Article
Chemistry, Organic
Maxime De Abreu, Yue Tang, Etienne Brachet, Mohamed Selkti, Veronique Michelet, Philippe Belmont
Summary: An efficient silver-catalyzed tandem reaction has been developed for the formation of 1,2-dihydroisoquinoline derivatives, providing a straightforward method to access highly functionalized multiheterocyclic scaffolds. This methodology offers a promising route for the synthesis and development of biologically relevant new heterocyclic pharmacophores, and allows for modifications at various sites of this pharmacophore.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Applied
Hongmei Zhu, Lei Chen, Rongxian Bai, Yanlong Gu
Summary: Two classes of indole-tetrahydropyridine hybrid molecules were synthesized via three-component reactions, providing a straightforward approach for accessing diverse molecular structures. The reactions were likely triggered by Michael addition, leading to the formation of indol-3-ylimine intermediate, which was then trapped by the indole component. The resulting indol-3-yl-substituted tetrahydropyridines could be converted into indole-pyridine hybrid molecules with the aid of DDQ.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Biochemistry & Molecular Biology
Igor Yu Grishin, Nikolai A. Arutiunov, Dmitrii A. Aksenov, Nicolai A. Aksenov, Alexander Aksenov, Amina Z. Gasanova, Elena A. Sorokina, Carolyn Lower, Michael Rubin
Summary: In this study, polyphosphoric acid was used as a catalyst to efficiently synthesize 3-(1H-indol-3-yl)benzofuran-2(3H)-ones via condensation reaction between 3-(2-nitrovinyl)-1H-indoles and phenols.
Article
Chemistry, Organic
Aurelien Dupeux, Veronique Michelet
Summary: A novel and mild synthetic route for preparing functionalized polycyclic indole skeletons via gold-mediated cycloisomerization/alkoxylation of 1,6-aldehyde-yne has been developed. This atom-economical catalytic process demonstrated remarkable selectivity in accessing functionalized 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indole derivatives with high synthetic utility. Additionally, it could be optimized under asymmetric conditions with an enantiomeric excess of <= 86%.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Hisashi Masui, Sena Kanda, Shinichiro Fuse
Summary: The authors examined previously reported preparations of (1H-indol-3-yl)methyl halides, clarified inconsistencies within the literature, and developed a highly versatile nucleophilic substitution method using microflow technologies, enabling the synthesis of various indole derivatives.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hao Zhang, Lishan Hu, Kai Yu, Lan-Lan Lou, Shuangxi Liu
Summary: Developing an efficient and convenient method for direct synthesis of bioactive 3-(indol-2-yl)quinoxalin-2(1H)-ones is highly desirable in the pharmaceutical industry. In this work, 3-(indol-2-yl)quinoxalin-2(1H)-ones were synthesized by a one-step electrochemical cross-dehydrogenative coupling process from quinoxalin-2(1H)-ones and indoles. This protocol is simple, operationally convenient, and compatible with a broad range of substrates, enabling the synthesis of the desired coupling products in good to excellent yields (up to 97%) without the use of any catalyst or chemical oxidant. In addition, a reaction mechanism based on the electrochemical oxidation of indoles was proposed.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Shun Tu, Ting-Jian Zhang, Yi Zhang, Xu Zhang, Zhen-Hao Zhang, Fan-Hao Meng
Summary: This study synthesized two series of amide-based XO inhibitors, with compound 3i showing the most promising in vitro inhibitory potency and hypouricemic effect. Molecular simulations provided insights into the interaction modes of representative compounds, supporting compound 3i as a lead for further exploration of amide-based XO inhibitors.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Subhendu Pramanik, Sarat Chatterjee, Rumjhum Banerjee, Chinmay Chowdhury
Summary: This study presents a direct synthesis method for carbazoles containing aryl and aryl ketone groups. The reaction involves Pd(II)-catalyzed cascade reactions, which enables the fast assembly of carbazoles through four carbon-carbon bond formations. The absence of aldehyde substrates leads to the formation of C4-aryl-substituted carbazoles. The method is versatile for the synthesis of biscarbazole derivatives.
