One-pot protocol to synthesize N-(β-nitro)amides by tandem Henry/Ritter reaction

Abstract

A novel, efficient and atom economical one pot protocol for the synthesis of N-(β-nitro)amides has been described by combining the Henry reaction with the Ritter reaction.

Recent Applications of Ritter Reactions in Organic Syntheses

“…In the second step, the N ‐( β ‐nitro)amides 13 was synthesized through the Ritter reaction of produced alcohol as a product of henry reaction with nitriles 1 in the presence of TfOH in CH 2 Cl 2 (Scheme 39). [51] …”

Acid Catalyzed Multicomponent Reaction to Access Functionalized N‐Benzhydryl Amides: A Tandem Ritter Reaction

“…Further in a recent study, Prins‐Ritter reaction of cyclobutene alcohols produced complex diastereoselective tricyclic amide derivatives [24] . Henry‐Ritter reactions are reported to access one pot synthesis of N‐(β‐Nitro) amides from aldehyde, nitro compounds and nitriles [25] …”

“…[24] Henry-Ritter reactions are reported to access one pot synthesis of N-(β-Nitro) amides from aldehyde, nitro compounds and nitriles. [25] In continuation of our research efforts to explore CÀ H functionalisation reactions for the construction of CÀ C, [26,27] CÀ N [28,29] and CÀ O [30,31] bonds in open flask conditions, we aimed to investigate the one-pot multicomponent reaction for the synthesis of amides. Considering the importance of the complex amide products, we assumed that readily available and less expensive nitriles would be an excellent amidation tool in tandem Ritter reaction.…”

The serendipitous effect of KF in Ritter reaction: Photo-induced amino-alkylation of alkenes

“…As basic feedstock chemicals, simple alkenes have also been widely used as carbocation precursors in Ritter reaction ( Eren and Kusefoglu, 2005 ; Huang et al., 2012 ; Jiang and Studer, 2020 ; Nandy et al., 2020 ; Park et al., 2018 ; Shi et al., 2015 ; Subba Reddy et al., 2010 ; Welniak, 1996 ; Williams et al., 2017 ; Xu et al., 2017 ; Yang et al., 2018 ; Yasuda and Obora, 2015 ; Zhang et al., 2020 ). Of particular interest is the three-component Ritter reaction, which can efficiently incorporate two distinct functional groups onto the carbon-carbon double bonds in one-step ( Abe et al., 2010 , 2017 ; Ahmed et al., 2020 ; Ai et al., 2015 ; Bao et al., 2019 ; Chen et al., 2016 ; Feng et al., 2018 ; Liu and Klussmann, 2020 ; Qian et al., 2017 ; Zhu et al., 2017 ). Nowadays, photoredox catalysis ( Hopkinson et al., 2016 ; Marzo et al., 2018 ; Narayanam and Stephenson, 2011 ; Prier et al., 2013 ; Romero and Nicewicz, 2016 ; Shaw et al., 2016 ; Skubi et al., 2016 ; Tellis et al., 2016 ; Twilton et al., 2017 ; Xuan and Xiao, 2012 ; Yu et al., 2020 , 2021 ) for simultaneously constructing C−C and C−X bonds has become a new paradigm of alkene difunctionalizations ( Badir and Molander, 2020 ; Chen et al., 2018 ; Koike and Akita, 2016 ; Lipp et al., 2021 ; Protti et al., 2016 ; Yin et al., 2020 ; Zhu et al., 2020 ).…”