132488-55-2

Upstream product

• 64154-80-9 (2S,4R)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-hydroxy-pyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 253777-45-6 7-benzyloxy-6-methoxyisatoic anhydride 
• 706816-84-4 (2S,4R)-1-(2-Azido-4-benzyloxy-5-methoxy-benzoyl)-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester 
• 382137-65-7 methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate 
• 126588-03-2 N-<5-methoxy-4-(benzyloxy)-2-nitrobenzoyl>hydroxyproline ethyl ester 

Relevant academic research and scientific papers

Efficient reduction of aromatic nitro/azido groups on solid support employing indium: Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones

An efficient method for the reduction of aromatic nitro and azido compounds on solid support using indium/NH4Cl is described. This solid-phase reduction technique has been applied to the synthesis of pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione

One-pot microwave-assisted selective azido reduction/tandem cyclization in condensed and solid phase with nickel boride

An efficient and inexpensive method using microwave-assisted irradiation with Ni2B for the syntheses of aromatic amines, pyrrolobenzodiazepines as well as pyrroloquinazolinones was developed. This protocol was applied in the tandem resin-cleavage, azido reduction, and cyclization of compounds 3 and 5 that afforded substituted pyrrolo[2,1-c][1,4] benzodiazepines 4 and 6 in a one-pot manner. The microwave-assisted irradiation reactions enhanced yields with very short reaction times in contrast to the conventional thermal reactions. Georg Thieme Verlag Stuttgart.

Chemoselective aromatic azido reduction with concomitant aliphatic azide employing Al/Gd Triflates/Nal and ESI-MS mechanistic studies

Aluminium and gadolinium inflates catalyze the chemoselective reduction of aromatic azides to the corresponding amines in combination with sodium iodide. This mild chemoselective method has been applied to the synthesis of various aryl amines, C2azido-substituted pyrrolo[2,1-c]-[1,4]benzodiazepines, and fused[2,1b]quinazolinones by an intramolecular azido reduction tandem cyclization reaction. Interestingly, this methodology selectively reduces aryl azides with enhanced yields and proceeds in shorter reaction times than previous strategies. The mechanistic aspects have been investigated and the intermediates associated with this selective transformation have been intercepted and characterized by online monitoring of the reaction by ESI-MS.

An efficient selective reduction of aromatic azides to amines employing BF3·OEt2/NaI: Synthesis of pyrrolobenzodiazepines

A selective and facile method for the reduction of aromatic azides to amines by employing borontrifluoride diethyl etherate and sodium iodide. This methodology has been applied towards the preparation of biologically important imine-containing pyrrolobenzodiazepines and their dilactams through intramolecular reductive-cyclization process. In this protocol the reagent systems are amenable for the generation of solution-phase combinatorial synthesis. Georg Thieme Verlag Stuttgart.

Facile and efficient solid-phase synthesis of DNA-interactive pyrrolo[2,1-c] [1,4]benzodiazepines

The solid-phase synthesis of pyrrolo[2,1-c][1,4]benzodiazepines is described. Isatoic anhydrides attached to chloromethyl Wang resin are coupled with proline and the polymer-bound tricyclic compounds are reduced using very mild conditions, and successivel