Symthesis of 3-[1-(p-Fluorophemyl)-Pyrazol-3-YL]-Quimoxalimomes

Abstract

3-[1-(p-Fluorophenylhydrazono)-L-threo-2,3,4-tri hydroxybutyl1-2-quinoxalinowe was prepared and trarrsformed to 3-[5-acetoxymetnyl-1-(p-fluorophenyl)-pyrazol-3-yl]-2-quinoxalinone. N-methylation, followed oy dehydrative cyclisation, gave the M-methyl-derivative of the latter pyrazole. Periodate oxidation gave a glyoxalyl derivative whose aldehyde functionality was confirmed by reduction and oximation.     

Spectrophotometric and x-ray crystallographic studies of 1-carbamoylbenz-[c,d]indol-2-ones

On the basis of a measurement of the frequencies and intensities of the stretching vibrations of the amino, amido, and ester groups in the IR spectra, it was established that products of the reaction of N-benzenesulfonylhydroxynaphthalimides with ammonia in alcohol solutipns have a structure of the type of 1-carbamoylbenz[c,d]-indol-2-ones and are not molecules with a seven-membered heterocycle, by analogy with 3-oxido-2-alkylnaphtho[1,8-d,e][1,3] oxoniazepin-1-ones. A determination of the molecular and crystal structure of one of these compounds (C₁₃H₁₀N₂O₂) confirmed this conclusion: The molecule is 1-(N-methylcarbamoyl)benz[c,d]indol-2-one. In the naphthalene ring of the molecule the bond angles at the central bond are deformed analogously to that found in acenaphthene. The intramolecular hydrogen bond O···HN closes a six-membered ring in the molecule. The crystal is constructed from dimers formed by intermolecular hydrogen bonds O···HN.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1110–1114, August, 1984.     

Neospiroenones. Synthesis of 10,11-dimethoxy-1,6,6-trimethyl-5,6,8,12b-tetrahydrobenzo[d,f]indol-4(3H)-one and 10,11-dimethoxy-6,6-dimethyl- 1,5,6,12b-tetrahydrobenzo[d,f]indol-2(8H)-one

The three-component condensation of isobutyraldehyde, 3,4-dimethoxyphenylacetonitrile, and p-methylanisole or anisole in the presence of concentrated sulfuric acid affords neospiroenone systems.     

Fluorescence reagents. I. Derivatization of carboxylic acids,imides and alcohols with 1-chloromethylbenz[c,d]indol-2(1H)-one (CMBI)

The derivatization and fluorodensitometric determination of carboxylic acids (CA), imides and alcohols with 1-chloromethylbenz[c,d]indol-2(1H)-one ( 19 , CMBI) have been studied. Out of a series of fluorescent fused lactams 9-11, 13-15 and 17 , benzindolone 17 was selected and transformed via hydroxymethylbenzin-dolone 18 into CMBI 19. CMBI reacts with CA, diCA and alcohols respectively to yield strongly fluorescent benz[c,d]indol-1-ylmethyl esters 20, 21 (BIM esters) and BIM ethers 22. Phenobarbital is transformed by action of CMBI into fluorescent 1,3-bisBIM phenobarbital 25. Studies on the applicability of the derivatization reactions to the fluorodensitometric determination of CA, alcohols and imides showed that CA with more than 3 carbon atoms can be determined via BIM esters down to the low picomole range. In the case of alcohols and imides the results were not satisfying. The ir, uv, fluorescence, nmr and mass spectra of the prepared benzindole derivatives are also presented.     

Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols

Structural alteration of the N^b-substituents of psilocin (3-[2-dimethylamino)ethyl]indol-4-ol) ( 12a ) has led to a number of compounds containing known pharmacophoric groups. Further, it is hoped that the subtle changes in the nature of these substituents may lead to a clearer understanding of the structure-activity relationships of the 4-hydroxytryptamine hallucinogens.     

Psilocin analogs. 1. Synthesis of 3-[2-(dialkylamino)ethyl] -and 3-[2-(cycloalkylamino)ethyl] indol-4-ols

The synthesis of four dialkyl and three eyeloalkyl analogs of psilocin (4, R - CH₃), a hallucinogenic principle found in certain fungi, is described. The synthetic route involves four transformations starting with 6,7-dihydroindol-4(5H)one: (1).     

Synthesis of (2S,3S)-[3-(2)H1]-4-methyleneglutamic acid and (2S,3R)-[2,3-(2)H2]-4-methyleneglutamic acid

(2S,3S)-[3-(2)H1]-4-Methyleneglutamic acid 1a and (2S,3R)-[2,3-(2)H2]-4-methyleneglutamic acid 1b have been synthesised for use in biosynthetic and metabolic studies.     

Synthesis,Crystal Structure and Luminescent Property of Cadmium Complex Based on 2-（2-（1Hbenzo[d]imidazol-2-yl）benzyl）-1H-benzo[d]-imidazole

The complex [Cd(bbb)Cl2]·DMF·H2O, where bbb is 2-(2-(1H-benzo[d]imidazol-2-yl)benzyl)-1H-benzo[d]imidazole, was synthesized and characterized by X-ray single-crystal structure analyses. For the complex: C24H25Cl2CdN5O2, Mr = 598.77, crystal system, triclinic, space group P1, a = 9.9878(12), b = 10.0008(12), c = 13.2217(15) , α = 80.674(2), β = 72.158(2), γ = 86.776(2)°, V = 1240.5(3) 3, Z = 2, Dc = 1.598 g/cm3, λ = 0.71073, μ(MoKα) = 1.127 mm–1, F(000) = 600, S = 1.04, R = 0.0905 and wR = 0.3088 for 4805 observed reflections with I 2σ(I). It is a neutral complex. The distorted tetrahedral geometry of cadmium ion is coordinated by two nitrogen atoms of ligand and two chloride ions. The complex emits blue green luminescence with emission peaks at 480 nm in DMF solution.     

Synthesis of N 1 -Substituted,N 3 -[ P -(3-Ethoxy-Carbonyl-4,5-Dihydronaphtho[1,2- c ]Pyrazol-2-YL)Benzenesulfonyl]Urea and Thiourea Derivatives. Class of Cyclooxygenase-2 Inhibitors

Several urea and thiourea derivatives ( 2a-f ) were prepared by the reaction of dihydronaphthopyrazolylbenzenesulfonamide ( 1 ) with the corresponding isocyanates and isothiocyanates, respectively. The benzenesulfonylthioureas ( 2d , e ) were cyclized with ethyl bromoacetate, ethyl g -bromopropionate and f -bromoacetophenones to give the corresponding 4-oxothiazolidine ( 3a , b ), 4-oxo-5,6-dihydrothiazine ( 4a , b ) and thiazoline derivatives ( 5a-d ) respectively.     

Synthesis, Crystal Structure and Antibacterial Activities of 3-[3-Methyl-（2-thienyl）methyl-enehydrazinocarbonyl]-（1H）-1,2,4-triazole

1 INTRODUCTION Azole derivatives, such as the derivatives of pyra- zole, imidazole, triazole including benzotriazole, te- trazole and indole, have extensive biological activi- ties. They have become the central focus of studies of agricultural chemicals, medicines, plant growth regulating agents and so on[1, 2]. Schiff bases also constitute a good type of biologically active sub- structures. Studies on pyrazole Schiff base-type fun- gicides have been reported[3, 4]. However, some struc- …