Cyclopentanone in the Synthesis of Fused 4,7-Phenanthroline Derivatives

Catalytic condensation of cyclopentanone with arylmethylene(6-quinolyl)amines gave previously unknown 8-aryl-10,11-dihydro-9H-cyclopenta[a]-4,7-phenanthrolines.     

Phendione in the Synthesis of Annelated Derivatives of 4,7-Phenanthroline

By condensation of 5-phenyl-1,3-cyclohexanedione with 6-quinolylamine and aldehydes of aromatic, heterocyclic, and cyclohexene series new 12-aryl(heteryl, cyclohexenyl)-9-phenyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-ones were prepared. The presence of diastereomers in the target reaction products was determined by ¹H NMR spectroscopy.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 5, 2005, pp. 742–748.Original Russian Text Copyright © 2005 by Gusak, Tereshko, Kozlov.     

Synthesis of Amino and Hydroxy Derivatives of 4,7-Phenanthroline

Nitro-, dinitro-, and hydroxynitrophenyl-substituted 4,7-phenanthrolines were reduced with tin(II) chloride in a mixture of acetic and nitric acids to obtain amino, diamino, and hydroxy derivatives of 4,7-phenanthroline. When heated with aromatic aldehydes, the products form azomethines of the 4,7-phenanthroline series.     

Synthesis of Fused Derivatives of 4,7-Phenanthroline by Condensation of 6-Aminoquinoline with Aromatic Aldehydes and Dimedone

8-Aryl-11,11-dimethyl-7,8,9,10,11,12-hexahydrobenzo[a]phenanthrolin-9-ones were obtained by condensation of 6-aminoquinoline with aromatic aldehydes and dimedone.     

Vanillin Esters of Aliphatic Acids in the Synthesis of 4,7-Phenanthroline Derivatives

Condensation of vanillin esters of aliphatic acids with 6-aminoquinoline and cyclic c-diketones (1,3-cyclohexanedione and dimedone) afforded new 2-methoxy-4-(11-oxo-7,8,9,10,11,12-hexahydrobenzo[b][4,7]phenanthrolin-12-yl)phenyl esters of carboxylic acids.     

Synthesis of 1,3-diaryl-4,7-phenanthrolines

A number of new 1,3-diaryl-4,7-phenanthrolines were synthesized by heterocyclization of arylidene-6-quinolylamines with acetophenones in the presence of an acidic catalyst. Intermediate amino ketones and side products, viz., N-(R¹-benzyl)-6-quinolylamines and ,-unsaturated ketones, were isolated. The IR, UV, PMR, and mass spectra of the synthesized compounds are discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1398–1401, October, 1985.     

Synthesis of 4,7-Phenanthroline Derivatives by Condensation of Arylmethylene(6-quinolyl)amines with Hydroxy- and Nitro-substituted Acetophenone

Condensation of arylmethylene(6-quinolyl)amines with hydroxy- and nitro-substituted acetophenones was used to synthesize 1,3-diaryl-4,7-phenanthrolines containing hydroxy and nitro groups in the phenyl rings.     

Synthesis of Some Novel Fused Azole Derivatives

A novel synthesis of pyrazolopyrimidine derivatives was reported wherein 5-amino-1-benzoyl-3-(methylthio)-1H-pyrazole-4-carbonitrile was treated with formic acid, formamide, thioacetamide, carbon disulfide, and phenylisocyanate and phenylisothiocyanate.     

Synthesis of Thiazole and Fused Thiazolo Derivatives

The syntheses of thiazole and fused thiazolo derivatives 2 – 4 , 6 – 8 , 10a – 11b , 13 – 16 from heterocylic isothiocyanates 1 , 5 , 9 , and 12 bearing an ortho ester group and bifunctional reagents, such as substituted propargylamines, is described. Different regioselectivity of intramolecular nucleophilic attack of the thiourea S-atom on the C ? C bond, resulting in the formation of both thiazolo and thiazino derivatives, as well as NMR structure elucidation are discussed.     

1,3-二羟基丙酮衍生物的合成

以五氧化二磷为引发剂 ,二甲亚砜氧化 1,3 二芳氧基 (烷氧基 ) 2 丙醇化合物合成了一系列 1,3 二羟基丙酮衍生物 .通过IR和1HNMR对化合物进行了表征     

Synthesis of 3-substituted and 1,3-disubstituted 4,7-diazaindoles

On the basis of a study of electrophilic substitution reactions (the Mannich reaction and bromination) it was shown that 4,7-diazaindoles react with greater difficulty with soft electrophilic agents than indoles or 4- and 7-monoazaindoles. 3-Substituted and 1,3-disubstituted 4,7-diazaindoles containing amino(dialkylamino)alkyl substituents in the 1 or 3 positions were synthesized.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 848–852, June, 1976.     

