Application of copper(II)-mediated radical cross-dehydrogenative coupling to prepare spirocyclic oxindoles and to a formal total synthesis of Satavaptan

Hurst, Timothy E.; Gorman, Ryan M.; Drouhin, Pauline; Taylor, Richard J. K.

doi:10.1016/j.tet.2018.09.026

Cited by 9 publications

(6 citation statements)

References 29 publications

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“…The 3‐acetyl oxindoles 126 undergo unexpected deacetylation when they were treated with alumina (Scheme 33) [39]. In 2018, Taylor and co‐workers reported a copper‐mediated oxidative radical cross‐dehydrogenative coupling of cyclic β ‐keto amides 127 [74], which afforded spirocyclic oxindoles 128 in moderate to good yield (Scheme 34).…”

Section: Five‐membered Heterocycles With One Heteroatommentioning

confidence: 99%

The applications of β‐keto amides for heterocycle synthesis

2022

Journal of Heterocyclic Chem

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β-Keto amides have multiple nucleophilic and electrophilic reaction sites within their molecular structures, which make them excellent building blocks for the construction of various heterocyclic compounds. In this Review, we summarized the applications of structurally diversified β-keto amides for the synthesis of (1) Five-membered heterocycles including furans, thiophenes, pyrroles, indoles, pyrazoles, triazoles, and their derivatives; (2) six-membered nitrogen-and oxygen-containing heterocycles such as pyridones, dihydropyridines, pyridines, quinolones, quinolines, pyranones and the like; (3) various lactams and some aza-aliphatic rings. The focus is on the multicomponent reactions which take advantage of the unique versatile reactivities of β-keto amides.

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Section: Five‐membered Heterocycles With One Heteroatommentioning

confidence: 99%

The applications of β‐keto amides for heterocycle synthesis

2022

Journal of Heterocyclic Chem

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“…Based on these findings, we optimized reaction conditions to achieve tandem reduction-cyclization reaction and produce the oxindole 1 using compound 8 as a substrate. As shown in Table 5, addition of a Brønsted or Lewis acid increased oxindole cyclization (entries [1][2][3][4][5][6]. Especially, addition of AcOH or citric acid resulted in prompt cyclization (entries 1 and 2).…”

Section: Figure 3 Reactive Rotamer Effect Induced By α-Substituentmentioning

confidence: 99%

“…Especially, addition of AcOH or citric acid resulted in prompt cyclization (entries 1 and 2). On the other hand, addition of p-toluenesulfonic acid, BF3 OEt2 or AlCl3 afforded the N-hydroxyoxindole 16 as a by-product (entries [3][4][5]. Addition of PPTS increased the production of the N-hydroxyoxindole 16 to 55% yield.…”

Section: Figure 3 Reactive Rotamer Effect Induced By α-Substituentmentioning

confidence: 99%

“…3-methyl-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate 11 (15.2 mg, 19%) 4, 171.1, 137.0, 128.0, 127.7, 123.0, 122.6, 114.9, 82.0, 50.0, 37.5, 27.5, 19.9 Table 5 and Table 6 8, 167.7, 141.1, 129.0, 127.0, 123.7, 122.4, 108.8, 82.8, 55.0, 27.6, 19.3 = 8.4,2.8 Hz),6.96 (1H,td,J = 8.4,2.8 Hz),6.83 (1H,dd,J = 8.4,4. 3, 132.4, 113.3, 110.1, 109.6, 81.3, 56.1, 55.5, 27.3, 19.6 2, 142.8, 128.7, 122.9, 121.8, 109.5, 81.3, 60.7, 27.4, 26.3, 7.9 5, 168.7, 142.2, 138.3, 128.3, 122.3, 110.4, 81.2, 55.4, 27.3, 21.3, 19.6 …”

Section: Cyclization Reaction Of Di-t-butyl 2-(2-aminobenzyl)-2-methymentioning

confidence: 99%

“…2 In fact, various synthetic routes for these oxindoles are described in the literature. [3][4][5][6][7][8][9] Especially, tandem reduction-lactamization, which uses dimethyl or diethyl 2-alkyl-2-(2-nitrophenyl)malonates, is considered one of the most efficient method for preparing these oxindoles. For example, Acheson and co-workers reported that Raney nickel catalyzed hydrogenation of the nitro group of the diethyl 2-methyl-2-(2-nitrophenyl)malonate produces oxindole 3.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Substituted t-Butyl 3-Alkyloxindole-3-carboxylates from Di-t-butyl (2-Nitrophenyl)malonates

Sumiyoshi¹,

Yamai²,

Tanaka³

et al. 2018

HETEROCYCLES

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-Using a novel tandem reduction-cyclization, we synthesized t-butyl 3-alkyloxindole-3-carboxylates from the di-t-butyl 2-alkyl-2-(2-nitrophenyl)-malonate. Introduction of an α-substituent to the di-t-butyl 2-(2-nitrophenyl)-malonates and addition of acid promoted reactivity.This methodology was successfully applied to gram-scale-synthesis of the t-butyl 3-methyloxindole-3-carboxylate 1 and 3-hydroxymethyl-3-methyloxindole 2 without silica gel column chromatography.

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Enantioselective Desymmetrization of Curcumins with 3‐Olefinic Oxindoles for the Synthesis of Spirocyclohexanoneoxindoles

et al. 2023

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An enantioselective desymmetrization of curcumins with 3‐olefinic oxindoles involving a cascade double‐Michael addition strategy provides direct access to spirocyclohexanone‐oxindoles with complete regio‐ and diastereoselectivities and excellent enantioselectivities, besides good to excellent yields. The products possess three contiguous chiral centers and multiple reactive functionalities. The observed selectivities were rationalized by transitions state energy calculations at B3LYP//6‐31g(d) level of DFT.

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Application of copper(II)-mediated radical cross-dehydrogenative coupling to prepare spirocyclic oxindoles and to a formal total synthesis of Satavaptan

Cited by 9 publications

References 29 publications

The applications of β‐keto amides for heterocycle synthesis

The applications of β‐keto amides for heterocycle synthesis

Synthesis of Substituted t-Butyl 3-Alkyloxindole-3-carboxylates from Di-t-butyl (2-Nitrophenyl)malonates

Enantioselective Desymmetrization of Curcumins with 3‐Olefinic Oxindoles for the Synthesis of Spirocyclohexanoneoxindoles

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