Synthesis最新文献

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A Domino One-Pot Approach to Functionalized Benzonitriles from 2-[(3-Hydroxy/acetoxy)propyn-1-yl]benzamides 从 2-[(3-羟基/乙酰氧基)丙炔-1-基]苯甲酰胺制备功能化苯腈的多米诺一锅法

Synthesis

Pub Date : 2024-07-15 DOI: 10.1055/a-2356-8297

Sindoori R. Nair, Bhavani Shankar Chinta, Beeraiah Baire

Functionalized benzonitriles, α,β-epoxyketones and β-hydroxy-α-haloketones are found in numerous medicinally important molecules, whilst benzonitriles in combination with any of these functional groups may be of interest to medicinal chemists. However, the simultaneous incorporation of a nitrile group and these functional groups on the aromatic ring is a challenging task. Herein, we report a strategy for the rapid and simultaneous construction of structurally novel benzonitrile derivatives, possessing either an ortho-α-iodo-β-hydroxyketone, an α,β-epoxyketone or an α,β-enone, from unprotected, 2-[(3-hydroxy/acetoxy)propyn-1-yl]benzamides. This process involves NXS-promoted dehydration–halohydration followed by DIPEA-mediated epoxide formation (from alcohols). We have developed both stepwise and one-pot strategies to improve the synthetic efficiency. No metal catalyst is employed and the method exhibits good substrate scope and yields.

功能化苯腈、α,β-环氧酮和β-羟基-α-卤酮存在于许多具有重要药用价值的分子中，而苯腈与其中任何一个官能团的结合可能会引起药物化学家的兴趣。然而，在芳香环上同时加入腈基和这些官能团是一项具有挑战性的任务。在此，我们报告了一种从无保护的 2-[(3-羟基/乙酰氧基)丙炔-1-基]苯甲酰胺快速同时构建结构新颖的苯甲腈衍生物的策略，这些衍生物具有正α-碘-β-羟基酮、α,β-环氧酮或α,β-烯酮。这一过程包括 NXS 促进的脱水-加氢反应，然后是 DIPEA 介导的环氧化物形成（从醇）。我们开发了分步法和单锅法两种策略来提高合成效率。该方法无需使用金属催化剂，且具有良好的底物范围和产量。

引用次数: 0

SYNFORM ISSUE 2024/8 同步信息》第 2024/8 期

Synthesis

Pub Date : 2024-07-15 DOI: 10.1055/s-0043-1763992

M. Zanda

引用次数: 0

Annulation Reactions of Isoquinolinium Ylides with Sulfamate-Derived Cyclic Imines toward Polycyclic 1,3-Benzoxazepine Heterocycles 异喹啉鎓酰化物与氨基磺酸盐衍生环胺对多环 1,3-苯并氧氮杂环的环化反应

Synthesis

Pub Date : 2024-07-11 DOI: 10.1055/a-2349-6944

Koushik Patra, Sana Mulani, Mahiuddin Baidya

A dearomatization-guided and (3+2) cycloaddition-triggered annulation reaction of in situ formed isoquinolinium ylides with sulfamate-derived cyclic imines is reported, offering a cogent synthesis of tetracyclic 1,3-benzoxazepine frameworks in high yields. The protocol features successive ring-forming and ring-breaking events in a cascade fashion and is also scalable.

报告了一种脱芳烃化引导和（3+2）环加成触发的原位形成的异喹啉鎓酰化物与氨基磺酸盐衍生环状亚胺的环化反应，提供了一种高产率的四环 1,3-苯并氧氮杂卓框架的可靠合成方法。该方法以级联方式连续进行成环和破环，并且可以扩展。

引用次数: 0

Oxidative Cross-Dehydrogenative C–H Bond Amination of Imidazo[1,2-a]pyridines in Aqueous Media under Metal-Free Conditions 无金属条件下水介质中咪唑并[1,2-a]吡啶的交叉脱氢 C-H 键氧化胺化反应

Synthesis

Pub Date : 2024-07-10 DOI: 10.1055/a-2348-4764

Durgesh Sarothiya, Umesh A. Kshirsagar

The metal-free direct oxidative cross-dehydrogenative C–H bond amination of imidazopyridines with pyrazole in water as solvent has been developed under K₂S₂O₈-promoted mild conditions. This strategy was applied to variable imidazoheterocycles to give amination products in moderate to good yields. The described protocol also offers scale-up synthesis for the construction of C–N bonds, which makes it suitable for the synthesis of biologically active compounds and pharmaceuticals.