Article
Chemistry, Organic
Chunhua Ma, Yue Wang, Guang Chen, Jingyi Li, Yuqin Jiang, Xinying Zhang, Xuesen Fan
Summary: This paper presents the synthesis of 3-(indol-2-yl)succinimide/maleimide and indoyl/pyrrolyl fused benzodiazepine skeletons through the reaction of 2-(1H-indol-1-yl)anilines with maleimides. Mechanistic studies reveal that the formation of these compounds involves Ru(ii)-catalyzed and free amino group-assisted regioselective bond cleavage and coordination reactions. The synthesized compounds show potential as lead compounds for the development of anticancer drugs.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Biochemistry & Molecular Biology
Bastien Champciaux, Clement Raynaud, Albertus Viljoen, Loic Chene, Jerome Thibonnet, Stephane P. Vincent, Laurent Kremer, Emilie Thiery
Summary: This study focuses on the synthesis of 1,7- and 3,4-indole-fused lactones via a simple and efficient reaction sequence, with the evaluation of their activity against Mycobacterium tuberculosis showing that the oxazepino-indole structure is a new inhibitor of M. tuberculosis growth in vitro.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jing Sun, Chen Yan, Qiu Sun, Ying Han, Chao-Guo Yan
Summary: In chloroform, the p-TsOH promoted annulation reaction of 3-(indol-3-yl)maleimides and (indol-2-yl)diphenylmethanols resulted in functionalized pyrrolo[3 ',4 ':6,7]cyclohepta[1,2-b:4,5-b ']diindoles with satisfactory yields, demonstrating a formal [4+3] cycloaddition and an unprecedented rearrangement of the maleimide motif. Alternatively, the reaction of 3-(indol-3-yl)maleimides and 3-hydroxy-3-(indol-3-yl)-indolin-2-ones in acetonitrile produced functionalized spiro[indoline-3,9 '-pyrrolo[3 ',4 ':4,5]cyclopenta[1,2-b]indole] in good yields and with high diastereoselectivity. On the other hand, the p-TsOH promoted reaction of 3-(indol-3-yl)maleimides and 2-hydroxy-2-(indol-3-yl)-indene-1,3-diones yielded functionalized spiro[indene-2,9 '-pyrrolo[3 ',4 ':4,5]cyclopenta[1,2-b]indoles] as major products and spiro[indene-2,9 '-pyrrolo[3 ',4 ':6,7]cyclohepta[1,2-b:4,5-b ']diindoles] as minor products.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Alexander Aksenov, Nicolai A. Aksenov, Elena Aleksandrova, Dmitrii A. Aksenov, Igor Yu Grishin, Elena A. Sorokina, Allison Wenger, Michael Rubin
Summary: The [4+1]-spirocyclization of nitroalkenes to indoles provides a convenient approach to 2-(1H-indol-2-yl)acetonitriles, but can lead to unwanted byproducts. This study offers a solution to effectively transform these byproducts into the desired acetonitrile molecules.
Article
Chemistry, Organic
Qin Shi, Haiyan Hu, Minxing Du, Yajun Sun, Yudong Li, Yuehui Li
Summary: In this study, CO2/H2 was used as a methylation reagent for selective C-H methylation of heteroarenes. The reaction was catalyzed by cobalt/B(C6F5)3, and the Lewis acidic additive B(C6F5)3 played a crucial role in achieving good reactivity. The reaction proceeds via CO2 reduction, C-C bond formation, and reduction. Water is the only byproduct of this environmentally friendly alternative for C-H methylation.
Article
Chemistry, Organic
Axel Sabourin, Jeremy Dufour, Jean-Pierre Vors, David Bernier, Jean-Luc Montchamp
Summary: Various approaches for the preparation of phosphorus-substituted 5- and 6-membered benzophostams are discussed in the text, including carbodiimide-promoted cyclization and copper-catalyzed cross-coupling reactions. The methods for synthesizing P-ethoxy-substituted 5-membered benzophostams are compared in the study.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Anoop Singh, Imtiaz A. Shah, Jyothi Yadav, Preetika Sharma, Rajni Kant, Eldhose Iype, Sravendra Rana, Indresh Kumar
Summary: A simple and straightforward method for the enantioselective synthesis of indol-3-yl-piperidine has been developed, providing good yields and high enantioselectivity.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
