Synthesis of 5-Iodo-1,2,3,4-tetrahydropyridines by Rhodium-Catalyzed Tandem Nucleophilic Attacks Involving 1-Sulfonyl-1,2,3-triazoles and Iodides

Man, Zengming; Dai, Haican; Shi, Yinping; Yang, Dongdong; Li, Chuan‐Ying

doi:10.1021/acs.orglett.6b02428

Cited by 44 publications

(11 citation statements)

References 60 publications

(12 reference statements)

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“…The inclusion of NaHCO 3 during Rh-carbene formation has been recently reported by Bao en route to octahydro-1 H -purines . Our work expands the use of inorganic bases during Rh-carbenoid reaction which are rare in the literature …”

supporting

confidence: 52%

A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2H-1,4-oxazines

et al. 2020

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Herein, we report a Rh(II)-catalyzed reaction between 1-tosyl-1,2,3-triazoles and halohydrins to provide 2,6-substituted 3,4-dihydro-2H-1,4-oxazines under basic conditions. The reaction is proposed to undergo a rhodium carbenoid 1,3-insertion into O–H followed by an annulation. The scope includes phenyl or alkenyl C4-substituted triazoles and a range of halohydrins using catalytic Rh2Oct4 and K2CO3. A synthesis of the antimicrobial natural product (±)-chelonin C is also reported using this novel methodology.

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supporting

confidence: 52%

A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2H-1,4-oxazines

et al. 2020

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“…1,2,3-Triazoles are heterocyclic compounds with a wide range of applications in medicinal chemistry, chemical biology, material science, and synthetic organic chemistry [4][5][6][7][8][9][10]. Among them, the 1-aryl-[1,2,3]-triazoles are key building units embedded in the lead compounds currently being developed as σ 2 receptor ligands [11], Hsp90 inhibitors [12], suppressors of estrogen-related receptor α [13].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of ethyl 3-hydroxy-5-methyl-2-(4-(m-tolyl)-1H-1,2,3-triazol-1-yl)-[1,1′-biphenyl]-4- carboxylate, C₂₅H₂₄N₃O₃

Wang

Zhao

Xing

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1536564The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialTo ethynyl-3-methylbenzene (63.8 mg, 0.55 mmol) and ethyl 4-azido-3-oxobutanoate (85.5 mg, 0.5 mmol) in t-BuOH/H 2 O (5 mL, V/V = 1/1) were added CuSO4· 5H 2 O (26 µL, 1M, 5 mmol) and sodium ascorbate (9.9 mg, 10 mmol). The mixture was stirred at room temperature for 12 h. After com- pletion monitoring by TLC, the mixture was charged with 1-buta-2,3-dien-1-one (79.3 mg, 0.55 mmol) and NaOH (40.0 mg, 1.0 mmol), stirred and heated at 80°C for 1.5h. After cooling to room temperature, the reaction mixture was extracted with dichloromethane (3 × 15 mL), and the combined organic layers were dried over anhydrous Na 2 SO4 and concentrated in vacuum. The resulting residue was purified by flash chromatography (SiO 2 ) using EtOAc/ petroleum ether (v/v = 1/5) as the solvent system to give the title compound (143.5 mg, 63%) as yellow solid. Single crystals were obtained by slow evaporation of its chloroform solution at room temperature. Experimental detailsAll H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with U iso (H) set to 1.2Ueq(C) and to 1.5Ueq(C) for methyl groups. . Owing to its larger conjugated system, coplanarity, and capability of hydrogen

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“…N ‐Sulfonyl‐1,2,3‐triazoles have recently emerged as structural motifs that are studied for synthesizing a variety of biologically active heterocycles, [ 6 ] including pyrrole, [ 7 ] tetrahydropyridines, [ 8 ] imidazoles, [ 9 ] pyrroloindoline, [ 10 ] and others. [ 11 ] In these transformations, the highly reactive rhodium azavinyl carbenes (Rh‐AVC), derived from Rh(II)‐catalyzed denitrogenation of N ‐sulfonyl‐1,2,3‐ triazoles has been successfully employed as a [1C], [2C], or aza ‐[3C]‐synthon in various [3+ n ] cycloaddition reactions.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Rh‐Catalyzed Formal [3+2] Cyclization for the Synthesis of 5‐Aryl‐2‐(quinolin‐2‐yl)oxazoles and Its Applications in Metal Ions Probes

Zhou

Zuo

et al. 2021

Chin. J. Chem.

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Main observation and conclusion A facile and efficient strategy for the synthesis of 5‐aryl‐2‐(quinolin‐2‐yl)oxazoles via rhodium‐catalyzed formal [3+2] cyclization of 4‐aryl‐1‐tosyl‐1H‐1,2,3‐triazoles with quinoline‐2‐carbaldehydes has been described. The protocol employs mild conditions and offers good yields of diverse 2,5‐aryloxazole derivatives with a broad reaction scope. It is amenable to gram‐scale synthesis and easily transformation. Moreover, this 5‐aryl‐2‐(quinolin‐2‐yl)oxazole skeleton is indeed a new fluorophore and its applications in metal ions probes are also investigated and showed fluorescent responses to mercury ion.

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Synthesis of 5-Iodo-1,2,3,4-tetrahydropyridines by Rhodium-Catalyzed Tandem Nucleophilic Attacks Involving 1-Sulfonyl-1,2,3-triazoles and Iodides

Cited by 44 publications

References 60 publications

A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2H-1,4-oxazines

A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2H-1,4-oxazines

Crystal structure of ethyl 3-hydroxy-5-methyl-2-(4-(m-tolyl)-1H-1,2,3-triazol-1-yl)-[1,1′-biphenyl]-4- carboxylate, C₂₅H₂₄N₃O₃

Rh‐Catalyzed Formal [3+2] Cyclization for the Synthesis of 5‐Aryl‐2‐(quinolin‐2‐yl)oxazoles and Its Applications in Metal Ions Probes

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Synthesis of 5-Iodo-1,2,3,4-tetrahydropyridines by Rhodium-Catalyzed Tandem Nucleophilic Attacks Involving 1-Sulfonyl-1,2,3-triazoles and Iodides

Cited by 44 publications

References 60 publications

A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2H-1,4-oxazines

A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2H-1,4-oxazines

Crystal structure of ethyl 3-hydroxy-5-methyl-2-(4-(m-tolyl)-1H-1,2,3-triazol-1-yl)-[1,1′-biphenyl]-4- carboxylate, C25H24N3O3

Rh‐Catalyzed Formal [3+2] Cyclization for the Synthesis of 5‐Aryl‐2‐(quinolin‐2‐yl)oxazoles and Its Applications in Metal Ions Probes

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Crystal structure of ethyl 3-hydroxy-5-methyl-2-(4-(m-tolyl)-1H-1,2,3-triazol-1-yl)-[1,1′-biphenyl]-4- carboxylate, C₂₅H₂₄N₃O₃