在 K2S2O8 促进的温和条件下，开发了咪唑并吡啶与吡唑在水作为溶剂的无金属直接氧化交叉脱氢 C-H 键胺化反应。该方法适用于各种不同的咪唑杂环，能以中等至良好的收率得到胺化产物。所描述的方案还提供了构建 C-N 键的放大合成方法，因此适用于生物活性化合物和药物的合成。

引用次数: 0

Spirocyclic Hybrids of Nortropane and 1,3-Oxazinan-2-one Fragments 正托烷和 1,3-恶嗪酮-2-酮片段的螺环杂化物

Synthesis

Pub Date : 2024-07-08 DOI: 10.1055/a-2335-4444

Alexandr Mandzhulo, Iryna Vashchenko, Oleg Lukin, Svetlana Shishkina, Grygoriy Dolgonos, Andrii Gerasov, Vitaliy Yepishev, Dariia Samofalova, Volodymyr Fetyukhin, Alexander Shivanyuk

We report facile and versatile procedures for the synthesis of exo- and endo-isomeric spirocyclic hybrids of pharmacophoric (1R,5S)-8-azabicyclo[3.2.1]octane (nortropane) and 1,3-oxazinan-2-one fragments. Our approach consists of the hydrocyanation of endo- and exo-isomeric N-Cbz-protected nortropane-3-spiroepoxides, the reduction of hydroxy nitriles into amino alcohols, the synthesis of N-alkylated amino alcohols via reductive amination, the spirocyclization of the amino alcohols, N-alkylation of the unsubstituted 1,3-oxazinan-2-one fragment in the spiro compounds, and removal of the Cbz protecting groups.

我们报告了用于合成药效(1R,5S)-8-氮杂双环[3.2.1]辛烷（去甲丙烷）和 1,3-氧氮杂环-2-酮片段的外异构体和内异构体螺环混合物的简便而多用途的程序。我们的方法包括：对内向异构体和外向异构体进行 N-Cbz 保护的去甲托烷-3-螺环氧化物的氢氰化反应、将羟基腈还原成氨基醇、通过还原胺化合成 N-烷基化氨基醇、氨基醇的螺环化反应、螺环化合物中未取代的 1,3-oxazinan-2-one 片段的 N-烷基化反应，以及去除 Cbz 保护基团。

引用次数: 0

Asymmetric Organocatalytic Benzylation of Morita−Baylis−Hillman Carbonates with 2,4-Dinitrotoluene Derivatives 莫里塔-贝利斯-希尔曼碳酸盐与 2,4-二硝基甲苯衍生物的不对称有机催化苄化反应

Synthesis

Pub Date : 2024-07-05 DOI: 10.1055/a-2361-0011

Yu-Da Wu, Bo Huang, Yu-Chun Chen, Jeng‐Liang Han

We here described the organocatalytic asymmetric benzylation of Morita−Baylis−Hillman (MBH) carbonates with 2,4-dinitrotoluene derivatives as nucleophiles. The developed reaction provides a straightforward access to functionalized 2,4-dinitrotoluene derivatives of biological and synthetic relevance. Highly functionalized products have been chemoselectively and efficiently obtained in good to high yield (up to 84%) and with excellent stereoselectivity (up to >20:1 dr, >99 ee).

我们在此描述了以 2,4-二硝基甲苯衍生物为亲核体的森田-贝利斯-希尔曼（MBH）碳酸盐的有机催化不对称苄基化反应。所开发的反应可直接获得具有生物和合成相关性的功能化 2,4-二硝基甲苯衍生物。高官能化产物以良好的化学选择性和高效率获得，收率高达 84%，并具有良好的立体选择性（>20:1 dr，>99 ee）。

引用次数: 0

Efficient Oxidation with Singlet Oxygen from 5,10,15,20-Tetraphenylporphyrin under Blue LED Irradiation and Air Atmosphere: Simplified Preparation of Key Building Blocks for Natural Product Synthesis 在蓝光 LED 照射和空气环境下，5,10,15,20-四苯基卟啉与单线态氧的高效氧化：简化天然产物合成关键组分的制备过程

Synthesis

Pub Date : 2024-07-05 DOI: 10.1055/a-2361-0069

Masato Hasumi, Tomohiro Tsutsumi, Daiki Shikama, Ichiro Hayakawa

A method for preparing important building blocks for natural product synthesis has been developed using singlet oxygen generated from 5,10,15,20-tetraphenylporphyrin (TPP) under blue LED irradiation. Using this method, the allylic oxidation of dicyclopentadiene proceeded smoothly in air atmosphere with an 87% yield. This condition, using TPP under blue LED irradiation, was expanded to include the oxidation of cyclopentadiene. It is a simple and cost-effective method of synthesizing important building blocks for natural product synthesis.

在蓝光 LED 的照射下，利用 5、10、15、20-四苯基卟啉（TPP）产生的单线态氧，开发出了一种用于制备天然产物合成的重要构筑物的方法。利用这种方法，二环戊二烯的烯丙基氧化反应在空气中顺利进行，产率达 87%。在蓝光 LED 的照射下使用 TPP 的这一条件被扩展到环戊二烯的氧化。这是一种简单而经济有效的方法，可用于合成天然产物的重要构筑物。

引用次数: 0

Palladium-Catalyzed Domino Heteroarylation of Thioamides: A Simple Route to Benzothieno[2,3-b]quinolones 钯催化的多米诺硫酰胺异芳基化反应：获得苯并噻吩并[2,3-b]喹啉酮的简单途径

Synthesis

Pub Date : 2024-07-04 DOI: 10.1055/a-2360-8167

M. Janni, Annaram Thirupathi, Subhashini V Subramanian, S. Peruncheralathan

Domino reactions are essential for advancing organic synthesis. This study introduces novel thioamide-based precursors for a palladium-catalyzed selective domino heteroarylation process. The method efficiently produces benzothieno[2,3-b]quinolones with yields ranging from moderate to very good. By employing aryl chlorides, the efficiency of the domino heteroannulation process is comparable to that of aryl bromides. Executing a one-pot, two-step reaction also delivered a single domino product with high selectivity. The strategy involved fine-tuning substituent reactivity, utilizing electron-rich arenes, and forming metallocycles with nucleophilic sulfur, consistently yielding a single product. The proposed mechanism is corroborated by mechanistic studies.