Versatile Synthesis of Fused Tricyclic 1,2,4-Triazole Derivatives

ABSTRACT

A rapid and general method for the synthesis of symmetrical disulfides involves reaction of sulfur with sodium hydroxide under PTC-microwave irradiation condition to give sodium disulfide, which reacts with alkyl halides to afford the disulfides in good to excellent isolated yields.     

Synthesis of Dihydrothienopyridine Derivatives Fused with Triazole Rings

New dihydro[3,2‐c][1,2,4]triazolo[4,3‐a]pyridines were synthesized by the reaction of 4‐(methylsulfanyl)‐6,7‐dihydrothieno[3,2‐c]pyridine with acid hydrazides. One bis(dihydrothienotriazolo‐pyridine) was also prepared. In a few cases, the corresponding intermediate could be detected by LC‐MS. The bromophenyl derivative was involved in Suzuki and Sonogashira cross‐coupling reactions. © 2013 Wiley Periodicals, Inc. Heteroatom Chem 24:226–233, 2013; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.21087     

Applications of Azoalkenes in the Synthesis of Fused Ring Pyridazine Derivatives

Cyclic ketohydrazones containing α‐methylene group are oxidized by chloramine‐T followed by treatment with triethylamine leads to the formation of azoalkenes via azochloride, which are trapped by olefinic compounds to produce fused ring pyridazine derivatives in good yield.     

Synthesis and Structure of Tetrahydro-4,7-ethanoisobenzofuran-1,3-dione Derivative

(1R,2R,3S,4R,7R)‐7‐Isopropyl‐6‐methylbicyclo[2.2.2]oct‐5‐ene‐2,3‐dicarboxylic acid anhydride (tetrahydro‐4,7‐ethanoisobenzofuran‐1,3‐dione derivative) adduct 2 was prepared via the isomerization of α‐pinene and β‐pinene in turpentine followed by the Diels‐Alder cycloaddition with maleic anhydride in the presence of phosphoric acid/iodine catalysis. The molecular structure of adduct 2 was characterized by IR, ¹H NMR, ¹³C NMR, ¹H‐¹H COSY, DEPT, HSQC, HMBC, 2D NOESY and MS spectra. The single crystal X‐ray crystallographic analysis of adduct 2 was performed, and the X‐ray powder diffractive spectrum of the sample adduct 2 is consistent with the diffractive spectrum calculated from the single crystal data. Therefore the structure and stereochemistry of adduct 2 was established based on extensive spectral data and single crystal X‐ray analysis.     

卤代-1,3-丁二烯衍生物的合成研究进展

卤代-1,3-丁二烯衍生物是重要的有机合成子, 在构筑环状化合物方面表现出独特的性质, 在功能材料、有机合成等领域有重要的应用价值, 因此其合成方法备受关注. 综述了卤代-1,3-丁二烯衍生物的合成方法, 并展望了其应用前景.     

Alumina Catalyzed Synthesis of Fused Thioxopyrimidine Derivatives Under Microwaves

Abstract

An expeditious solventless approach for the synthesis of pyrazolino[3,4-d]/isoxazolino[3,4-d]/pyrano[2,3-d]/iminopyrimidino[4,5-d]/thioxopyrimidino[4,5-d]/thiazino[5,4-d] pyrimidines from 2-thiobarbituric acid using supported reagents (acidic/basic alumina) under microwave irradiation (MWI) is described. The reaction times were brought down from hours to minutes with yield enhancement. Also the procedure highlights the versatility of solid supports.     

Design and Synthesis of Fused and Spiro Pyrazole Derivatives

Russian Journal of Organic Chemistry - Condensation of 5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one with p-hydroxybenzaldehyde in alcoholic sodium hydroxide yielded...     

氢化喹啉及其芳(杂)环稠合衍生物的合成

通过环己二酮与β-二腈基苯乙烯的Michael加成得到2-氨基-3-氰基-4-芳基-5-氧代-1,4,5,6,7,8-六氢喹啉(1); 4-苯基六氢喹啉(1a)与环己二酮发生胺的加成缩合反应生成2-N-(3-氧代-1-环己烯基)氨基-3-氰基-4-苯基-5-氧代-1,4,5,6,7,8-六氢喹啉(2), 在碱性和氯化亚铜催化下进一步环合成4-苯基-5-氨基-二-(2-氧代环己烷)并[b,g]-1,3-二氢萘啶(3). 芳醛、α-萘胺和环己二酮在乙醇中共回流, 则一锅法完成9-芳基-5,6,7,8,9,10-六氢苯并[c]吖啶酮(4)的合成. 对合成中所涉及的化学反应机理进行了尝试性的讨论. 新化合物1a～4c均经IR, ¹H NMR 及元素分析证明其结构.