Synthesis of 3-methyl-[1,2,4] -triazepino[6,5,4-jk] carbazol-4(3H)one

The title compound ( 14 ), a representative of a novel ring system, was prepared from 9H-carbazole-1-carboxylic acid 1-methylhydrazide ( 7 ) and triethyl orthoformate. Attempted cyclization of 7 with triethyl orthoacetate led only to 9H-carbazole-l-carboxylic acid 2-(l-ethoxyethylidene)-l-methylhydrazide ( 16 ). Treatment of 16 with trifluoroacetic acid gave 9H-carbazole- 1 -carboxylic acid ( 12 ). A postulated mechanism for this transformation was supported by studies with model compounds. A new synthesis of 1 -benzoyl-2-methylhydrazine ( 24 ), using 1-acetyl-1-methylhydrazine ( 22 ) as a synthon, is described.     

Synthesis of 4-[3-(1H)-indolyl]-2-[N-guanidinomethyl]thiazole dihydrochloride

The title compound 3b was synthesized in three steps from acetaminothioacetamide ( 4b ) in 15% overall yield. This represents the first synthesis of a 2-guanidinomethylthiazole, which is a homolog of an important pharmacophore, 2-guanidinothiazole.     

Synthesis of 1-phenyl-3-methyl-4-alkyl-4-[N-methylbutyro(capro)lactyl]-5-pyrazolones

The corresponding hydrazones, which on heating are cyclized to give 1-phenyl-3-methyl-4-alkyl-(benzyl)-4-(2-oxopyrrolidinomethyl)- and 1-phenyl-3-methyl-4-alkyl(benzyl)-4-(N-methylcaprolactyl)pyrazolones, are formed in the reaction of alkyl(benzyl) (2-oxopyrrolidinomethyl)- and alkyl-(benzyl) (N-methylcaprolactyl)acetoacetic esters with phenylhydrazine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1546–1548, November, 1976.     

A study of the Claisen rearrangement of 7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one derivatives

Summary The Claisen rearrangement of 7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (2 a) gave 7-hydroxy-8-(1-phenyl-2-propenyl)-3-phenyl-(4H)-1-benzopyran-4-one (3 a) and 2,3-dihydro-2,6-diphenyl-3-methyl-(7H)furo[2,3-h]-1-benzopyran-7-one (7 a). 2-Methyl-7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (2 b) afforded4 b and7 b. 8-Methyl-7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (12) gave only the alkali soluble product 7-hydroxy-8-methyl-6-(1-phenyl-2-propenyl)-3-phenyl-(4H)-1-benzopyran-4-one (13).3 a,4 b, and13 were further cyclized in acidic medium to9 a,10 b, and14 followed by dehydrogenation.This paper is dedicated to Dr. F. M. Dean, Department of Organic Chemistry, Robert Robinson Laboratories, University of Liverpool, Liverpool, U. K., on his retirement     

Synthesis of 1-[2-(1H-Indol-3-yl)ethyl]-4-acetyl-3-hydroxy-5-phenyl-1H-pyrrol-2(5H)-ones

Russian Journal of General Chemistry - 1-[2-(1H-indol-3-yl)ethyl]-4-acetyl-3-hydroxy-5-phenyl-1H-pyrrole-2(5H)-ones were synthesized by the short heating of a mixture of tryptamine, aromatic...     

Synthesis of benzofuro[3,2-b] quinolin-6(11H) one and derivatives

A new and efficient synthesis of benzof'uro[3,2-b]quinolin-6(11H) one ( 3 ) is reported, by treatment of 2- {[(phenoxy)acetyl]amino} benzoic acid ( 6a ) with polyphosphoric acid. An intermediate in the conversion of 3 to 6a , namely, 2-(3-benzofuranylamino)benzoic acid ( 7 ), was defined. An improved method for the synthesis of 6a is also described, which was used to prepare analogs ( 6b-n ) of 6a . In addition, an 11-alkoxy derivative ( 8 ) and 11-dialkylamino derivatives ( 10 and 11 ) of benzofuro [3,2-b]quinoline were prepared from 3 .     

