One-pot three component α-aminoalkylation of conjugated nitroalkenes and nitrodienes

Rajesh, Kunjanpillai; Shanbhag, Pramod; Raghavendra, M.; Bhardwaj, Pallavi; Namboothiri, Irishi N. N.

doi:10.1016/j.tetlet.2009.12.015

Cited by 11 publications

(8 citation statements)

References 56 publications

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“…The aminoalkylation of nitroalkenes and nitrodienes was successfully performed in one pot as well by generating the imines in situ from aldehydes and secondary amines under imidazole-TFA conditions (Scheme 3). 25 The MBH-reaction of nitroalkenes 6 with azodicarboxylates (DEAD and DIAD) was particularly important as it established the C-N bond under mild reaction conditions to afford hydrazinonitroalkenes 15 (Scheme 3). 26 We achieved this using imidazole in THF or DMAP in acetonitrile in excellent yields.…”

Section: Methodsmentioning

confidence: 99%

α-Functionalization of Nitroalkenes and Its Applications in Organic Synthesis

Nair

Kumar

Namboothiri

2016

Synlett

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The applications of Morita-Baylis-Hillman (MBH) and Rauhut-Currier (RC) adducts of nitroalkenes in the synthesis of various carbo-and heterocycles are summarized in this review. In recent years, the MBH adducts and their derivatives such as acetates and bromides have served as efficient synthons for the synthesis of bioactive compounds including natural products. The close proximity of various functional groups makes the MBH and RC adducts extremely valuable substrates in multicomponent and cascade reactions, including annulations, organocatalysis, and kinetic resolution, to name a few.

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Section: Methodsmentioning

confidence: 99%

α-Functionalization of Nitroalkenes and Its Applications in Organic Synthesis

Nair

Kumar

Namboothiri

2016

Synlett

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“…[ 7‐8 ] On the other hand, the reaction of activated functionalized dienes with imines or iminium salts under the Morita‐Baylis‐ Hillman (MBH) conditions is another promising approach to functionalized dienyl allylic amines. [ 9‐12 ] However, the poor E / Z selectivity observed in most of these reactions restricted the practicality of these reactions. Therefore, it is highly desirable to explore a new and efficient catalytic reaction to prepare functionalized dienyl allylic amines.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Palladium‐Catalyzed Aminomethylation of Nitrodienes and Dienones via Double C—N Bond Activation

Bao-jia

Zhang

et al. 2021

Chin. J. Chem.

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Main observation and conclusion A new strategy for the generation of the active Pd‐alkyl species from aminal via C—N bond activation has been established, in which the formation of zwitterionic intermediate through aza‐Michael addition of aminal to nitrodienes or dienones is identified as a key step for the activation of the C—N bond. The efficient strategy has enabled a new palladium‐catalyzed α‐aminomethylation of nitrodienes and dienones via double C—N bond activation. The scope and versatility of the reaction were demonstrated and a broad range of substrates bearing electron‐donating and ‐withdrawing groups on the aromatic rings were all compatible with this reaction to furnish the desired α‐aminomethylated products in moderate to good yields with excellent regioselectivities and E/Z selectivities.

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“…Thus facile aminoalkylation at the β-position of nitroalkenes 7 possess-ing aryl, heteroaryl, and alkyl substituents at the β-position as well as δ-substituted nitrobutadienes 12 could be achieved by treating them with formaldehyde 8 and a secondary amine 25 in the presence of imidazole as catalyst and trifluoroacetic acid as co-catalyst (Scheme 9). [20] The scope of this reaction was investigated by using different cyclic secondary amines such as morpholine, piperidine and thiomorpholine and in all the cases the products were obtained in moderate to high yields (48-83%) and excellent stereoselectivity. Multiple roles have been proposed for TFA as Brønsted acid in this reaction.…”

Section: Aminoalkylation/hydrazinationmentioning

confidence: 99%

Morita-Baylis-Hillman and Rauhut-Currier Reactions of Conjugated Nitroalkenes

Kaur

Namboothiri

2012

Chimia

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α-Functionalization of conjugated nitroalkenes and nitrodienes using various electrophiles in the presence of amine catalysts such as imidazole and DMAP and the synthetic applications of the products are reviewed. The electrophiles include formaldehyde, activated non-enolizable carbonyl compounds, activated imines, azodicarboxylates as well as activated alkenes such as nitroalkenes, MVK and acrylate. Reports on synthetic applications of the products, though only appearing in the last three years, highlight the potential of these multi-functional scaffolds to take part in diverse transformations such as Michael addition, cycloaddition and many cascade reactions leading to complex molecules including natural products.

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One-pot three component α-aminoalkylation of conjugated nitroalkenes and nitrodienes

Cited by 11 publications

References 56 publications

α-Functionalization of Nitroalkenes and Its Applications in Organic Synthesis

α-Functionalization of Nitroalkenes and Its Applications in Organic Synthesis

Palladium‐Catalyzed Aminomethylation of Nitrodienes and Dienones via Double C—N Bond Activation

Morita-Baylis-Hillman and Rauhut-Currier Reactions of Conjugated Nitroalkenes

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