桥连的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]的合成

2-氨基-4-三氟甲基-5-甲基-噻吩-3-羧酸乙酯(1)与三苯基膦、六氯乙烷及三乙胺反应,以84％的产率得到膦亚胺2.在碳酸钾的催化下,膦业胺2与芳基异氰酸酯和双官能亲核试剂的串联氮杂Wittig反应制得新型桥连的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]3,产率为58％～82％.所有产物结构经IR,1HNMR,MS表征和元素分析确证.     

选择性合成双[噻吩并[2,3-d]嘧啶-4(3H)-酮]

以2-氨基-4-三氟甲基-5-甲基-噻吩-3-羧酸乙酯(1)为起始原料制得膦亚胺2.在碳酸钾的催化下,膦亚胺2与芳基异氰酸酯和伯二胺的氮杂Wittig反应制得嘧啶环上2,2’取代的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]3;膦亚胺2与烷基异氰酸酯和伯二胺的氮杂Wittig反应制得嘧啶环上3,3’取代的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]4.化合物3的核磁共振氢谱表明关环反应在嘧啶环的2,2’位;化合物4的核磁共振氢谱表明关环反应在嘧啶环的3,3’位.对合成反应机理的推导及目标产物核磁共振氢谱数据的分析解释了此合成反应的选择性.     

2-烷(芳)氧基苯并呋喃并[3,2-d]嘧啶-4(3H)-酮衍生物的合成及杀菌活性

应用膦亚胺3与芳基异氰酸酯的氮杂Wittig反应, 生成碳二亚胺4, 4再分别与酚、醇作用, 在碳酸钾或醇钠催化下关环, 以72%～88%的产率合成了2-烷(芳)氧基取代-苯并呋喃并[3,2-d]嘧啶-4(3H)-酮衍生物5和6, 其结构经IR, 1H NMR, MS和元素分析证实. 初步生物活性测试表明该类化合物表现出温和的杀菌活性. 如5f在50 mg/L浓度时, 对黄瓜灰霉菌的抑制率为55%.     

新型2-氨基-呋喃并[2,3-d]嘧啶-4(3H)-酮衍生物的合成及抗肿瘤活性

报道应用aza-Wittig反应,采用易得的原料,在温和的条件下,以78%～90%的产率有效的合成了新型2-氨基-呋喃并[3,2-d]嘧啶-4(3H)-酮衍生物5,其结构经IR,1H NMR,MS和元素分析确认.为进一步得到结构确认,化合物5c经X射线衍射分析证实.运用噻唑蓝(MTT)标准法对化合物5进行了体外抗肿瘤活性的测定,其中5f对肺癌细胞A459的IC50值为18.4μmol/L,显示出潜在良好的抗肿瘤活性.     

利用串联的氮杂Wittig反应方便合成3-[取代吡啶(噻唑)甲基]-1,2,3-三唑[4,5-d]嘧啶-7-酮及其除草活性

用串联的氮杂Wittig关环反应合成了一系列3-[取代吡啶(嘧啶)甲基]-1,2,3-三唑[4,5-d]嘧啶-7-酮.膦亚胺4和芳基异氰酸酯发生氮杂Wittig反应生成碳二亚胺5,继而在乙醇钠催化下与各种脂肪伯胺关环,以较好的收率得到目标产物7.初步生物活性测试结果表明:该系列部分化合物在100 mg/L的浓度下对双子叶植物油菜显示出较好的除草活性.     

5,6,7,8-四氢苯并[4,5]噻吩并[2,3-d]嘧啶-4(3H)-酮类查尔酮的设计、合成及体外抗肿瘤活性

以环己酮、氰乙酸乙酯、硫粉和吗啉为原料,依次通过Gewald反应、关环反应、Chan-Lam偶联反应和Claisen-Schmidt缩合反应以23.9%-40.9%的总收率合成了18个新型5,6,7,8-四氢苯并[4,5]噻吩并[2,3-d]嘧啶-4(3H)-酮类查尔酮化合物,所有化合物结构经过了¹H NMR和MS的确证。初步的生物活性测试表明,目标化合物对乳腺癌MCF-7和MDA-MB-231细胞均显示出抑制活性。      

新型N-酰基-7-甲氧基-苯并[4,5]噻唑并[2,3-c][1,2,4]三唑-3(2H)-硫酮的合成及其除草活性

为了寻找新的含苯并噻唑稠杂环农药先导化合物,以2-氨基-6-甲氧基苯并噻唑为起始原料,经肼化、环化和酰基化反应,合成出了14个N-酰基-7-甲氧基苯并[4,5]噻唑并[2,3-c][1,2,4]三唑-3(2H)-硫酮,并利用1H NMR,ESI-MS及元素分析对其结构进行表征.对目标化合物进行初步的除草活性筛选,实验结果表明:在浓度为200 mg/L时,大部分化合物对黄瓜(Cucumis sativus)、小麦(Triticum aestivum)、高粱(Sorghum vulgare)、萝卜(Raphanus sativus)、油菜(Brassica campestris)和稗草(Echinochloa crusgalli)的根和茎的抑制率在85%以上.     

四氯化锆催化合成嘧啶并[4,5-b]喹啉-2,4(1H,3H)-二酮和11H-茚[1,2-b]喹啉-11-酮

以四氯化锆为催化剂,靛红、1,3-二甲基巴比妥酸/1,3-茚二酮在脂肪醇中能够通过多组分串联反应,有效地转化成为相应的稠环化合物嘧啶并[4,5-b]喹啉-2,4(1H,3H)-二酮和11H-茚[1,2-b]喹啉-11-酮,并巧妙地在这些含氮杂环中引入酯基.这些未见文献报道的化合物均通过了1H NMR、13C NMR、I...     

