ChemInform Abstract: Synthesis of 2,3‐Dihydrothieno(2,3‐b)quinolines and Thieno(2,3‐b)‐quinolines via an Unexpected Domino Aza‐MBH/Alkylation/Aldol Reaction.

Wei, Pei-Shun; Wang, Mengxue; D, Xu; Xie, Jian‐Hua

doi:10.1002/chin.201626035

Cited by 2 publications

(1 citation statement)

References 1 publication

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“…Similar elimination of two molecules of proline was reported during aza-Morita−Baylis−Hillman reactions. 24 The formation of α-configured C-glycoside rib-7 is a result of kinetic control of the retro-aza-Michael reaction. By thermodynamic control, the corresponding β-configured C-glycosides were obtained (long reaction times).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Matched/Mismatched Cases in Proline-Catalyzed Cascade Reactions with Carbohydrates: A Computational Insight into the Role of d- and l-Proline

Stier¹,

Chęciński²,

Witte

et al. 2018

J. Org. Chem.

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The cascade reactions of carbohydrates with methyl ketones in the presence of proline feature complex running reaction steps. By extensive quantum mechanical simulation, a coherent reaction mechanism was identified matching the experimental data. The present calculations indicate a Mannich reaction/proline hydrolysis/retro aza-Michael cascade to form an intermediate α,β-unsaturated ethyl ketone. This key precursor yields C-glycosides by a final intramolecular amine-catalyzed oxa-Michael addition. Additionally, the formation of this intermediate determines the rate and selectivity of the overall cascade reaction. Strongly matched and mismatched cases were observed when used with d- or l-proline. They are consistent with the calculated energy barriers of the corresponding transition states.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Matched/Mismatched Cases in Proline-Catalyzed Cascade Reactions with Carbohydrates: A Computational Insight into the Role of d- and l-Proline

Stier¹,

Chęciński²,

Witte

et al. 2018

J. Org. Chem.

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Simultaneous diversity-oriented synthesis of benzothiazoles and related diverse analogues by iodine-catalyzed intramolecular cyclization from identical substrates

Cui,

Wang,

Wang

et al. 2024

Aust. J. Chem.

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A facile oxidative cyclization of β-ketothioamides for the simultaneous formation of a compound library similar to natural product benzothiazole derivatives has been developed. The oxidative cyclization of β-ketothioamides resulted in the simultaneous formation of four classes of previously unknown benzothiazole derivatives. This chemistry’s versatility adds a valuable component to the methodology for obtaining benzothiazole derivatives.

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ChemInform Abstract: Synthesis of 2,3‐Dihydrothieno(2,3‐b)quinolines and Thieno(2,3‐b)‐quinolines via an Unexpected Domino Aza‐MBH/Alkylation/Aldol Reaction.

Cited by 2 publications

References 1 publication

Matched/Mismatched Cases in Proline-Catalyzed Cascade Reactions with Carbohydrates: A Computational Insight into the Role of d- and l-Proline

Matched/Mismatched Cases in Proline-Catalyzed Cascade Reactions with Carbohydrates: A Computational Insight into the Role of d- and l-Proline

Simultaneous diversity-oriented synthesis of benzothiazoles and related diverse analogues by iodine-catalyzed intramolecular cyclization from identical substrates

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