多米诺反应对于推进有机合成至关重要。本研究介绍了用于钯催化选择性多米诺杂芳基化过程的新型硫代酰胺基前体。该方法可高效生产苯并噻吩并[2,3-b]喹啉酮类化合物，产率从中等到非常好不等。通过使用芳基氯化物，多米诺杂芳基化过程的效率与芳基溴化物相当。执行一锅两步反应还能得到高选择性的单一多米诺产物。该策略包括微调取代基反应性、利用富电子烯烃以及与亲核硫形成金属环，从而持续产生单一产物。机理研究证实了所提出的机理。

引用次数: 0

Synthesis of Heterocycles by HNTf2-Catalyzed C−H Functionalization of Vinyldiazo Compounds with 3-Hydroxyisoindolinone 通过 HNTf2 催化乙烯基重氮化合物与 3-羟基异吲哚啉酮的 C-H 功能化合成杂环化合物

Synthesis

Pub Date : 2024-07-04 DOI: 10.1055/a-2360-8359

Michael P. Doyle, Ming Bao, Hadi D Arman

A Brønsted acid catalyzed C−H functionalization of vinyldiazoacetates with 3-hydroxyisoindolinone has been developed. This methodology provides a general access to E-substituted isoindolinone vinyldiazo compounds in good yields and excellent diastereoseletivity with broad substrate generality under mild conditions, and with 4-substituted-2-diazo-3-butenoates produces fused bicyclic pyrrolidines. The reaction generally involves addition of the N-acyl ketiminium electrophile formed from the 3-hydroxyisoindolinone to the vinylogous position of vinyldiazo compounds that results in vinyldiazonium ion intermediates that undergo deprotonation to new vinyldiazo compounds or ring closure to fused bicyclic pyrrolidines.

本研究开发了一种布氏酸催化的乙烯基重氮乙酸酯与 3-羟基异吲哚啉酮的 C-H 功能化反应。该方法提供了一种获得 E-取代的异吲哚啉酮乙烯基重氮化合物的通用方法，在温和的条件下，具有良好的产率和优异的非对映无毒性，以及广泛的底物通用性，并可与 4-取代的-2-重氮-3-丁烯酸盐一起生成融合的双环吡咯烷。反应一般涉及将 3-羟基异吲哚啉酮形成的 N-酰基酮亲电子体添加到乙烯基重氮化合物的乙烯基位置，从而产生乙烯基重氮离子中间体，经过去质子化反应生成新的乙烯基重氮化合物或闭环生成融合的双环吡咯烷。

引用次数: 0

Palladium-catalyzed Asymmetric Trifluoromethylated Allylic Alkylation of Azlactone: Efficient Access to Unsaturated α-Quaternary Stereogenic α-Amino Acid Derivatives 钯催化的氮内酯不对称三氟甲基化烯丙基烷基化反应：高效获取不饱和 α-季立体源性 α-氨基酸衍生物

Synthesis

Pub Date : 2024-07-04 DOI: 10.1055/a-2360-8289

Shuaibo Zhang, Lu Sun, Dong Li, Jinfeng Zhao, Jingping Qu, Yuhan Zhou

An unprecedented strategy for asymmetric trifluoromethylated allylic alkylation of azlactone with α-(trifluoromethyl)allyl acetate catalyzed by a Pd(OAc)2/(R)-BINAP has been rationally designed and developed, providing various unsaturated α-quaternary α-amino acid derivatives bearing trifluoromethyl groups, contigous quaternary and tertiary stereogenic centers in good yields with exclusive regioselectivity and excellent stereoselective control under relatively mild reaction conditions. The scale-up experiment has shown no loss of reactivity and stereoselectivity, the synthetic utility of the current strategy is testified through product transformations to obtain some important bioactivity species.

在钯(OAc)2/(R)-BINAP 催化下，合理设计并开发了一种前所未有的α-(三氟甲基)烯丙基乙酸烯丙酯与氮内酯进行不对称三氟甲基烯丙基烷基化的策略、在相对温和的反应条件下，以良好的产率、独有的区域选择性和出色的立体选择性控制，制备出了各种带有三氟甲基、邻接季基和叔基立体中心的不饱和 α-季α-氨基酸衍生物。放大实验表明，反应活性和立体选择性没有降低，通过产物转化获得了一些重要的生物活性物种，从而验证了当前策略的合成效用。

引用次数: 0

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