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 .     

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.     

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.     

Studies on Thiazolopyridines. Part 1: Antimicrobial Activity of Some Novel Fluorinated Thiazolo[3,2-a]Pyridines and Thiazolo[2′,3′:1,6]Pyrido[2,3-d]Pyrimidines

Ternary condensation of aromatic aldehydes, malononitrile and thioglycolic acid (2:2:1 molar ratio) in ethanol/piperidine afforded the corresponding thiazolo[3,2-a]pyridines 1a-d . Thiazolo[2',3':1,6]pyrido[2,3-d]pyrimidine 4 was obtained by refluxing of compound 1a with acetic anhydride. Also, thiazolopyrido pyrimidine 6 was produced by refluxing of 1a with triethylorthoformate followed by treatment with hydrazine hydrate. Refluxing 1a with formic acid yielded the thiazolopyridopyrimidine 8 which on chlorination with thionyl chloride furnished the chloro derivative 9 . Finally, amino thiazolo[2',3':1,6]pyrido[2,3-d]pyrimidine 10 was obtained by treatment of 1a with formamide. The structures of these compounds were established on the basis of elemental analyses, IR, 1 H NMR, and mass spectral data. Also, the antimicrobial activity of some synthesized compounds is reported.     

Pyrido[2,3-d]dipyrimidines 8. Synthesis of pyrrolo(2′,3′∶4,5)pyrido[2,3-d]pyrimidines

The reaction of 1,3-dimethyl-5-chloro-6-nitropyrido[2,3-d]pyrimidine-2,4-dione with CH-acids yielded 5-substituted pyridol[2,3-d]pyrimidines which were used in the synthesis of pyrrolo(2,34,5)pyrido[2,3-d]pyrimidines.For Communication 7, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 800–803, June, 1993.     

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).     

Synthesis of New Derivatives Benzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-d]pyrimidine

Russian Journal of Organic Chemistry - The reactions of 4-methyl- and (RS)-4,6-dimethyl-2-phenyl-5,6-dihydrobenzo[4′,5′]imidazo-[2′,1′:6,1]pyrido[2,3-d]pyrimidines and...     

新型碱性离子液体催化剂高效催化合成吡喃酮[2,3-d]嘧啶酮和[2,3-d]嘧啶衍生物

制备了碱性离子液体1,1'-(丁烷-1,4-二基)双(1,4-二氮杂二环[2.2.2]辛烷-1-ium)羟化物,并采用红外光谱、1H核磁共振谱和pH值分析对其进行了表征.然后将它用于室温研磨条件下高效催化合成吡喃酮[2,3-d]嘧啶酮和[2,3-d]嘧啶.该法步骤简单,反应时间短,产物收率高,无需柱色谱分离,原料易得,且可回收利用.     

Thieno[2,3-b]pyridine-2-carbohydrazide in Polyheterocyclic Synthesis: The Synthesis of Pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine,Pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3]triazine,and Pyrazolyl,Oxadiazolylthieno[2,3-b]pyridine Derivatives

Pyrdine-2(1H)-thione 1 reacted with ethyl chloroacetate 2 to give 2-S-ethoxy-carbonylmethylpyridine derivative 3, which could be cyclized into thieno[2,3-b]-pyridine-2-carbohydrazide derivative 5 by boiling with hydrazine hydrate. The latter compound reacted with cinnamonitrile derivatives 6a, b, triethylorthoformate, formic acid, dimethylformamide-dimethylacetal, and diethyl carbonate to give the corresponding shiff base 7a, b and pyrido[3′,2′;-4,5]thieno[3,2-d]pyrimidine derivatives 10–13 in respective manner. On the other hand, compound 5 also reacted with carbondisulphide and phenyl isothiocyanate to afford the corresponding 2-(1,3,4-oxadiazolo-2-yl)thieno[2,3-b]pyridine derivatives 18 and 22. Finally, compound 5 reacted with some β-dicarbonyl compounds, such as ethyl acetoacetate, acetylacetone and ethyl β-arylazoacetoacetate, to yield the corresponding 2-(pyrazol-1-yl-carbonyl)thieno[2,3-b]pyridine derivatives 24, 25, and 27 respectively.     

One-Pot Synthesis of Thieno[2,3-b]pyridine and Pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine Derivatives

Russian Journal of Organic Chemistry - 2-Acyl-4,5,6-trialkyl-3-aminothieno[2,3-b]pyridines,...     

Synthesis of novel spiro-fused pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidines

New pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidines, with an associated spiro-3,3′-oxindole attachment, were prepared by three-component combinations of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione with a pair of reactants chosen from a pyrazol-5-one, a pyrazole-5-amine, a barbituric acid, or a 6-aminouracil.     

Pyrido[2,3-d]pyrimidines 7. Reactions of 1,3-dimethyl-5,7-dichloro-6-nitropyrido-[2,3-d]pyrimidine-2,4-dione with amines. Synthesis of derivatives of triazolo(4′,5′:4,5)pyrido[2,3-d]pyrimidine

The reaction of 5,7-dichloro-6-nitropyrido[2,3-d]-pyrimidine-2,4-dione with amines gave products of the substitution of one or two chlorine atoms by ammo groups. The catalytic reduction of 6-nitro-5,7-disubstituted pyrido[2,3-d]pyrimidines with hydrogen over palladium oxide on carbon leads to 5,6-diamino- and 5,6,7-triaminopyridopyrimidines, the reaction of which with amyl nitrite in acetic acid gives triazolo(4,5:4,5) pyrido[2,3-d]pyrimidines.For communication 6 see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 398–401, March, 1993.     

