Synthesis of 2-(3-hydroxy-2-methyl-1-alkenyl)-1-pyrrolines and 2-(3-hydroxybutyl)-1-pyrroline using α-lithiated 2-methyl-1-pyrroline

Condensation of 2-methyl-1-pyrroline with chloroacetone or 3-chloro-2-butanone using LDA in THF afforded novel 2-(3-hydroxy-2-methyl-1-alkenyl)-1-pyrrolines via a peculiar reaction mechanism instead of the anticipated 2-(3-oxobutyl)-1-pyrrolines. The intermediacy of 2-(2,3-epoxy-2-methylalkyl)-1-pyrrolines in the latter transformation was demonstrated by immediate reductive epoxide ring opening utilizing lithium aluminium hydride in diethyl ether. Furthermore, 2-(3-oxobutyl)-1-pyrroline was prepared via an alternative approach through alkylation of 2-methyl-1-pyrroline with 3-chloro-2-(methoxymethyloxy)-1-propene using LDA in THF, followed by acid hydrolysis. Reduction of 2-(3-oxobutyl)-1-pyrroline by sodium borohydride in methanol afforded the corresponding 2-(3-hydroxybutyl)-1-pyrroline in good yield.     

Synthesis and steric structure of 3,4-dimethyl-2-(3-methyl-1-phenylbuta-1,2-dienyl)-5-phenyl-1,3,2λ<Superscript>5</Superscript>-oxazaphospholane 2-oxide

Allenic 1,3,2-oxazaphospholanes on the basis of d-pseudoephedrine were synthesized. The steric structure of 3,4-dimethyl-2-(3-methyl-1-phenylbuta-1,2-dienyl)-5-phenyl-1,3,2λ⁵-oxazaphospholane 2-oxide was determined by X-ray diffraction.     

Synthesis of 1-alkoxy-3-methyl-1-triazene 2-oxides and 3, 3´-methylene-bis(1-alkoxy-3-methyl-1-triazene 2-oxides)

Russian Chemical Bulletin - A method for the synthesis of 1-alkoxy-3-methyl-1-triazene 2-oxides and their salts with alkali metals was developed. 3,...     

Synthesis and Crystal Structure of 4-Bromo-5-ethoxy-3-methyl-5- （naphthalen- 1-yl）- 1-tosyl- 1H-pyrrol-2（5H）- one

The title compound 4-bromo-5-ethoxy-3-methyl-5-(naphthalen-1-yl)-1-tosyl-1H- pyrrol-2(5H)-one 1 (C24H22BrNO4S, Mr = 500.40) has been synthesized and its crystal structure was determined by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21/n with a = 8.8562(15), b = 18.118(3), c = 14.055(2) , β = 99.855(3)o, V = 2221.9(6) 3, Z = 4, Dc = 1.496 g/cm3, μ = 1.975 mm-1, λ = 0.71073 , F(000) = 1024, R = 0.0607 and wR = 0.1371.     

Synthesis and Crystal Structure of 2（1-Phenyl-3-methyl-5-chloro-1H-pyrazol-4-yl）-3-（1-naphthoylamido）-4-thiazolidinone

1INTRODUCTIONManypyrazolederivativeshavebeenreportedtoshowvariousbiologicalactivitiestobeusedasbactericide[1],fungicide[2],herbicide[3],insecticide[4]andvirucide[5]agents.Inaddition,4-thiazolidinoneplaysavitalroleowingtoitswiderangeofbiologi-calactivities…     

Synthesis,Photochromism and Crystal Structure of 1-（2-Cyano-l,5-dimethyl-4-pyrryl）-2- [2-methyl-5- （3-pyridyl）-3-thienyl]perfluorocyclopentene

A new family of photochromic diarylethene compounds, 1-（2-cyano-l,5-dimethyl- 4-pyrryl）-2-[2-methyl-5-（3-pyridyl）-3-thienyl]perfluorocyclopentene （lo） having an unsymmetrical pyrryl and thienyl substituted hexafluorocyclopentene unit, was synthesized and its structure was determined by X-ray analysis. The crystal belongs to triclinic system, space group PI with a = 8.897（7）, b = 10.139（8）, c = 12.361（9） A, α = 85.222（7）, ρ = 75.439（7）, γ = 78.736（8）°, Z = 2, V= 1057.8（14） A3, D,.= 1.468 mg/m3, p = 0.220 mm-1, F（000） = 476, the final R = 0.0608 and wR = 0.1754 for 3199 observed reflections （1 〉20（/））. Interestingly, compound 1 exhibits good photochromic properties with alternate irradiation of UV light and visible light （〉 510 nm） to form two photoisomers in hexane solution and crystal phase.     

