72435-89-3

Upstream product

• 72435-94-0 (S)-N-(2-nitrobenzyl)pyrrolidine-2-carboxaldehyde 
• 105089-66-5 (2S)-N-(2-aminobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 31162-13-7 2-azidobenzoic acid 
• 141874-26-2 N-Boc-(S)-proline chloride 
• 552-16-9 ortho-nitrobenzoic acid 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 
• 105089-87-0 benzyl (2S)-2-[di(ethylsulfanyl)methyl]tetrahydro-1H-1-pyrrolecarboxylate 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 1016557-03-1 C₁₄H₁₇N₅O₃ 
• 34897-85-3 o-azidobenzoyl chloride 
• 94811-92-4 (11aS)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo<2,1-c><1,4>benzodiazepine-5-one 
• 105089-65-4 (2S)-N-(2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 18877-33-3 (S)-1-(2-nitrobenzoyl)pyrrolidine-2-carboxylic acid 
• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 

Relevant academic research and scientific papers

Acceptorless dehydrogenative construction of CN and CC bonds through catalytic aza-Wittig and Wittig reactions in the presence of an air-stable ruthenium pincer complex

The construction of CN bonds was achieved by the dehydrogenative coupling of alcohol and azide via aza-Wittig type reaction. The reaction is catalyzed by an acridine-derived ruthenium pincer complex and does not use any oxidant. The present protocol offers a wide substrate scope, including aliphatic, aryl or heteroaryl alcohol/azides. This expeditious protocol was successfully applied to construct a CC bond directly from alcohol via dehydrogenative Wittig reaction. Furthermore, the synthesis of structurally important pyrrolo[1,4]benzodiazepine derivatives was also achieved by this methodology.

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.

A facile intramolecular azido/amido reductive cyclization approach: synthesis of pyrrolobenzodiazepines and their dimers

A new synthetic pathway has been developed for the preparation of imine-containing pyrrolo[2,1-c][1,4]benzodiazepines (PBDs) and their dimers. Selective reduction of aromatic azides as well as aliphatic amides in a single step leading to an intramolecular

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.

Conversion of amines to imines employing Polymer-Supported Sulfoxide (PSS) and Polymer-Supported Perruthenate (PSP): Synthesis of pyrrolo[2,1-c][1,4] benzodiazepines

An efficient method for the oxidation of secondary amines to the corresponding imines has been developed by employing polymer-supported reagents. This protocol has been extended for the generation of a combinatorial library of substituted pyrrolo[2,1-c][1,4]benzodiazepine derivatives and provides a rapid and clean preparation avoiding conventional purification techniques.

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 PROTECTED PYRROLOBENZODIAZEPINES

A method of synthesis of a N-10 protected PBD compound of formula (I) via an intermediate of formula (II) or formula (V).

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.

A new approach for the solid-phase synthesis of pyrrolo[2,1-c][1,4] benzodiazepines involving reductive cleavage

A methodology based on reductive cleavage followed by cyclization, for the solid-phase synthesis of pyrrolo[2,1-c][1,4]benzodiazepines employing DIBAL-H, is described.