Synthesis of thiopyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]furo[3,2-d]pyrimidines

<正>Reactions of the 6-hydroxy-thiopyrano[3,4-c]pyridine-5-carbonitrile derivative 1 withα-halo-carbonyl compounds gave the ortho-substituted intermediates 2a-c which were converted into furo[2,3-b]thiopyrano[4,3-d]pyridines 3a-c by fusion of a furan moiety under basic conditions.Further cyclization of 3a-c led to a fusion of a pyrimidine ring,yielding the tetracyclic products 6,7 and 8.In addition,condensation of 6 with various aromatic aldehydes afforded the corresponding imines 9a,b.Mannich reaction of 7 gave products 10a,b.     

One-Step Syntheses of Tetrapyrido[2,3-a:3′,2′-c:2″,3″-h:3″, 2″ ′-j] Phenazine and Dibenzo[a:c](Dipyrido[2,3-h:2′,3′-j]) Phenazine

The one-step syntheses of two fully aromatic planar bis-terdentate bridging ligands are described.     

Synthesis of dihydro-10H-pyrano[3′,4′: 5,6]pyrido[3,2:4″,5″]-thieno[3″,2″-d][3,1]oxazines and pyrimidines

Convenient methods have been developed for synthesizing dihydro-10H-pyrano[3,4:5,6]-pyrido[3,2:4,5]thieno[3,2-d][3,1]-oxazines and -pyrimidines. Optimum conditions have been established for the chlorodeoxygenation of condensed thieno-pyrimidin-4-ones.A. L. Mndzhoyan Institute of Fine Organic Chemistry, Armenian Academy of Sciences, Yerevan, 375014. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 250–253, February, 1995. Original article submitted November 15, 1994.     

Synthesis of New Pyrido[4″,3″:4″,5″]thieno[2″,3″:4,5]pyrimido[2,1-b][1,3,4]thiadiazine Derivatives

Ethyl 2-methyl-11-oxo-9, 10-dihydro-1 H , 11 H -pyrido[4",3":4',5']thieno[2',3':4,5]pyrimido[2,1-b][1,3,4]thiadiazine-8(7 H )-carboxylate 7 has been synthesised by the reaction of ethyl 3-amino-4-oxo-2-thioxo-1,3,4,5,6,8-hexahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(2 H )-carboxylate 2 with allylbromide followed by treatment with bromine and subsequent dehydrobromination of the brominated product 5 with ethanolic sodium hydroxide. Its isomeric ethyl 2-methyl-11-oxo-9,10-dihydro-3 H ,11 H -pyrido[4",3Prime;:4',5']thieno[2',3':4,5]pyrimido[2,1-b][1,3,4]thiadiazine-8(7 H )-carboxylate 8 has been obtained by condensation of 2 with chloroacetone followed by cyclization of the intermediate 9 with p -toulenesulfonic acid. The thiadiazino derivatives 11 , 13 , 15 were prepared through the reaction of 2 with the appropriate f -halocarbonyl compounds followed by cyclization reactions of the intermediates 10 , 12 , 14 .     

4′, 4″-Dihydroxy-3′,5′,3″,5″-tetrabrom-1,4-diphenyl-naphthalin-2, 3-dicarbonsäure-anhydrid

Ohne Zusammenfassung     

Synthesis and Quantum Chemistry Study of Novel Bifurazano [3,4-b : 3′, 4′-f] furoxano [3″, 4″-d] oxacyclohetpatriene

以3,4-双(4′-硝基呋咱-3′-基)氧化呋咱为原料,设计并合成了新型双呋咱并[3,4-b∶3′,4′-f]氧化呋咱并[3″,4″-d]氧杂环庚三烯(1),收率50.1％,其结构经13C NMR,15N NMR,IR,MS和元素分析表征.最佳的反应条件为:以无水碳酸钠为催化剂,乙腈(含水量0.04％)为溶剂,于80℃反应3.5h.用B3LYP方法在6-31G**基组水平上对1的结构进行了计算,得到了稳定的几何构型和键级.在振动分析的基础上求得体系在不同温度下的热力学性质,得到了温度对热力学性能影响的关系式.1的性能研究表明,1的m.p.92℃～94℃,爆速8 256m·s-1(1.85 g·cm-3),摩擦感度0％(90°摆角),撞击感度12％(10 kg,25 cm),特性落高H50 =57.5 cm(5 kg).     

Chromeno[3″,4″:5′,6′]pyrido[2′,3′:4,5]thieno[3,2-e]pyridine—A New Heterocyclic System. Synthesis and Molecular and Crystal Structures

Russian Journal of Organic Chemistry - Multicomponent condensation of cyanothioacetamide, 4-fluoro-2-methylbenzaldehyde, methyl 4-methyl-3-oxopentanoate, and 3-(2-bromoacetyl)-2H-chromen-2-one...     

SYNTHESIS OF NEW RING SYSTEMS: ISOMERIC 1,2,4-TRIAZOLOPYRIMIDO [4″,5″:4′,5′]THIENO[3′,2′:5,6]PYRIDO[3,2C]CINNOLINES AND OTHER RELATED SYSTEMS

3-Amino-2-Cyano-4-(p-tolyl)thieno[3′,2′:5,6]pyrido[3,2-c]cinnoline 1 underwent ring closures with formamide and carbon disulphide to afford pyrimidothienopyridocinnaline 2 and its pyrimido-9,11-thione derivative 3, respectively. Treatment of 1 with triethylorthoformate followed by hydrazine hydrate produced 10-amino-11-imino-pyrimido system 5, which in turn reacted with triethylorthoformate, acetic acid, carbon disulphide, and acetylacetone to cyclize into the systems, 1,2,4-triazolo, 2-methyltriazolo, triazolo-2-thione, and 1,2,4-triazepinopyrimido thienopyridocinnolines 6– 8, 11, respectively. Similarly, 3-amino-2-carboxamido-thienopyridocinnoline 12 was reacted with triethylorthoformate to give pyrimidothienopyridocinnoline-11-one 13, which was treated with phosphorous oxychloride and then hydrazine hydrate to produce 11-hydrazinopyrimido system 16. Treatment of 16 with triethylorthoformate, acetic anhydride, carbon disulphide, and ethyl chloroformate afforded the systems, 1,2,4-triazolopyrimidothienopyrido-cinnoline derivatives 16– 18, 20, respectively.     