新型碱性离子液体催化剂高效催化合成吡喃酮[2,3-d]嘧啶酮和[2,3-d]嘧啶衍生物（英文）

制备了碱性离子液体1,1'-(丁烷-1,4-二基)双(1,4-二氮杂二环[2.2.2]辛烷-1-ium)羟化物,并采用红外光谱、~1H核磁共振谱和pH值分析对其进行了表征.然后将它用于室温研磨条件下高效催化合成吡喃酮[2,3-d]嘧啶酮和[2,3-d]嘧啶.该法步骤简单,反应时间短,产物收率高,无需柱色谱分离,原料易得,且可回收利用.     

吡咯并[2,3-d]嘧啶衍生物的合成方法研究进展

归纳总结了2,4-二氨基吡咯并[2,3-d]嘧啶和2-氨基-4-氧代吡咯并[2,3-d]嘧啶的主要合成方法,并对各方法的优缺点进行了简要评述.参考文献30篇.     

水中吡喃并[2,3-d]嘧啶衍生物的洁净合成

以芳醛、丙二腈和2-氨基-4,6-二羟基嘧啶为原料, 以水为溶剂, 在80 ℃以苄基三甲基溴化铵为催化剂一步合成了一系列的吡喃并[2,3-d]嘧啶衍生物, 产物的结构通过IR, 1H NMR和元素分析表征. 该方法反应条件温和、操作简单、收率高. 而且水作为反应溶剂具有廉价、安全、无污染、产物易于分离的优点.     

苯并噻吩并[3′,2′:2,3]吡啶并[4,5-d]噻唑并[3,2-a]嘧啶酮类衍生物的有效合成

报道了氨基磺酸作用下,通过Pictet-Spengler反应合成苯并噻吩并[3′,2′:2,3]吡啶并[4,5-d]噻唑并[3,2-a]嘧啶酮衍生物的有效合成方法.其中,该反应关键中间体7-(3-氨基苯并噻吩-2-基)噻唑并[3,2-a]嘧啶-5-酮,经由7-氯甲基噻唑并[3,2-a]嘧啶-5-酮与2-巯基苯甲腈的烷基化及Thorpe-Ziegler环化制得.该合成过程原料易得,反应条件温和,收率高,为新型稠杂环嘧啶类化合物的合成提供了简便的新途径.     

Polycyclic N-Heterocyclic Compounds,Part 77: Synthesis of [1]Benzothieno[3′,2′:2,3]oxepino[4,5-d]pyrimidines and Evaluation of Their Antiplatelet Aggregation Activity

Reaction of 3-(3-cyanopropoxy)[1]benzothiophene-2-carbonitrile with sodium hydride gave 5-amino-1,2-dihydro[1]benzothieno[3,2-d]furo[2,3-b]pyridine and 5-amino-2,3-dihydro[1]benzothieno[3,2-b]oxepin-4-carbonitrile. The latter compound served as a convenient scaffold for the synthesis of the new heterocycles [1]benzothieno[3′,2′:2,3]oxepino[4,5-d]pyrimidines and the parent 1,2,4,5-tetrahydro[1]benzothieno[2′,3′:6,7]oxepino[4,5-e]imidazo[1,2-c]pyrimidine heterocyclic system. The new compounds described in this report were evaluated as inhibitors of platelet aggregation in vitro.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.     

Synthesis of 2,4-disubstituted pyrimido[4,5-b]-indoles,pyrano[4′,3′:4,5]pyrrolo[2,3-d]pyrimidines and some conversions of pyrimido[4,5-d]indoles

Methods have been developed for the production of 2,4-disubstituted 5,6,7,8-tetrahydro-9H-pyrimido[4,5-b]indoles and pyrano[43:4,5]pyrrolo[2,3-d]pyrimidines. Heterocyclization reactions were carried out on 4-hydrazinopyrimido[4,5-b]indoles.A. L. Mndzhoyan Institute of Fine Organic Chemistry, National Academy of Sciences of the Republic of Armenia, Erevan, 375014. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10. pp. 1413–1416, October, 1996. Original article submitted June 21, 1996.     

Synthesis of benzothieno[2,3-b]thiophenes, [2,3-b:3′,2′-d]-dithienothiophenes and their selenium derivatives via electrophilic cyclization and McMurry cyclization

Benzothieno[2,3-b]thiophenes, [2,3-b:3′,2′-d]-dithienothiophenes, and their selenium derivatives were synthesized in good yields from readily available 3-ethynyllithio-benzo[b]thiophenyllithio compounds, sulfur or selenium, and 2 equiv of acid chlorides. Two heteroarene rings were constructed by a twofold cyclization via an acid chloride-induced electrophilic ring closing and the McMurry cyclization using Zn/TiCl₄ reagents.     

微波辐射下吡啶[2,3-d]嘧啶衍生物的高效合成

本文以等摩尔的芳醛,巴比妥酸（或1,3-二甲基巴比妥酸）,5-氨基-2-甲基苯[d]噻唑为原料,以醋酸和乙二醇为溶剂,微波辐射下多组分一锅法合成了一系列新的吡啶[2,3-d]嘧啶衍生物。这种方法具有产率高,操作简便,反应时间短等优点。