Synthesis and Structure of 5-Amino-6-(4-fluorophenylamino)-3-methylthio-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

The title compound (C18H15FN6OS) has been synthesized and its crystal structure was determined by X-ray analysis. The crystal belongs to monoclinic system, space group P21/n with a = 13.983(10), b = 7.337(5), c = 16.702(12) (A), α = 90, β = 98.277(12), γ = 90°, V = 1696(2)(A)3, Z = 4, Dc= 1.498 g/cm3, Mr = 382.42,μ = 0.224 mm-1, F(000) = 792, the final R = 0.0362 and wR = 0.0878 for 2579 observed reflections with I ＞ 2σ(Ⅰ). In the title compound, the atoms of C(1),C(2), C(3), C(4), C(5), N(1), N(2), N(3), N(4), N(5), N(6), O(1) and S(1) form a fully delocalized system with the average deviation of 0.0307(A). There exists a part of electron delocalization over the planes of Ⅰ (pyrazolo[3,4-d]pyrimidin-4-one moiety), Ⅱ (phenyl moiety) and Ⅲ (p-fluorophenylamine moiety). In the molecule, intermolecular hydrogen bonds between N(6)-H(6)…O(1)and C( 15)-H( 15)…O( 1 ) are observed.     

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 of 2-phenyl-3-(2-furyl) — and 2-phenyl-3-[β-(2-furyl)vinyl]-1,2-dihydro-naphtho[1,2-d]-1,2,4-triazines

The corresponding 2-phenyl-3-(2-furyl)- and 2-phenyl-3-[-(2-furyl)vinyl]-1,2-dihydronaphtho-[1,2-d]-1,2,4-triazines were obtained by heating Schiff bases [prepared by reaction of 1-(phenyl-azo)-2-aminonaphthalene with furfural, -(2-furyl)acrolein, and their 5-bromo and 5-nitro derivatives] in glacial acetic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 158–160, February, 1973.     

Synthesis and study of new derivatives of 6-[methoxy(phenyl)methyl]-2-(nitroamino)pyrimidin-4(3H)-one

New 6-[(2,6-dihalophenyl)(methoxy)methyl]-5-methyl-2-(nitroamino)pyrimidin-4(3H)-ones were synthesized by an original and efficient method involving regioselective O,O′-dimethylation of substituted mandelic acids in superbasic medium. The compounds obtained can serve as precursors to a novel series of non-nucleoside HIV-1 replication inhibitors.     

Synthesis of 3-(Dialkylamino)-4-halofuro[3,4-c]pyridin-1(3H)-ones

Russian Journal of Organic Chemistry - The reaction of 4-halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with acyclic and alicyclic secondary amines in ethyl acetate afforded the corresponding...     

Synthesis of (s)-1-{3-[4-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmetyl}-3-substituted-urea derivatives as antibacterial agents

A new series of (s)-1-{3-[4-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmetyl}-3-substituted-urea derivatives have been synthesized and characterized with spectral data, such as IR, NMR and Mass spectroscopies. All compounds are in vitro evaluated for their efficacy as antimicrobial agent against the gram-positive pathogenic strains such as Bacillus subtilis ATCC 6633, Staphylococcus aureus ATCC 25923, Staphylococcus epidermidis ATCC 12228 and Streptococcus pyogens ATCC 8668. Five compounds ( 19k , 19l , 19m , 19n and 19o ) out of 15 compounds showed moderate activity.     