A Novel Photochemical Reaction of 4-Bromo-3-methyl-1- phenyl-4,5-dihydro-pyrazol-5-one

UV-Irradiation of 4-bromo-3-methyl-l-phenyl-4,5-dihydro-pyrazol-5-one (1) in the presence of various aromatic hydrocarbons gave different types of photoproducts depending on the nature of the hydrocarbons via an electron-transfer mechanism. In the presence of naphthalene or phenanthrene a photochemical homocoupling reaction of 1 occurred to form 2 or 2 and 3, respectively.     

Nucleophilic reactions of 1-methyl-2-methoxy-2-phenyl-3-oxo-2,3-dihydroindole

The title compound (1) was prepared via methylene blue (MB)-sensitized photooxy-genation of l-methyl-2-phenylindole (2d) in methanol. Acid-catalyzed nucleophilic substitution of 1 with nucleophiles gave 1,2,2-trisubstituted 3-oxo-2,3-dihydroindoles (3-6). Reduction of 1 with lithium aluminum hydride, followed by acidic workup yielded 4d and 2d, whereas the same reduction reaction of 1, followed by neutral workup gave l-methyl-2-phenyl-3-hydroxy-2,3-dihydroindole (15), together with 3. The reaction pathways of nucleophilic substitution and reduction of 1 were discussed.     

Crystal Structure of 3-Methyl-4-methoxy-3-(3-methyl-4- methoxy-2-benzofuranyl) -2-H-benzofuranyl

1　ＩＮＴＲＯＤＵＣＴＩＯＮ3ｍｅｔｈｙｌ4ｈｙｄｒｏｘｙｂｅｎｚｏｆｕｒａｎｉｓａｎｉｎｔｅｒｍｅｄｉａｔｅｕｓｅｄｆｏｒｔｈｅｓｙｎｔｈｅｓｉｓｏｆｎａｔｕｒｅｐｒｏｄｕｃｔｓ[1].Ｉｔｈａｓｂｅｅｎｓｙｎｔｈｅｓｉｚｅｄｆｒｏｍ1,3ｄｉｈｙｄｒｏｘｙｂｅｎｚｅｎｅ[2-3].Ｔｏｓｙｎｔｈｅｓｉｚｅａｂｉｅｔａｎｅｑｕｉｎｏｎｅｄｉｔｅｒｐｅｎｏｉｄｓｗｉｔｈｉｔ[4,5],ｗｅｉｎｔｅｎｄｅｄｔｏｐｒｏｔｅｃｔｔｈｅｈｙｄｒｏｘｙａｔｔａｃｈｅｄｔｏｉｔｗｉｔｈＭｅ2ＳＯ4.Ｆｉｎａｌｌｙ,ｔｗｏｃｏｍｐｏｕ…     

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.     

Synthesis and Antibacterial Activities of 4-Amino-3-(1-aryl-5-methyl-1,2,3-triazol-4-yl)-5-mercapto-1,2,4-triazoles/2-Amino-5-(1-aryl-5-methyl-1,2,3-triazol-4-yl)-1,3,4-thiadiazoles and Their Derivatives

ＩｎｔｒｏｄｕｃｔｉｏｎＳｃｈｉｆｆｂａｓｅｓ ,ａｍｉｄｅｓ ,ｉｍｉｄａｚｏｌｏ[2 ,1 ｂ] 1,3,4 ｔｈｉａｄｉａｚｏｌｅｓ,ａｎｄ 7Ｈ ｓ ｔｒｉａｚｏｌｏ[3,4 ｂ] 1,3,4 ｔｈｉａｄｉ ａｚｉｎｅｓｃｏｎｔａｉｎｉｎｇｈｅｔｅｒｏｃｙｃｌｅｓｈａｖｅｂｅｅｎａｔｔｒａｃｔｉｎｇｍｕｃｈａｔｔｅｎｔｉｏｎａｓｐｏｔｅｎｔｉａｌａｎｔｉｆｕｎｇａｌａｇｅｎｔｓ .1 51,2 ,3 ｔｒｉａ ｚｏｌｅ ,6 7ｍｅｒｃａｐｔｏ 1,2 ,4 ｔｒｉａｚｏｌｅ ,81,3,4 ｔｈｉａｄｉａｚｏｌｅ9 10ａｎｄｔｈｅｉｒｒｅｌａｔｅｄｃｏ…     

Synthesis and Crystal Structure of 2[1-（1,1-Dimethylethyl）-5-methyl-1-H-pyrazol-4-ylcarbonyl]-N-phenyldrazinecarbothioamide

1INTRODUCTIONThiosemicarbazidespossessingNC=Sgroupareanessentialstructurefeatureresponsibleforvariousbiocidalproperties[1～7].Moreover,theyaretheconvenientandkeyintermediatesforthesyn-thesisofheterocycliccompoundssuchas1,3,4-thiadiazoles,1,2,4-triazoleand…     

