吡唑类化合物的合成研究进展

吡唑类化合物是一类重要的药物合成中间体,在抗肿瘤、抗病毒、抗抑郁等领域发挥着重要作用。本文综述了吡唑类衍生物的合成方法,包括1,3-亲电化合物与肼类的环化、1,3-偶极体系的环加成等。     

三（取代吡唑）硼氢化钾的合成

三（取代吡唑）硼氢化钾的合成郭胜利李贤均（四川大学化学系成都６１００６４）殷元骐（中国科学院兰州化学物理研究所兰州７３００００）关键词取代吡唑硼氢化合成中图分类号Ｏ６１４自１９６７年ＴｒｏｆｉｍｅｎｋｏＳ．［１］首次报道了多聚吡唑硼氢化钾ＫＨｎＢｐｚ...     

取代吡唑啉衍生物的合成与生物活性

采用α-三唑-β-烷氧基芳酮与肼关环,制备了1,3-二苯基-4-三唑基吡唑啉1a,1-苯基-3-对氯苯基-4-三唑基吡唑啉1b和3-取代苯基-4-三唑基吡唑啉(7),并研究了化合物7的成环优化条件.使用α,β-不饱和酮与肼关环合成了1,3,4,5-多取代吡唑啉衍生物1c-1h,并初步用质谱法确定了该反应产物的结构;同时,以3,5-二取代吡唑啉(6)和7作为中间体合成了1-,3-,4-或5-取代的化合物2a-2l.初步生物活性测定结果表明,所合成的化合物均有一定的杀菌、激素和除草效果.     

取代吡唑啉睡物的合成与生物活性

采用α－三唑－β－烷氧基芳酮与肼关环，备了１，３－二苯基－４－三唑基吡唑啉１ａ，１－苯基－３－对氯苯基－４－三唑基吡唑啉１ｂｔ ３－ｂｃ ｗａ ａｓｇ ａｄ －４－ｄｇ ｋｗｗ ａｄ ｋｘｘ ｋｗｗ ｋｓｓ （７）     

通过环化反应构建多取代咪唑的最新研究进展

咪唑是一类非常重要的五元含氮杂环化合物,在有机合成化学中具有广泛的用途,其广泛存在于天然产物、应用药物和材料等领域中,而且也是一类重要的有机合成中间体,因此合成咪唑的方法也倍受人们的关注.归纳总结了通过环化反应构建多取代咪唑的最新研究进展,主要介绍了以肟酯、2H-氮杂环丙烯、酮类化合物、2-氨基吡啶、叠氮化合物、三唑类...     

姜黄素-N-取代吡唑类衍生物合成及抑菌活性

为了寻求杀菌剂的新的先导化合物,用姜黄素与取代酰肼反应得到13个新的姜黄素-N-取代吡唑类衍生物,其结构经IR,1H NMR,13C NMR,MS和元素分析所表征,初步抑菌实验结果表明,在1×10-4mol/L浓度下,所有衍生物与姜黄素对比,对枯草杆菌、金黄色葡萄球菌、大肠杆菌、青霉、黑霉有较好的抑菌效果.其中,3,5-二(4-羟基-3-甲氧基苯基乙烯基)-N-脒基吡唑(3c),3,5-二(4-羟基-3-甲氧基苯基乙烯基)-N-(苯并噻唑-2-硫基乙酰基)吡唑(3k),3,5-二(4-羟基-3-甲氧基苯基乙烯基)-N-(香豆素-3-甲酰基)吡唑(3m)有优异的抑菌效果(抑菌圈16.34～23.81 mm).这些结果表明含有噻唑环、脒基、香豆素环取代基可能有助于提高姜黄素-N-取代吡唑类衍生物的活性.     

取代苯基吡唑类化合物的合成及其除草活性

以1′-(4-氯-2-氟-5-甲基苯基)-4′,4′,4′-三氟-1,3-丁二酮为原料,合成了一系列具有取代苯基吡唑结构的新化合物.化合物结构经¹HNMR,IR,CIMS和元素分析确认.初步生物活性测试表明,所合成的化合物对阔叶杂草具有较高的活性.     

