Ruthenium-Catalyzed Decarboxylative C–H Alkenylation in Aqueous Media: Synthesis of Tetrahydropyridoindoles

Jin, Xinchun; Xie, Lu; Liu, An-Di; Li, Xuedong; Wang, Dong; Cheng, Liang; Liu, Li

doi:10.1021/acs.joc.8b00229

Cited by 23 publications

(9 citation statements)

References 69 publications

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“…), 46.4 (NCH 2 ), 30.8 (CH 2 ), 28.9 (CH 2 ); v max 3336, 2979, 1537, 1515, 1447, 1425, 1401, 1383, 1362, 1274, 1171, 1118, 1030, 994, 920, 872, 836, 802, 782, 758, 623, 563, 544, 507; HRMS (ESI+) C 14 H 15 NO 2 [M + H] + exact mass 230.1181, accurate mass 230.1181 (mass error 2.01 ppm). All physical and spectral properties were consistent with those previously described 32,33 …”

Section: Methodssupporting

confidence: 73%

Systematic evaluation of a panel of 30 synthetic cannabinoid receptor agonists structurally related to MMB‐4en‐PICA, MDMB‐4en‐PINACA, ADB‐4en‐PINACA, and MMB‐4CN‐BUTINACA using a combination of binding and different CB₁ receptor activation assays: Part I—Synthesis, analytical characterization, and binding affinity for human CB₁ receptors

Pike

Grafinger

Cannaert

et al. 2021

Drug Testing and Analysis

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Synthetic cannabinoid receptor agonists (SCRAs) are one of the largest and most structurally diverse classes of new psychoactive substances (NPS). Despite this, pharmacological data are often lacking following the identification of a new SCRA in drug markets. In this first of a three-part series, we describe the synthesis, analytical characterization, and binding affinity of a proactively generated, systematic library of 30 indole, indazole, and 7-azaindole SCRAs related to MMB-4en-PICA, MDMB-4en-PINACA, ADB-4en-PINACA, and MMB-4CN-BUTINACA featuring a 4-pentenyl (4en-P), butyl (B/BUT), or 4-cyanobutyl (4CN-B/BUT) tail and a methyl L-valinate (MMB), methyl L-tert-leucinate (MDMB), methyl L-phenylalaninate (MPP), L-valinamide (AB), L-tert-leucinamide (ADB), L-phenylalaninamide (APP), adamantyl (A), or cumyl head group. Competitive radioligand binding assays demonstrated that the indazole core conferred the highest CB 1 binding affinity (K i = 0.17-39 nM), followed by indole-(K i = 0.95-160 nM) and then 7-azaindole-derived SCRAs (K i = 5.4-271 nM). Variation of the head group had the greatest effect on binding, with tert-leucine amides and methyl esters (K i = 0.17-14 nM) generally showing the greatest affinities, followed by valine derivatives (K i = 0.72-180 nM), and then phenylalanine derivatives (K i = 2.5-271 nM). Adamantyl head groups (K i = 8.8-59 nM)

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Section: Methodssupporting

confidence: 73%

Systematic evaluation of a panel of 30 synthetic cannabinoid receptor agonists structurally related to MMB‐4en‐PICA, MDMB‐4en‐PINACA, ADB‐4en‐PINACA, and MMB‐4CN‐BUTINACA using a combination of binding and different CB₁ receptor activation assays: Part I—Synthesis, analytical characterization, and binding affinity for human CB₁ receptors

Pike

Grafinger

Cannaert

et al. 2021

Drug Testing and Analysis

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“…Ji and co‐workers disclosed a Ru(II)‐assisted intramolecular decarboxylative C−H alkenylation of N‐substituted indolyl carboxylic acids to access structurally useful indole‐fused cyclohexanyl acetic acids in aqueous media in 2018 (Scheme 17). [29] Optimization study revealed that the promising result was obtained when molecular oxygen was employed as an oxidant to catalyze these decarboxylative C−H functionalizations. The reaction proceeded in the presence of Cs 2 CO 3 in aqueous media under oxygen, leading to the formation of the cyclized product up to 79% yield.…”

Section: Intramolecular C−c Bond Formationmentioning

confidence: 99%

Ruthenium Catalyzed Intramolecular C−X (X=C, N, O, S) Bond Formation via C−H Functionalization: An Overview

Singh

Chouhan

Mukherjee

2021

Chemistry An Asian Journal

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Ruthenium catalyzed C−H activation is well known for its high tolerance towards the functional group and broad applicability in organic synthesis and molecular sciences, with significant applications in pharmaceutical industries, material sciences, and polymer industry. In the last few decades, enormous progress has been observed with ruthenium‐catalyzed C−H activation chemistry. Notably, the vast majority of the C−H functionalization known in the literature are intermolecular, although the intramolecular variant provides fascinating new structural facet starting from the simple molecular scaffolds. Intramolecular C−H functionalization is atom economical and step efficient, results in less formation of undesired products which is easy to purify. This has created a lot of interest in organic chemistry in developing new synthetic strategies for such functionalization. The focus of this review is to present the relatively unexplored intramolecular functionalization of C−H bonds into C−X (X=C, N, O, S) bonds utilizing versatile ruthenium catalysts, their scope, and brief mechanistic discussion.

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“…[13] To access the structurally useful indole-fused cyclohexanyl acetic acids, in 2018, Liu et al reported the ruthenium-catalyzed decarboxylative CÀ H alkenylation in aqueous media (Scheme 5). [14] Indole-3-carboxylic acid moiety was introduced as a traceless directing group that might stabilize the seven-membered cyclo ruthenium intermediate. This method provides a sustainable and efficient access to various indole-fused cyclohexanyl acetic acids under mild conditions.…”

Section: Indole Alkenylationmentioning

confidence: 99%

Aerobic Oxidative Functionalization of Indoles

et al. 2020

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The synthetic methodology for direct indole functionalizations is of great significance in indole chemistry and has been intensively investigated in the last few decades. From the perspective of green chemistry, oxygen is the best choice as the terminal oxidant in molecular synthesis. Hence, aerobic oxidative functionalization of indoles became a hot research topic in the last decade. Numerous efficient protocols in this field have been discovered that enable facile and efficient transformations of indoles to related valuable compounds, which are summarized and discussed in detail in this review.

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Ruthenium-Catalyzed Decarboxylative C–H Alkenylation in Aqueous Media: Synthesis of Tetrahydropyridoindoles

Cited by 23 publications

References 69 publications

Ruthenium Catalyzed Intramolecular C−X (X=C, N, O, S) Bond Formation via C−H Functionalization: An Overview

Aerobic Oxidative Functionalization of Indoles

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