Vapor–liquid equilibrium of binary mixtures of trichloroethylene with 1-pentanol, 2-methyl-1-butanol and 3-methyl-1-butanol at 100 kPa

Isobaric vapor–liquid equilibria (VLE) have been obtained for the systems trichloroethylene+1-pentanol, trichloroethylene+2-methyl-1-butanol and trichloroethylene+3-methyl-1-butanol at 100 kPa using a dynamic still. The experimental error in temperature is ±0.1 K, in pressure ±0.1 kPa, and in the liquid and vapor mole fraction ±0.001. The three systems satisfy the point-to-point thermodynamic consistency test. All the systems show positive deviations from ideality. The data have been correlated with the Margules, van Laar, Wilson, NRTL and UNIQUAC equations.     

Synthesis and Crystal Structure of 1-[(1′-Phenyl-5′-methyl-4′-pyrazolcarbonyl)- 3-methylthio-5-amino-1H-yl-1,2,4-triazole

1INTRODUCTIONTheCIDT(N-cyanoimido-S,S-dimethylthiocarbo-nate)hasbeenwidelyutilizedinorganicsynthesisduringthelasttwodecadesandhasbecomeveryusefulforconstructingfunctionalizedheterocyliccom-poundsbecauseoftheirversatility.MuchattentionhasrecentlybeenfocusedonthedevelopmentofCIDTaswellastheirsyntheticapplications[1～4].Meanwhile,manypyrazoleandtriazolederivativesarereportedtoshowvariousbiologicalactivities,suchasantifungal[5],herbicidal[6～8],insectcidal[9]andotheractivities[10～12].Thu…     

Transition metal(II) complexes of 1-(α-hydroxynaphthyl)-2-(3′-methyl-5′-mercapto-1′,2′,4′-triazole)-2-aza-ethane

Summary Binuclear metal complexes of the type [M(HMTE)-(H₂O)₂]₂, where HMTE=1-(-hydroxynaphthyl)-2-(3-methyl-5-mercapto-1,2,4-triazolc)2-aza-ethane and M-Cu^II, Co^II, Ni^II and Mn^II have been prepared and characterized. An octahedral geometry around the metals is proposed. The complexes have been screened as possible fungicides.     

Synthesis,Crystal Structure and Biological Activity of 1-（β-D-Glucopyranosyl）-3- amino-5-methyl-1H-1,2,4-triazole

The title compound 1-（β-D-glucopyranosyl）-3-amino-5-methyl- 1H- 1,2,4-triazole was synthesized and characterized by IR, 1H-NMR and elemental analysis. Its single crystals of 2H2O adduct suitable for X-ray analysis were obtained by the slow evaporation of a H2O solution and its structure was determined by single-crystal X-ray diffraction. The crystal belongs to orthorhombic, space group P212121 with a = 7.7490（15）, b = 10.424（2）, c = 17.447（4） A^°, V = 1409.3（5） A^°^3, Z= 4, C9H20N4O7, Mr = 296.29, Dc = 1.396 g/cm^3,μ = 0.120 mm^-1, S = 1.007, F（000） = 632, R = 0.0686 and wR = 0.1560 for 1217 observed reflections with I 〉 20（I）. The title molecules are linked through intermolecular hydrogen bonds to form two 1-D chain structures, and such adjacent chains are further linked by intermolecular hydrogen bonds and H2O bridges to form a 3-D supramolecular network structure. The preliminary bioassay results showed that the title compound exhibits fungicidal activities against Gibberella zeae and Colletotrichum orbiculare.     

Oxiranyl β-aminovinyl ketones. 5. Transformation of 2-methyl-2-(1-halogenoalkyl)-3(2h)-furanones into oxiranyl β-aminovinyl ketones

In reaction with amines 2-methyl-2-(1-halogenoalkyl)-3(2H) furanones form S-amino-1-halogeno-3-hydroxy-2-methyl-4 penten-3-ones and 6-amino-2-halogeno-3-hydroxy-3-methyl-5-hexen-3-ones, which are converted by the action of bases into the corresponding oxiranyl -aminovinyl ketones.Belorussian State University, Department of Organic Chemistry and Chemistry of High-Molecular Compounds, Minsk. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 609-612, May, 1995. Original article submitted April 11, 1995.     

Utility of 2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-N′-phenylaceto-hydrazonoyl bromide as precursor for synthesis of new functionalized heterocycles

2-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-N′-phenylaceto-hydrazonoyl bromide was synthesized and used as precursor for synthesis of some new 1,3,4-thiadiazoles, pyrrolo[3,4-c]pyrazoles, and 1,2,4-triazolo[4,3-a]pyrimidines. The mechanisms that account for formation of products were discussed. Also, the structures of all the newly synthesized products were confirmed based on elemental analysis, spectral data and by alternative methods.