The reaction of 1-tetralones with thallium trinitrate supported on clay: ring contraction vs alpha-oxidation

Ferraz, Helena M. C.; Silva, Luiz F.; Aguilar, Andrea M.; Vieira, Tiago O.

doi:10.1590/s0103-50532001000500012

Cited by 10 publications

(5 citation statements)

References 11 publications

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“…Under these conditions, a complex mixture of compounds was formed. 42 The thallium(III)-promoted oxidation of 1-tetralones was then investigated using the conditions previously described by Taylor et al 43 The reaction of a series of 1-tetralones with TTN supported on Montmorillonite K-10 clay led to products of ring contraction and/or α-oxidation, as illustrated by Scheme Singh et al described that the reaction of tetrahydro-4-quinolones with TTN gave the ring-contraction product together with a 3-methoxytetrahydro-4-quinolone as a minor product. A representative example is shown in Scheme 10.…”

Section: Scheme 8 Mechanism For the Thallium(iii)-mediated Ring Contrmentioning

confidence: 99%

Adventures in Ring-Contraction Reactions

Silva

2014

Synlett

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Nearly two decades of work on ring-contraction reactions is discussed in this account. We have developed several reliable protocols for the rearrangement of a number of different substrates using thallium(III) salts and, more recently, hypervalent iodine(III) reagents. A variety of ring systems, such as cyclopentanes, cis-and trans-hydrindanes, and indanes, can be obtained using these methods. Additionally, the stereoselective total syntheses of the sesquiterpenes (±)-, (-)-and (+)-mutisianthol and (+)-bakkenolide A, the indole alkaloid (±)-and (+)-trans-trikentrin A, and the potential drug (±)-indatraline have been achieved through a ring-contraction approach. 1 Introduction 2 Ring-Contraction Reactions Promoted by Thallium(III) 2.1 Thallium(III)-Mediated Ring Contraction of Cyclic Ketones 2.2 Thallium(III)-Mediated Ring Contraction of Cyclic Olefins 2.3 Thallium(III)-Mediated Ring Contraction of Homoallylic Alcohols 3 Ring-Contraction Reactions Promoted by Iodine(III) 4 Conclusion Key words: total synthesis, ring contractions, oxidative rearrangements, thallium(III), hypervalent iodine O TTN (1.1 equiv) CH 2 Cl 2 , r.t., 24 h CO 2 H 87% O TTN (1.5 equiv) CH 2 Cl 2 , r.t., 48 h CO 2 H 65%

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Section: Scheme 8 Mechanism For the Thallium(iii)-mediated Ring Contrmentioning

confidence: 99%

Adventures in Ring-Contraction Reactions

Silva

2014

Synlett

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“…of cycloalkanones (TTN in CH 2 Cl 2 ), a complex mixture of compounds was formed. 29 The thallium(III)-promoted oxidation of 1-tetralones was then investigated under the conditions previously described by McKillop, Taylor, and co-workers. 30 The reaction of a series of 1-tetralones with TTN supported on Montmorillonite K-10 clay led to products of ring contraction (methyl indan-1-carboxylates) and/or a-oxidation (2-methoxy-1-tetralones), in variable yields, as exemplified in Scheme 4.…”

Section: Biographical Sketchesmentioning

confidence: 99%

“…30 The reaction of a series of 1-tetralones with TTN supported on Montmorillonite K-10 clay led to products of ring contraction (methyl indan-1-carboxylates) and/or a-oxidation (2-methoxy-1-tetralones), in variable yields, as exemplified in Scheme 4. 29 However, the ring contraction of 4-quinolones could be performed with TTN in trimethyl orthoformate (TMOF), as discussed below (see Scheme 47). 31…”

Section: Biographical Sketchesmentioning

confidence: 99%

Thallium(III) in Organic Synthesis

Silva¹,

Carneiro²

2010

Synthesis

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This review article discusses the literature regarding thallium(III) compounds in synthetic organic chemistry published in the last decade, including several applications in the total synthesis of natural products. The reactions that received the most attention in this period were: i) the oxidative rearrangement of chalcones; ii) the ring contraction of cyclic alkenes; iii) the oxidation of homoallylic alcohols; iv) aromatic thallations; and v) oxidative couplings, including with phenols.

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“…A primeira abordagem consiste da reação de 1-tetralonas com TTN adsorvido em K-10 26 . Neste caso, a contração não ocorreu com alguns dos substratos estudados e, quando aconteceu, os rendimentos obtidos foram apenas moderados.…”

Section: Reações De Contração De Anelunclassified

Síntese de indanos: uma seleção de métodos gerais e eficientes

Ferraz¹,

Aguilar²,

Silva³

et al. 2005

Quím. Nova

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Recebido em 16/8/04; aceito em 1/10/04; publicado na web em 17/2/05 SYNTHESIS OF INDANS: A SELECTION OF GENERAL AND EFFICIENT METHODS. The indan ring system is present in several compounds with important pharmacological properties. In this account recent examples of selected methods (Friedel-Crafts acylation, cycloaddition reactions, ring contraction, cyclization and resolution) for the synthesis of indans are discussed.

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The reaction of 1-tetralones with thallium trinitrate supported on clay: ring contraction vs alpha-oxidation

Cited by 10 publications

References 11 publications

Adventures in Ring-Contraction Reactions

Adventures in Ring-Contraction Reactions

Thallium(III) in Organic Synthesis

Síntese de indanos: uma seleção de métodos gerais e eficientes

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