166451-13-4

Upstream product

• 166451-12-3 (S)-(2-azidophenyl)(2-(hydroxymethyl)pyrrolidin-1-yl)methanone 
• 72435-94-0 (S)-N-(2-nitrobenzyl)pyrrolidine-2-carboxaldehyde 
• 142114-82-7 methyl (2S)-N-(2-azidobenzoyl)pyrrolidine-2-carboxylate 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 147-85-3 L-proline 
• 31162-13-7 2-azidobenzoic acid 
• 610-14-0 2-nitrobenzyl chloride 

Downstream Products

• 72435-89-3 (11aS)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one 

Relevant academic research and scientific papers

Intramolecular azide to alkene cycloadditions for the construction of pyrrolobenzodiazepines and azetidino-benzodiazepines

The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrr

Intramolecular 1,3-dipolar cycloaddition as a route to triazolobenzodiazepines and pyrrolobenzodiazepines

Intramolecular 1,3-dipolar cycloaddition between an alkyne and an azide leads to a series of 1,2,3-triazolo-fused 1,4-benzodiazepines, 1,2,5-benzothiadiazepines, pyrrolobenzodiazepines and pyrrolobenzothiadiazepines (eight examples). The products are priv

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepines and their conjugates by azido reductive cyclization strategy as potential DNA-binding agents

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepines via azido reductive cyclization process employing FeCl3-NaI reagent system. This methodology has been extended for the preparation of new nicotinamido- pyrrolobenzodiazepine hybrids linked through piperazino-alkane-oxy spacers that exhibit good DNA binding affinity.

Synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines by employing polymer-supported reagents: Preparation of DC-81

Polymer-supported reagents have been utilized for the generation of combinatorial library of substituted pyrrolo[2,1-c][1,4]benzodiazepine derivatives that provides a clean and efficient preparation and does not require conventional purification techniques like chromatography. This methodology involves intra molecular aza-Wittig reaction and has been extended for the synthesis of the natural product DC-81 in good overall yields.

Microwave enhanced reduction of nitro and azido arenes to N-arylformamides employing Zn-HCOONH4: Synthesis of 4(3H)-quinazolinones and pyrrolo[2,1-c][1,4]benzodiazepines

Microwave mediated reduction of nitro and azido arenes to N-arylformamides using Zn-HCOONH4 is described. In the absence of microwave conditions, this methodology affords amines. This protocol has been extended to the synthesis of pyrrolo[2,1-c][1,4]benzodiazepines and 4(3H)-quinazolinones.

Simple and facile reduction of azides to amines: Synthesis of DNA interactive pyrrolo[2,1-c][1,4]benzodiazepines

The reduction of aromatic azido compounds to the corresponding amines with hydriodic acid has been investigated and found to result in high yields. This reductive methodology which proceeds under non refluxing condition has been extended for the synthesis of DNA-interactive pyrrolo[2,1-c][1,4] benzodiazepine antibiotics.

An efficient reduction of azides to amines: Synthesis of DNA interactive pyrrolo[2, 1-c][1,4]benzodiazepines

Reaction of a variety of azido compounds with FeSO4·7H2O/NH3 results in quantitative yields of the corresponding amino compounds. This reductive methodology has been extended towards the synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics. (C) 2000 Elsevier Science Ltd.

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepines via reductive cyclization of ω-Azido carbonyl compounds by TMSI: An efficient preparation of antibiotic DC-81 and its dimers

ω-Azido carbonyl compounds on reaction with trimethylsilyl iodide (in situ prepared from TMSCI/NaI) led to the formation of diazepine imines in good yields under mild conditions. This methodology has been applied to the parent unsubstituted pyrrolobenzodiazepine, the natural product DC-81 and its dimers. (C) 2000 Elsevier Science Ltd.

A new methodology for the reductive cyclization of ω-azido carbonyl compounds mediated by tetrathiomolybdate: Application to an efficient synthesis of pyrrolo[2,1-c][1,4]benzodiazepines

The ω-azido carbonyl compounds on treatment with tetrathiomolybdate, 1 led to the formation of 5, 6 and 7 membered cyclic imines in very good yields under mild conditions. This method is applied successfully to a new efficient synthesis of 1,4-benzodiazap

The Synthesis of Functionalized Pyrrolo-[2,1-c][1,4]-Benzodiazepines

Two concise and high yielding routes to the antitumour antibiotic pyrrolo-[2,1-c][1,4]-benzodiazepine ring system are described. Thus, condensation of prolinol with 2-azidobenzoylchloride gives the tertiary amide (3). Oxidation to the aldehyde (4) followe