吡唑肟醚类化合物的合成

以1-取代苯基-3-甲基-5-吡唑酮为起始原料,合成了6个具有肟醚结构的新吡唑化合物,其结构经^1H NMR,IR和元素分析确认。     

新型4-双取代吡唑啉酮合成子的合成

吡唑啉酮类化合物是一类功能强大的合成子,具有多取代、多活性位点的特性,目前关于4-双取代吡唑啉酮合成子的研究相对较少。本研究以4-无取代吡唑啉酮为起始原料,在温和简便的条件下,顺利构建了一系列4-氯取代的4-双取代吡唑啉酮化合物(4a～4i),分离收率为66%～91%,其结构经¹H NMR、¹³C NMR和HR-MS(ESI)表征。4a成功参与1,3-偶极反应,在常温条件下,以46%的收率得到新型[3+2]环加成产物。     

2,6-吡啶二甲酰双吡唑衍生物的合成

合成了4个吡唑及其衍生物,其结构经元素分析,IR,1^HNMR和^13CNMR等表征。     

Substituted Pyrazoles and Their Heteroannulated Analogs—Recent Syntheses and Biological Activities

Pyrazoles are considered privileged scaffolds in medicinal chemistry. Previous reviews have discussed the importance of pyrazoles and their biological activities; however, few have dealt with the chemistry and the biology of heteroannulated derivatives. Therefore, we focused our attention on recent topics, up until 2020, for the synthesis of pyrazoles, their heteroannulated derivatives, and their applications as biologically active moieties. Moreover, we focused on traditional procedures used in the synthesis of pyrazoles.     

Soluble Polymer-Supported Synthesis of Pyrazoles via 1,3-Dipolar Cycloaddition Strategy

Rapid parallel liquid-phase synthesis of pyrazoles has first been developed. The 1,3-dipolar cycloaddition between nitrilimines generated in situ and soluble polymer-supported alkynyl or alkenyl dipolarophiles in parallel one-pot fashion gave the corresponding PEG-supported regioisomeric pyrazoles or regiospecific pyrazolines. The latter was assuredly oxidated by DDQ to PEG-supported regiospecific pyrazoles. Cleavage from the support under mild conditions afforded pyrazoles in good yields and high ouritv.     

Synthesis of Novel 1,3,5-Trisubstituted Pyrazoles as Potential Hypoglycemic Agents

A novel series of 1,3,5-trisubstituted pyrazoles was synthesized. Thus, ethyl 2,4-dioxo-6-phenylhex-5-enoate (I) was condensed with phenylhydrazine to afford 3-ethoxycarbonyl-1-phenyl-5-styrylpyrazole (II) which on fusion with hydrazine hydrate gave the corresponding acid hydrazide (III). Reaction of III with the appropriate isothiocyanate yielded the disubstituted thiosemicarbazides (IVa-e) which were cyclized into thiotriazoles (Va-e), thiadiazoles (Vla-e) and oxadiazoles (VIIa-). The structure of the newly synthesized compounds was elucidated by elemental analyses, IR and ¹H NMR spectra.     

Multicomponent Reaction for Synthesis of N-Arylsulfonyl Pyrazoles

A synthesis of functionalized N-arylsulfonyl pyrazoles from the multicomponent reaction of arylsulfonyl hydrazones and dialkyl acetylenedicarboxylates in the presence nucleophilic compounds such as pyridine, isoquinoline, or triphenylphosphine, in good yields, is described.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resources: Full experimental and spectral details.]     

Synthesis of β-Aminoethyl-substituted Pyrazoles

Methods have been developed for the synthesis of 3,5-dimethyl-4-(2-N-mono- and -disubstituted and also unsubstituted aminoethyl)pyrazoles from 1,1-diacetylcyclopropane.     

Synthesis of Polysubstituted Ferrocenesulfoxides

The purpose of the study is to design synthetic methodologies, especially directed deprotometalation using polar organometallic reagents, to access polysubstituted ferrocenesulfoxides. From enantiopure 2-substituted (SiMe₃, PPh₂) S-tert-butylferrocenesulfoxides, a third substituent was first introduced at the 5 position (SiMe₃, I, D, C(OH)Ph₂, Me, PPh₂, CH₂NMe₂, F) and removal of the trimethylsilyl group then afforded 2-substituted ferrocenesulfoxides unreachable otherwise. Attempts to apply the “halogen dance” reaction to the ferrocenesulfoxide series led to unexpected results although rationalized in light of calculated pK_a values. Further functionalizations were also possible. Thus, new enantiopure, planar chiral di- and trisubstituted ferrocenes have been obtained, in addition to several original 2-substituted, 2,3- and 2,5-disubstituted, 2,3,5-trisubstituted and even 2,3,4,5-tetrasubstituted ferrocenesulfoxides, also enantiopure.     

噻唑并嘧啶类化合物的合成研究进展

综述了在医药和农药领域具有广泛用途的噻唑并嘧啶类化合物近二十年来合成方法上的研究进展. 结合本研究组在这一领域的工作介绍了噻唑并嘧啶类化合物的三种主要结构类型: 噻唑并[3,2-a]嘧啶、噻唑并[4,5-d]嘧啶、噻唑并[5,4-d]嘧啶类化合物的相关合成方法及新进展.     

Dess-Martin高价碘化合物在有机合成中的应用进展

简单介绍了Dess-Martin高价碘化合物(DMP)的合成方法,重点对DMP在有机合成反应中的最新应用进展进行了概述.