Synthesis and characterization of novel 2-(1-benzyl-3-[4-fluorophenyl]-1H-pyrazol-4-yl)-7-fluoro-4H-chromen-4-one derivatives

Novel 1-benzyl-3-(4-fluorophenyl)-1H-pyrazole-4-carbaldehydes 3a to 3e were synthesized via Vilsmeier-Haack reaction of the appropriate 1-benzyl-2-(1-(4-fluorophenyl)ethylidene)hydrazines, derived from 4-fluoroacetophenone 1 with substituted 2-benzylhydrazines 2a to 2e . The base catalyzed condensation of 1-benzyl-3-(4-fluorophenyl)-1H-pyrazole-4-carbaldehydes 3a to 3e with 1-(4-fluoro-2-hydroxyphenyl)ethanone 4 gave (E)-3-(1-benzyl-3-(4-fluorophenyl)-1H-pyrazol-4-yl)-1-(4-fluoro-2-hydroxyphenyl)prop-2-en-1-ones 5a to 5e . On cyclization with dimethyl sulfoxide (DMSO)/I₂, compounds 5a to 5e gave 2-(1-benzyl-3-(4-fluorophenyl)-1H-pyrazol-4-yl)-7-fluoro-4H-chromen-4-ones 6a to 6e . Structures of all novel compounds were confirmed by infrared (IR), proton nuclear magnetic resonance (¹H NMR), carbon nuclear magnetic resonance (¹³C NMR), and mass spectral data. All the synthesized compounds were screened for their antibacterial activities.     

Ring closure of 1-[4-(imidazol-1-yl)phenyl]-3-phenyl-2-propen-1-one derivatives to potential biologically active compounds

1-[4-(Imidazol-1-yl)phenyl]-3-phenyl-2-propen-1-one 1 reacted with acetone cyanohydrin, ethyl phenylacetate and cyanoacetamide to give the adducts 2, 8 and 10 respectively. Action of hydrazine hydrate on both the γ-ketonitrile 2 and the corresponding γ-ketoacid 4 led to pyridazine derivatives 3 and 5 . 4,5-Dihydropyridazinone 5 was dehydrogenated by the action of bromine in acetic acid to give pyridazinone 6 . Cyclization of acid 8 in acetic medium resulted in α-pyrone 9 . Cyanopentanamide 10 was converted with hydrochloric acid into δ-ketoacid 13 which led to α-pyrone 14 via an intramolecular dehydration. Refluxing 10 in the presence of acetic acid and ammonium acetate gave 3,4-dihydropyridone 11 which was dehydrogenated to produce pyridone 12 .     

Synthesis and characterization of poly[4-(4-hydroxyphenoxy) benzoic acid]

Poly[4-(4-hydroxyphenoxy) benzoic acid] was prepared by the bulk polycondensation of 4-(4-acetoxyphenoxy) benzoic acid. Polycondensation was conducted at 350°C for 3 h under a reduced pressure of 0.1 mmHg and gave a polymer with X?n of 255. The polymer was characterized by elemental analysis, IR spectroscopy, differential scanning calorimetry, and wide-angle X-ray measurement. The crystal/nematic and nematic/isotropic phase transition temperatures of polymer, which depend on the molecular weight, were observed at about 300°C and 410°C, respectively. The polymers with low molecular weights showed nematic textures above 300°C. This nematic/isotropic phase transition temperature is lower than that of poly (4-hydroxybenzoic acid). This thermal behavior of polymer comes from ether units, which increase the flexibility (the rotation or torsion of skeletal bonds) of the polymer chain. © 1994 John Wiley & Sons, Inc.     

Synthesis of some 3-alkenyl-4-oxo-1-phenyl-5,6-dihydro-1H,4H, -pyrano[2,3-C]pyrazole derivatives

The title compounds were prepared from 3-alkenyl-1-phenyl-2-pyrazolin-5-one derivatives and α,β-unsaturated acyl chlorides as potential cardiotonic agents.     

The photoaffinity ligand [3,5-3H] 4-azidoclonidine: Synthesis and characterization details

[3,5-³H] 4-Azidoclonidine 6 was prepared from [3,5-³H] 4-aminoclonidine 4 and has emerged as a valuable tool to study the alpha-2-adrenergic receptor. This revised version was published online in July 2006 with corrections to the Cover Date.