Synthesis of Novel Pyrrylthieno[2,3-d]Pyrimidines and Related Pyrrolo[1″,2″:1″,6″]Pyrazino[2″,3″:4,5]Thieno[2,3-d]Pyrimidines

4-Methyl-2-phenyl-5-(1-pyrryl)-6-substituted-thieno[2,3-d]pyrimidines ( 3a-c , 4a-c , 5a , b , and 6 ) have been synthesized. Some of the substituents in position 6 were used to build up different sulfur-, nitrogen- and/or oxygen-containing heterocyclic rings at that position. The 4-methyl-2-phenyl-5-(1-pyrryl)-thieno[2,3-d]pyrimidine-6-carboazide ( 20 ) was also used as a key intermediate in the synthesis of the target pyrrolo[1",2":1',6']pyrazino[2',3':4,5]thieno[2,3-d]pyrimidines.     

Syntheses,Structure, and Luminescent Property of a New 2D Nd(III) Coordination Polymer Based on 4′-(4-Carboxyphenyl)-4,2′:6′,4″-Terpyridine

Russian Journal of Coordination Chemistry - A new lanthanide coordination polymer (Ln-CP) based on Nd(III), [Nd2(Cptpy)2(Glu)2(H2O)2]n · 5n(H2O) (Ι) (HCptpy =...     

Facile synthesis and characterization of novel pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-4(3H)-one and pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine incorporating 1,3-diarylpyrazole moiety

4-(3-(4-Hydroxyphenyl)-1-phenyl-1H-pyrazol-4-yl)-6-phenyl-2-thioxo-1,2-di hydro-pyridine-3-carbonitrile (1) reacted with ethyl chloroacetate (2) in ethanolic sodium acetate solution to yield the corresponding ethyl (3-cyanopyridin-2-ylsulphanyl)acetate derivative 3. Intramolecular cyclization of compound 3 was achieved by its heating in DMF containing potassium carbonate to afford the corresponding ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate derivative 4 which reacted with hydrazine hydrate in refluxing pyridine to yield the starting material 3-aminothieno[2,3-b]pyridine-2-carbohydrazide derivative 7. Compound 7 reacted with different reagents such as triethylorthoformate, formic acid, acetic acid and acetic anhydride to afford the target molecules pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-4(3H)-one derivatives 8–10, 12 and 13 in good to excellent yields. On the other hand, pyridine-2(1H)-thione derivative 1 reacted with hydrazine hydrate in refluxing pyridine to give the other starting material 3-amino-1H-pyrazolo[3,4-b]pyridine derivative 20 which reacted with acetylacetone under reflux to afford the target molecule pyrido[2′,3′:3,4]pyrazolo[1,5-a]-pyrimidine derivative 21 in a good yield. The structures of target molecules were elucidated using elemental analyses and spectral data.     

Effect of solvent on the crystal structures of copper(II) complexes based on 4′-(4-methoxyphenyl)-2,2′:6′,2″-terpyridine and 4′-(3-chlorophenyl)-2,2′:6′,2″-terpyridine

Four homoleptic copper(II) complexes, [Cu(Meophtpy)₂](ClO₄)₂ (Meophtpy = 4′-(4-methoxylphenyl)- 2,2′:6′,2″-terpyridine) (I), [Cu(Meophtpy)₂](ClO₄)₂ · 2H₂O (II), [Cu₂(m-Clphtpy)₄](ClO₄)₄ (m-ClPhtpy = 4′-(3-chlorophenyl)-2,2′:6′,2″-terpyridine) (III), and [Cu₂(m-ClPhtpy)₄](ClO₄)₄ (IV) have been synthesized by hydrothermal methods and characterized by IR, elemental analysis and single crystal X-ray diffraction (CIF files CCDC nos. 963375 (I), 885457 (II), 963377 (III), and 963376 (IV)). Complex II is a polymorph of I and complex IV is a polymorph of III. All these complexes are obtained with 95% ethanol solution or 50% ethanol solution and the solvent control on the crystallization are obviously found. In all complexes, the face-to-face interactions between pyridyl rings or phenyl rings facilitate the construction of 3D network in the crystal in addition to hydrogen bonds. The fluorescence properties of these complexes have been investigated.     

Formation of 3a′,8′-dimethyl-3a′,5′-dihydro-1′H,3′H-dispiro-[cyclohexane-1,3′-furo[3,4-f][2]benzofuran-5′,1″-cyclohexane]-1′,7′(4′H)-dione in the reaction of 3-acetyl-4-methyl-1-oxaspiro[4.5]dec-3-en-2-one with potassium hydroxide

3a′,8′-Dimethyl-3a′,5′-dihydro-1′H,3′H-dispiro[cyclohexane-1,3′-furo[3,4-f][2]benzofuran-5′,1″-cyclohexane]-1′,7′(4′H)-dione was synthesized by reaction of 3-acetyl-4-methyl-1-oxaspiro[4.5]dec-3-en-2-one with potassium hydroxide in water.