385446-23-1

Upstream product

• 6373-46-2 p-benzyloxyaniline 
• 1145-76-2 benzyl 4-nitrophenyl ether 
• 100-51-6 benzyl alcohol 
• 94040-95-6 1-azido-4-(benzyloxy)benzene 
• 6554-98-9 trans-4-Hydroxystilbene 
• 100-52-7 benzaldehyde 

Downstream Products

• 1221717-79-8 C₂₆H₂₇NO₃ 
• 39860-72-5 N-benzyl-4-(benzyloxy)aniline 

Relevant academic research and scientific papers

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.

Azetidinimines as a novel series of non-covalent broad-spectrum inhibitors of β-lactamases with submicromolar activities against carbapenemases KPC-2 (class A), NDM-1 (class B) and OXA-48 (class D)

The occurrence of resistances in Gram negative bacteria is steadily increasing to reach extremely worrying levels and one of the main causes of resistance is the massive spread of very efficient β-lactamases which render most β-lactam antibiotics useless. Herein, we report the development of a series of imino-analogues of β-lactams (namely azetidinimines) as efficient non-covalent inhibitors of β-lactamases. Despite the structural and mechanistic differences between serine-β-lactamases KPC-2 and OXA-48 and metallo-β-lactamase NDM-1, all three enzymes can be inhibited at a submicromolar level by compound 7dfm, which can also repotentiate imipenem against a resistant strain of Escherichia coli expressing NDM-1. We show that 7dfm can efficiently inhibit not only the three main clinically-relevant carbapenemases of Ambler classes A (KPC-2), B (NDM-1) and D (OXA-48) with Ki's below 0.3 μM, but also the cephalosporinase CMY-2 (class C, 86% inhibition at 10 μM). Our results pave the way for the development of a new structurally original family of non-covalent broad-spectrum inhibitors of β-lactamases.

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.

Mild and efficient PtO2-catalyzed one-pot reductive mono-N-alkylation of nitroarenes

(Chemical Equation Presented) A mild and efficient one-pot reductive monoalkylation of nitroarenes has been described using aldehydes as alkylating agents, molecular hydrogen as a reducing agent, and PtO2 as a catalyst in methanol. This methodology is found to be applicable for both aliphatic and aromatic aldehydes and for a wide variety of nitroarenes. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Commuications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.