Base and catalyst-free synthesis of nitrobenzodiazepines via a cascade N-nitroallylation-intramolecular aza-Michael addition involving o-phenylenediamines and nitroallylic acetates

Recent advances in the synthetic applications of Morita–Baylis–Hillman and Rauhut–Currier adducts of nitroalkenes

“…In 2019, our group also explored the reactivities of different nitrogen-based binucleophiles 59 , 60 and 61 with nitroallylic acetates 33 (Scheme 19). 29 When o -phenylenediamine 59 was treated with MBH acetates 33 , it underwent an allylic substitution followed by aza-Michael addition to form the corresponding nitrobenzodiazepines 62 in excellent yields and very good diastereomeric ratios. The highlight of this reaction was that it did not require any additional base or catalyst.…”

Visible Light‐Mediated Reactions of β‐Nitroalkenes

“…Nitroalkenes also found a variety of applications in organic synthesis due to their multiple reactive sites and reactivity pattern [19] . Nitroalkenes and their derivatives react in various ways such as Michael addition, cyclizations, denitrative couplings, Morita‐Baylis‐Hillman and Rauhut‐Currier reactions, etc [20–33] . The diverse reactivity, easy availability, and bench‐stable solid property make nitroalkene a unique motif in organic synthesis.…”

“…[19] Nitroalkenes and their derivatives react in various ways such as Michael addition, cyclizations, denitrative couplings, Morita-Baylis-Hillman and Rauhut-Currier reactions, etc. [20][21][22][23][24][25][26][27][28][29][30][31][32][33] The diverse reactivity, easy availability, and bench-stable solid property make nitroalkene a unique motif in organic synthesis.…”