Rhodium‐Catalyzed Synthesis of 2,5‐Epoxybenzo[<i>f</i>][1,4]oxazepines by Tandem Reaction of 1‐Sulfonyl‐1,2,3‐triazoles and Salicylaldehydes

Shi, Yinping; Yu, Xia; Li, Chuan‐Ying

doi:10.1002/ejoc.201500912

Cited by 41 publications

(11 citation statements)

References 68 publications

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“…1,2,3-Triazoles 1a – d , k , 1e , 1f , 1g , 1h , and 1i , j and diazo compounds 17a , c are known compounds, which were prepared by the reported procedures.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 1-(2-Aminovinyl)indoles and 1,3′-Biindoles by Reaction of 2,2-Diaryl-Substituted 2H-Azirines with α-Imino Rh(II) Carbenoids

et al. 2019

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An effective and operationally simple method for the preparation of 1-(2-(sulfonamido)vinyl)indoles (SAV-indoles) by the Rh(II)-catalyzed reaction of 2,2-diaryl-2H-azirines with 1-sulfonyl-1,2,3-triazoles has been developed. This method enables the stereoselective synthesis of a variety of 1,2,3-trisubstituted indoles having a Z configuration of the (1-aryl-2-(sulfonamido)vinyl) substituent. The reaction mechanism, supported by DFT calculations, involves the formation of 1,4-diazahexa-1,3,5-trienes, which rapidly cyclize to 2,2-diaryl-1-sulfonyl-1,2-dihydropyrazines. These compounds can be isolated at an early stage of the reaction, but under prolonged heating they isomerize into 7aH-indolium ylides, followed by a barrierless 1,5-prototropic shift to SAV-indoles. The developed methodology was also applied to the preparation of 1,3′-biindoles from 2,2-diaryl-2H-azirines using 3-diazoindolin-2-imines instead of 1-sulfonyl-1,2,3-triazoles.

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“…1,2,3-Triazoles 1a – d , k , 1e , 1f , 1g , 1h , and 1i , j and diazo compounds 17a , c are known compounds, which were prepared by the reported procedures.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 1-(2-Aminovinyl)indoles and 1,3′-Biindoles by Reaction of 2,2-Diaryl-Substituted 2H-Azirines with α-Imino Rh(II) Carbenoids

et al. 2019

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“…Control experiment by using chiral benzyl alcohol produced the α- ). [44] The reaction scope was demonstrated by varying valuable functional groups on both the substrates and found that electronic variation had minimal impact on the reaction efficiency. Additionally, o-hydroxyacetophenone was also converted to the corresponding 1,4-oxazepine in good yield.…”

Section: Oà H Nà H Insertionmentioning

confidence: 99%

Catalytic Insertion Reactions of α‐Imino Carbenoids

Pal

Volla

2021

The Chemical Record

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Over the past decade, α-imino carbenoids generated via transition metal (such as rhodium, nickel, copper, palladium, silver) catalyzed denitrogenative ring-opening of N-sulfonyl-1,2,3-triazoles have found an extensive account of applications in synthetic organic chemistry. Particularly, they have been widely utilized as a donor/acceptor carbene complex in a range of transformations leading to diverse nitrogen containing compounds and heterocycles. Along the same direction, 3-diazoindolin-2-imines were successfully applied as an alternative source of αimino carbenoid precursors for the development of a number of methodologies to access diverse indole derivatives. This review summarizes the insertion reactions of α-imino metal carbenes derived from N-sulfonyl-1,2,3-triazoles and 3-diazoindolin-2-imines.

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“…(Scheme 27). [40] The reaction scope was broad, asv arious triazoles and salicylaldehyde derivatives could participate in the reaction. Twop ossible mechanisms were proposed.…”

Section: Attack By Oxygen Atommentioning

confidence: 99%

“…In 2015, Li and co‐workers reported a unusual transformation whereby salicylaldehyde derivatives could also react with the N ‐sulfonyl‐1,2,3‐triazoles 1 to give heterocycles. (Scheme ) . The reaction scope was broad, as various triazoles and salicylaldehyde derivatives could participate in the reaction.…”

Section: Reactions Of N‐sulfonyl‐123‐triazolesmentioning

confidence: 99%

Recent Advances in the Synthesis of Heterocycles and Related Substances Based on α‐Imino Rhodium Carbene Complexes Derived from N‐Sulfonyl‐1,2,3‐triazoles

Jiang

Sun

Tang

et al. 2016

Chemistry A European J

206

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In recent years, α-imino rhodium carbene complexes derived by ring-opening of N-sulfonyl-1,2,3-triazoles have attracted much attention from organic chemists. Many transformations of these species have been reported that involve, in most cases, nucleophilic attack at the carbene center of the α-imino rhodium carbene, facilitating the synthesis of a wide range of novel and useful compounds, particularly heterocycles. This Minireview mainly focuses on advances in the transformation of N-sulfonyl-1,2,3-triazoles during the past two years.

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Rhodium‐Catalyzed Synthesis of 2,5‐Epoxybenzo[f][1,4]oxazepines by Tandem Reaction of 1‐Sulfonyl‐1,2,3‐triazoles and Salicylaldehydes

Cited by 41 publications

References 68 publications

Synthesis of 1-(2-Aminovinyl)indoles and 1,3′-Biindoles by Reaction of 2,2-Diaryl-Substituted 2H-Azirines with α-Imino Rh(II) Carbenoids

Synthesis of 1-(2-Aminovinyl)indoles and 1,3′-Biindoles by Reaction of 2,2-Diaryl-Substituted 2H-Azirines with α-Imino Rh(II) Carbenoids

Catalytic Insertion Reactions of α‐Imino Carbenoids

Recent Advances in the Synthesis of Heterocycles and Related Substances Based on α‐Imino Rhodium Carbene Complexes Derived from N‐Sulfonyl‐1,2,3‐triazoles

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