derivatives has been realized, starting from readily available 16-dehydropregnenolone acetate. The key step of these syntheses involves an ionic hydrogenation of a C-20,22-ketene dithioacetal and deoxygenation of steroidal C-20 tert-alcohols, to set up the unnatural C(20R) configuration with 100% stereoselectivity. The unnatural C-22 aldehydes with C(20R) stereocenters thus obtained were elaborated to 20-epi cholanic acid derivatives. Two derivatives of 20-epi cholanic acid were synthesized and their structures have been confirmed by single crystal X-ray analysis. Catalytic hydrogenation of 16-dehydropregnenolone acetate and 16-dehydropregnenolone in ethanol affords C-5,C-16 tetrahydro products. Crystal structure analysis of one of these products revealed C-5α and C-17α configurations of the hydrogen atoms.     

[HDBU][HSO4]-catalyzed facile synthesis of new 1,2,3-triazole-tethered 2,3-dihydroquinazolin-4[1H]-one derivatives and their DPPH radical scavenging activity

Research on Chemical Intermediates - A simple and efficient protocol has been developed for the synthesis of new1,2,3-triazole-2,3-dihydroquinazolin-4[1H]-one (DHQ) conjugates(6a?j) via...     

Solvent-free sonochemical preparation of α-aminophosphonates catalyzed by 1-hexanesulphonic acid sodium salt

1-Hexanesulphonic acid sodium salt was found to be an efficient catalyst for the green synthesis of α-aminophosphonates by the coupling of aldehydes/ketone, an amine and triethyl phosphite under ultrasound irradiation at ambient temperature for appropriate time to furnish the desired product in good to excellent yield under solvent-free condition. This catalyst provides clean conversion; greater selectivity and easy workup make this protocol practical and economically attractive.     

Synthesis and biological activity of some fluorinated arylhydrazotriazoles

Potential biologically active derivatives of arylhydrazotriazole (3a–l) were prepared by the condensation reaction of diazonium salts using various aromatic amines (1a–l) and 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl) ethanones (2). The synthesized products were obtained in 75–85% yield. All the synthesized products were having good-excellent antifungal activity as compared with standard (Fluconazole and Ketoconazole) drugs.     

Synthesis and biological evaluation of novel triazole-biscoumarin conjugates as potential antitubercular and anti-oxidant agents

Research on Chemical Intermediates - The synthesis of a new series of triazole-biscoumarin conjugates by using a molecular hybridization approach is described. The newly synthesized compounds...     

Synthesis of new 4-(4,5-diphenyl-1h-imidazol- 2-yl)tetrazolo[1,5-<Emphasis Type="Italic">a</Emphasis>]quinolines from tetrazolo[1,5-<Emphasis Type="Italic">a</Emphasis>]quinolines

Some new 4,5-diphenyl-1H-imidazole derivatives were synthesized in good yields by treating various tetrazolo[1,5-a]quinolines with benzil and ammonium acetate in glacial acetic acid.     

Cellulose sulphuric acid as a biodegradable and reusable catalyst for the Knoevenagel condensation

A green, mild and efficient method for Knoevenagel condensation of 3-formylchromone/2-chlroquinoline-3-carbaldehyde with active methylene compounds such as Meldrum’s acid/ethyl cyanoacetate using biosupported cellulose sulphuric acid (CSA) in the solid-state by grinding under solvent-free condition has been developed. This method provides several advantages including environmental friendliness, shor t reaction times, high yields and a simple work-up procedure. Moreover, the CSA was successfully reused for four cycles without significant loss of activity.     

l-Hexanesulphonic acid sodium salt promoted the one-pot synthesis of amidoalkyl naphthols under microwave-irradiation

Amidoalkyl naphthols have been synthesized in high yields in the presence of 1-hexanesulphonic acid sodium salt as an inexpensive solid catalyst under solvent-free conditions and microwave-irradiation.This catalyst provides clean conversion;greater selectivity and easy workup make this protocol practical and economically attractive.     

Stereoselective syntheses of unnatural steroidal C(20R) aldehydes by ionic hydrogenation of C-20 tertiary alcohols

Syntheses of three unnatural steroidal C(20R) aldehydes have been realised from 16-dehydropregnenolone acetate. The salient feature of the synthesis is the ionic hydrogenation of C-20 tertiary alcohols leading to the formation of the C(20R) unnatural isomer with complete stereoselectivity. Oxidative hydrolysis of the dithiane moiety furnished the C(20R) aldehydes.