2-(Acylmethylmercapto)-3-amino- and 2-(acylmethylmercapto)-3-acetamidopyridines

The reaction of 2-mercapto-3-acetamido-5-(or 6-)chloropyridines with phenacyl bromide and substituted phenacyl bromides yielded 2-(phenacylmercapto)-3-acetamidopyridines, while the reaction of the former with -chloroacetoacetic ester yielded 2-(carbethoxyacyl-methylmercapto)-3-acetamidopyridlnes.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1391–1394, October, 1971.     

3-(2-Quinolyl)- and 3-(5-carbethoxyfuryl-2)coumarins

3-(2-Quinolyl)- and 3-(5-carbethoxyfuryl-2)coumarins were prepared by reaction of substituted salicylaldehydes and hetarylacetonitriles. Alkylation and acylation of 3-hetaryl-7-hydroxycoumarins were studied. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 432–434, September–October, 2005.     

Preparation of 2(3)-O-[2-(hydroxyamino)-2-oxoethyl]- and 2(3)-O-[3-(hydroxyamino)-3-oxopropyl]dextran

Hydroxame derivatives of carboxymethyl- and carboxyethyldextrans have been prepared and characterized by elemental analysis as well as by IR and UV spectroscopy. The effect of reaction conditions on the products yield has been studied.     

Synthesis and Crystal Structure of（E）-Ethyl 2-（5-（3-methyl-2-butenyloxy）-2-（3-（4-（3-methyl-2-butenyloxy）phenyl）acryloyl）phenoxy）acetate

The title compound,(E)-ethyl 2-(5-(3-methyl-2-butenyloxy)-2-(3-(4-(3-methyl-2-butenyloxy)phenyl) acryloyl) phenoxy)acetate(1),has been synthesized and characterized by FT-IR and 1H-NMR spectroscopy,ESI-MS,and X-ray single-crystal diffraction.FT-IR,1H-NMR and ESI-MS confirm the functional groups,particularly the ethyl groups in the ester moiety,of the compound.The single-crystal X-ray diffraction has revealed a monoclinic structure,space group P21/n with a = 14.6832(14),b = 7.7581(7),c = 23.075(2),β = 101.670(2)o,V = 2574.2(4) ?3,Z = 4,Dc = 1.235 g/cm,μ = 0.085 mm-1,and F(000) = 1024.The skeleton of chalcone in the molecular structure is coplanar.     

Preparation,molecular structures,and characteristic properties of (E)-1-(2-furyl)- and (E)-1-(2-thienyl)-2-(3-guaiazulenyl)ethylenes and (E)-1-(3-furyl)- and (E)-1-(3-thienyl)-2-(3-guaiazulenyl)ethylenes

Wittig reactions of 2-furaldehyde (20) [and thiophene-2-carbaldehyde (21)] with (3-guaiazulenylmethyl)triphenylphosphonium bromide (19) in ethanol containing NaOEt at 25 °C for 24 h under argon give (E)-1-(2-furyl)-2-(3-guaiazulenyl)ethylene (22E) and (E)-1-(2-thienyl)-2-(3-guaiazulenyl)ethylene (23E) in 53 and 36% yields. Similarly, Wittig reactions of 3-furaldehyde (29) [and thiophene-3-carbaldehyde (30)] with 19 under the same reaction conditions as for 20 and 21 afford (E)-1-(3-furyl)-2-(3-guaiazulenyl)ethylene (31E) and (E)-1-(3-thienyl)-2-(3-guaiazulenyl)ethylene (32E) in 32 and 46% yields. Molecular structures and characteristic properties as well as preparation of the title E (i.e., one of the geometrical isomers) forms, with a view to comparative study, are reported. Moreover, reactions of those conjugated π-electron systems with TCNE (=tetracyanoethylene) in benzene [and in DMF (=N,N-dimethylformamide)] at 25 °C for 24 h under argon yield unique products, possessing interesting molecular structures, respectively, whose characteristic properties and crystal structures are documented, also.     

Practical synthesis of methyl(E)-2-(3-(3-(2-(7-chloro-2- quinolinyl)ethenyl)phenyl)-3-oxopropyl)benzoate,a key intermediate of Montelukast

A novel and practical synthetic route is presented for the preparation of methyl-(E)-2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl) phenyl)-3-oxopropyl)benzoate,the key intermediate of Montelukast,a leukotriene antagonist.The main diarylpropane framework was prepared via a polarity conversation reaction resulting in an acyl anion equivalent followed by a nucleophilic substitution reaction.The overall yield of this approach was 61%.This method is simple for operation and suitable for industrial production.     

3-(Carbazol-2-yl)- and 3-(Carbazol-3-yl)-dl-alanines

A facile transformation of 2- and 3-methylcarbazoles into 3-(carbazol-2-yl)-and 3-(carbazol-3-yl)-dl-alanines compounds is described.     

Pd-catalyzed synthesis of 3-(diarylmethylene)-2-oxindoles and 3-(arylmethylene)-2-oxindoles

An efficient method for the stereoselective synthesis of 3-(diarylmethylene)-2-oxindoles and 3-(arylmethylene)-2-oxindoles via carbopalladation is described. In this approach, an Ugi-4-component reaction (4-CR) adduct was used as the starting material. A one-pot sequence involving intermolecular carbopalladation C-H activation/C-C bond formation efficiently afforded the oxindole derivatives.     

Synthesis and E/Z configuration determination of novel derivatives of 3-aryl-2-(benzothiazol-2'-ylthio) acrylonitrile, 3-(benzothiazol-2'-ylthio)-4-(furan-2'-yl)-3-buten-2-one and 2-(1-(furan-2'-yl)-3'-oxobut-1'-en-2-ylthio)-3-phenylquinazolin-4(3H)-one

Knoevenagel condensation of 2-(benzothiazol-2-ylthio) acetonitrile (2) with either furan-2-carbaldehyde or thiophene-2-carbaldehydes leads to E-isomers 4a-b exclusively, while the condensation of the compound 2 with benzaldehyde or para-substituted benzaldehydes with an electron-donating group afforded E/Z mixtures 4c-e with preferentially formation of the E-isomer. Condensation of furan-2-carbaldehyde (3a) with either 1-(benzothiazol-2'-ylthio) propan-2-one (5) or 2-(2'-oxo propylthio)-3-phenyl-quinazolin-4(3H)-one (9) leads exclusively to the Z-isomers of 6 and 10, respectively. The structures of the newly synthesized compounds were elucidated by elemental analyses, 1H-NMR and 13C-NMR spectra, COSY, HSQC, HMBC, NOE, MS and X-ray crystallographic investigations.