Thermal [2+2]-Cycloadditions of Diphenylketene with Aryl- and Hetaryl-Substituted Thioketones

Heimgartner, Heinz; Mlostoń, Grzegorz; Urbaniak, Katarzyna; Szychowska, Anna; Linden, Anthony

doi:10.3987/com-14-s(k)56

HETEROCYCLES

2015

DOI: 10.3987/com-14-s(k)56

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Thermal [2+2]-Cycloadditions of Diphenylketene with Aryl- and Hetaryl-Substituted Thioketones

Heinz Heimgartner¹,

Grzegorz Mlostoń²,

Katarzyna Urbaniak³

et al.

Abstract: -The reaction of diphenylketene (1) with aryl-and hetaryl-substituted thioketones (2) gave the corresponding 3,3,4,4-tetraarylthietan-2-ones (3) in good yields. Remarkably, the reactions with bis-hetaryl-substituted thioketones occurred significantly faster compared with those involving the bis-aryl-substituted thioketones. The structure of compound 3c has been established by X-ray crystallography.

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Cited by 10 publications

References 36 publications

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Brønsted Acid Catalyzed (3+2)‐Cycloaddition of Thioketones and Indole‐2‐Carbinols Toward Thiazolo[3,4‐a]indoles

Sachse

Schneider

2021

Adv Synth Catal

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Herein, we report a Brønsted acid catalyzed approach to access the yet unknown heterocyclic motif of thiazolo [3,4-a]indoles in a one-pot reaction under very mild conditions. A broad range of thiazolo[3,4-a]indoles was generated from indole-2-methanols and thioketones with 45-99% yield and good functional group tolerance. The practicality of the process and the synthetic potential of the products were demonstrated with an upscaling experiment and further transformations. Additional control experiments provided mechanistic insights into this cycloaddition.

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Brønsted Acid Catalyzed (3+2)‐Cycloaddition of Thioketones and Indole‐2‐Carbinols Toward Thiazolo[3,4‐a]indoles

Sachse

Schneider

2021

Adv Synth Catal

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Stereospezifische Reaktion von Donor‐Akzeptor‐Cyclopropanen mit Thioketonen: ein Zugang zu hoch substituierten Tetrahydrothiophenen

et al. 2017

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Lewis-acid-catalyzed reactions of 2-substituted cyclopropane 1,1-dicarboxylates with thioketones are described. Highly substituted tetrahydrothiophenes with two adjacent quaternary carbon atoms were obtained in a stereospecific manner under mild conditions and in high yield using AlCl3 as Lewis acid. Moreover, an intramolecular approach was successfully implemented to gain access to sulfur-bridged [n.2.1] bicyclic ring systems. Conversion of selenoketones, the heavier analogs, under similar conditions resulted in the formation of various tetrahydroselenophenes.

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Stereospecific Reactions of Donor–Acceptor Cyclopropanes with Thioketones: Access to Highly Substituted Tetrahydrothiophenes

et al. 2017

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Lewis-acid-catalyzed reactions of 2-substituted cyclopropane 1,1-dicarboxylates with thioketones are described. Highly substituted tetrahydrothiophenes with two adjacent quaternary carbon atoms were obtained in a stereospecific manner under mild conditions and in high yield when using AlCl as Lewis acid. Moreover, an intramolecular approach was successfully implemented to gain access to sulfur-bridged [n.2.1] bicyclic ring systems. Conversion of selenoketones, the heavier analogues, under similar conditions resulted in the formation of various tetrahydroselenophenes.

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Thermal [2+2]-Cycloadditions of Diphenylketene with Aryl- and Hetaryl-Substituted Thioketones

Cited by 10 publications

References 36 publications

Brønsted Acid Catalyzed (3+2)‐Cycloaddition of Thioketones and Indole‐2‐Carbinols Toward Thiazolo[3,4‐a]indoles

Brønsted Acid Catalyzed (3+2)‐Cycloaddition of Thioketones and Indole‐2‐Carbinols Toward Thiazolo[3,4‐a]indoles

Stereospezifische Reaktion von Donor‐Akzeptor‐Cyclopropanen mit Thioketonen: ein Zugang zu hoch substituierten Tetrahydrothiophenen

Stereospecific Reactions of Donor–Acceptor Cyclopropanes with Thioketones: Access to Highly Substituted Tetrahydrothiophenes

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