3,6-二烷硫基-1-苯基-吡唑并[3,4-d]嘧啶-4-酮衍生物的合成与除草活性

通过3-甲硫基-1-苯基-吡唑并[3,4-d]嘧啶-6-硫酮和卤代烃RX(BrR'Br)亲核取代反应合成了16种标题化合物,其结构使用元素分析、IR,1H NMR及LC-MS进行了表征.初步的生物活性测试表明,部分化合物对单、双子叶植物根的生长具有优异的抑制作用.     

2-二烷氨基-3-苯基-5-甲基-6-(1H-1,2,4-三唑-1-基)-噻吩并[2,3-d]嘧啶-4(3H)-酮衍生物的合成及其杀菌活性

用烯基膦亚胺与苯基异氰酸酯、仲胺的串联aza-Wittig反应合成了8个新的2-二烷氨基-3-苯基-5-甲基-6-(1H-1,2,4-三唑-1-基)-噻吩并[2,3-d]嘧啶-4(3H)-酮衍生物(6a～6h),其结构经1H NMR, MS和元素分析表征.初步生物活性测试结果表明,部分6表现出一定的抑菌活性,其中6f在浓度为5×10-5g·L-1时,对棉花炭疽菌的抑制率达到87%.     

Synthesis and biological evaluation of novel thiazolo[4,5-d]pyrimidin-7(6H)-ones as topoisomerase I inhibitors

Chemistry of Heterocyclic Compounds - A series of novel thiazolo[4,5-d]pyrimidin-7(6H)-ones were designed, synthesized, and evaluated as anticancer agents. Among them, two compounds demonstrated...     

Synthesis of[1,2,4]Oxadiazolo[4,5-a]thiazolo[2,3-b]pyrimidin-9(10H)-ones via 1,3-Dipolar Cycloaddition of Nitrile Oxide to Thiazolo[3,2-a]pyrimidin-3-one Derivatives

A new class of [1,2,4]oxadiazolo[4,5‐a]thiazolo[2,3‐b]pyrimidin‐9(10H)‐one was prepared in moderate yields by the reaction of nitrile oxide with 2‐arylmethylidene‐6,7‐dihydro‐5H‐thiazolo[3,2‐a]pyrimidin‐3‐one. The reaction site of dipolarphile is the C?N of thiazolo[3,2‐a]pyrimidin‐3‐one rather than the expected C?C of arylmethylidene. The structures of the products were characterized thoroughly by IR, elemental analysis, MS, and NMR analysis.     

Preparation of benzo[4,5]thiazolo[3,2-a]chromeno[4,3-d]pyrimidin-6-one derivatives using MgO-MgAl2O4 composite nano-powder

MgO-MgAl₂O₄ nanocomposite was prepared from the co-precipitation of Mg(NO₃)₂ and Al(NO₃)₃ salts, characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDS) and fourier transform infrared spectroscopy (FTIR) techniques and evaluated in the synthesis of thirty five derivatives of benzo[4,5]thiazolo[3,2-a]chromeno[4,3-d]pyrimidin-6-ones (d₁-d₃₄) via the multi-component reaction of 4-hydroxycoumarins, aldehydes, and 2-aminobenzothiazole derivatives under solvent free condition. The catalytic activity of MgO-MgAl₂O₄ nanocomposite and the synthesis of the above mentioned compounds were investigated under thermal solvent free (times: 1.4–3 h; yields: 75–95%), ultrasonic irradiation (US) conditions (times: 1–2.5 h; yields: 69–97%) and using high-speed ball milling (HSBM) technique (times: 0.7–2.5 h; yields: 67–97%). In all cases, the products were obtained in excellent yields. Nuclear Magnetic Resonance (NMR) and MASS spectroscopy were used to characterize the structure of the desired product. The mechanism for the preparation of compounds d₁-d₃₄ was proposed and confirmed by ¹H NMR investigations.     

吡唑并嘧啶-4-酮衍生物的合成与除草活性

吡唑并嘧啶-4-酮衍生物的合成与除草活性;吡唑[3; 4-d]并嘧啶酮;苯氧丙酸酯;aza-Wittig反应;合成;除草活性     

Synthesis of 6-mono- and 5,6-disubstituted 1,2,3-triazolo[4,5-d]pyrimidin-7-ones

The reactions of N-substituted 4-amino-3-benzyl-1,2,3-triazole-5-carboxamides with phosphorus oxochloride and dimethylformamide at 80 °C or with triethyl orthoacetate and acetic anhydride at 160 °C afforded 6-mono- or 5,6-disubstituted 1,2,3-triazolo[4.5-d]pyrimidin-7-ones in 30—85% and 65—90% yields, respectively.     

Synthesis and Crystal Structure of 3-Benzyl-5-cyclohexylamino-6-phenyl-3,6-dihydro-1,2,3-triazolo[4,5-d]pyrimidin-7-one

1 INTRODUCTION A large number of 8-azapurine (1,2,3-triazolo[4,5-d]pyrimidine) derivatives have been synthe-sized in recent years, and many of them are reportedto exhibit broad spectral biological activities, such asthe interesting antifungal[1], antiviral[2], anticancer[3]and antiallergic[4] properties. So far, these compoundshave been prepared by either of the following twomajor routes: annulation of a triazole ring onto apyrimidine ring or a pyrimidine ring onto a triazolering. Mos…     

Synthesis and Vasodilatory Activities of New Pyrazolo[3,4—d] pyrimidin—4—one Derivatives

A series of pyrazole[3,4-d] pyrimidin-4-one derivatives were synthesized and tested for vasodilatory activities. All of them were new compounds and their structures were confirmed by IR,^1H NMR,MS and elemental analysis.