Domino Sequence of Ketimization and Electrophilic Amination for an Inverse Aza Intramolecular Morita–Baylis–Hillman Adduct DOI

Mansingh Bairwa,

Rakesh Kumar Verma,

Kishor Chandra Bharadwaj

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 3, 2024

Morita-Baylis-Hillman (MBH) reaction, typically catalyzed by a Lewis base, is popular and useful method for C-C bond formation. Unfortunately, it limited slow reaction rate has sensitivity toward steric electronic parameters. Despite tremendous efforts, the versatility of keeps quest open new mechanistic catalytic pathways. Here, we have reported Bro̷nsted acid-catalyzed, electrophilic amination (Umpolung imine) as an inverse Aza Intramolecular MBH adduct in form 2-acylindole. Umpolung imine with nitrogen acting center been achieved. Interestingly, was also shown to occur under catalyst-free conditions also. The expected products ketimine formation, 6π electrocyclization, or quinoline formation were least/not observed. A large number examples demonstrated strength. β-aryl-substituted acrylate acrylamide (cinnamates cinnamides), which are extremely sluggish conventional chemistry, highlights developed methodology. annulated product exhibited keto-enol tautomerism, proven

Язык: Английский

Domino Sequence of Ketimization and Electrophilic Amination for an Inverse Aza Intramolecular Morita–Baylis–Hillman Adduct DOI

Mansingh Bairwa,

Rakesh Kumar Verma,

Kishor Chandra Bharadwaj

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 3, 2024

Morita-Baylis-Hillman (MBH) reaction, typically catalyzed by a Lewis base, is popular and useful method for C-C bond formation. Unfortunately, it limited slow reaction rate has sensitivity toward steric electronic parameters. Despite tremendous efforts, the versatility of keeps quest open new mechanistic catalytic pathways. Here, we have reported Bro̷nsted acid-catalyzed, electrophilic amination (Umpolung imine) as an inverse Aza Intramolecular MBH adduct in form 2-acylindole. Umpolung imine with nitrogen acting center been achieved. Interestingly, was also shown to occur under catalyst-free conditions also. The expected products ketimine formation, 6π electrocyclization, or quinoline formation were least/not observed. A large number examples demonstrated strength. β-aryl-substituted acrylate acrylamide (cinnamates cinnamides), which are extremely sluggish conventional chemistry, highlights developed methodology. annulated product exhibited keto-enol tautomerism, proven

Язык: Английский

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