105089-64-3

Upstream product

• 2133-40-6 L-proline methyl ester monohydrochloride 
• 610-14-0 2-nitrobenzyl chloride 
• 552-16-9 ortho-nitrobenzoic acid 
• 18877-33-3 (S)-1-(2-nitrobenzoyl)pyrrolidine-2-carboxylic acid 
• 67-56-1 methanol 

Downstream Products

• 72435-94-0 (S)-N-(2-nitrobenzyl)pyrrolidine-2-carboxaldehyde 
• 105089-66-5 (2S)-N-(2-aminobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 105089-65-4 (2S)-N-(2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 176387-45-4 (S)-1-(2-Nitro-thiobenzoyl)-pyrrolidine-2-carbothioaldehyde 
• 72435-89-3 (11aS)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one 
• 24919-40-2 (S)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione 

Relevant academic research and scientific papers

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics: Oxidation of cyclic secondary amine with TPAP

A facile procedure for the preparation of the imine form of the pyrrolo(2,1-c][1,4]-benzodiazepine ring system by the oxidation of eyelid secondary amine with catalytic amounts of tetra-n-propylammonium perruthenate (TPAP) and N-methylmorpholine N-oxide (NMO) as a co-oxidant is described. This oxidative method is devoid of side-products and is thus a significant improvement over the Swern oxidation previously reported.

An efficient synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via reductive cyclization

A new and convenient one-pot synthesis of pyrrolo[2,1-c][1,4]benzodiazepine (PBD) ring system has been achieved by a reductive cyclization employing N,N-dimethylhydrazine and FeCl3.6H2O in good yields.

Chiral tertiary amine/L-proline cocatalyzed enantioselective Morita-Baylis-Hillman (MBH) reaction

Four types of chiral amines have been synthesized starting from readily available chiral sources. These chiral amines in combination with L-proline have been found to be efficient cocatalysts for the asymmetric Morita-Baylis-Hillman (MBH) reaction between methyl vinyl ketone (MVK) and aromatic aldehydes. The corresponding adducts were formed in reasonable chemical yields and with good enantioselectivities (up to 83 % ee). Moreover, parallel cocatalytic reactions with the two enantiomers of chiral amine 4 and L-proline revealed that it is the proline stereochemistry that determines the configuration of the newly formed chiral center. In addition, the existence of the free hydroxy group in amine 4a enhanced the enantioselectivity of the reaction. Based on these findings, a plausible mechanism for this cocatalytic MBH reaction has been proposed. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis of some new tertiary amines and their application as co-catalysts in combination with l-proline in enantioselective Baylis-Hillman reaction between o-nitrobenzaldehyde and methyl vinyl ketone

A chiral benzodiazepine derivative 1 was synthesized starting from o-nitrobenzoyl chloride and methyl l-prolinate hydrochloride. Diastereomeric (1R,2R,1′S)-(+)-2-[N-methyl-N-(α-phenylethyl)amino]cyclohexanol 3a and (1S,2S,1′S)-(+)-2-[N-methyl-N-(α-phenylethyl)amino]cyclohexanol 3b were synthesized starting from (S)-α-phenylethylamine and cyclohexene oxide via ring-opening, diastereomer separation and N-methylation. (S,S)-octahydrodipyrrolo[1,2-a:1′,2′-d]pyrazin 5 was synthesized from methyl l-prolinate. Chiral tertiary amines 1, 3a, 3b and 5 almost cannot catalyze the Baylis-Hillman reaction between o-nitrobenzaldehyde and methyl vinyl ketone (MVK). However, they functioned as efficient catalysts for this reaction in the presence of l-proline. The corresponding adducts were obtained in good yields with enantioselectivity of 83% ee, 81% ee, 51% ee and 66% ee, respectively.

Biphenyl derivatives and drug composition

A biphenyl derivative represented by the following general formula (1) and a pharmaceutically acceptable salt thereof: [In the formula (1), A represents a single bond, —CH2—, —CO—, —CS— or —SO2—; B represents a single bond or —CH2—; R1represents a hydrogen atom, —OH, —NR11R12(wherein R11and R12each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), —OCOCH3, or a halogen atom; R2represents a hydrogen atom or R1and R2form a group ═O together; R3represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; provided that in the formula, the absolute configuration of the position a may be either R or S]. The compound of the present invention has considerably high safety and efficacy and is useful as, in particular, a vasopressin receptor antagonist.

A new facile procedure for the preparation of pyrrolo[2,1-c][1,4]benzodiazepines : Synthesis of the antibiotic DC-81 and its thio analogue

An efficient synthesis of the imine form of the pyrrolo[2,1-c][1,4] benzodiazepine ring system based on a new reductive cyclization procedure is described. The naturally occuring antibiotic DC-81(5c) and its 5-thio analogue (7c) have also been synthesized to illustrate the usefulness of this methodology.

Catalytic reductive N-alkylation of anilines. Application to the synthesis of N-aryl aminoacid precursors

Different anilines have been monoalkylated by reductive alkylation using ketones and α-ketoesters as alkylating agents with good isolated yields. This provided access to aminoacid derivatives. Diastereoselective experiments were also performed.

A new route for the synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via oxidation of cycle secondary amine

The synthesis of the imine-containing pyrrolo[2,1-c][1,4]benzodiazepine DNA-binding antitumour antibiotics was achieved by a new method of oxidation of cyclic secondary amines which does not endanger the stereochemical integrity of the C-11a position.

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via azido reductive cyclization with HMDST

A new facile synthesis of pyrrolo[2,1-c][1,4]benzodiazepine (PBD) ring system has been achieved by reductive cyclization of the azide employing hexamethyldisilathiane (HMDST). The parent unsubstituted PBD and the natural product DC-81 have also been prepared in good overall yields.

A versatile and efficient synthesis of carbinolamine-containing pyrrolo[1,4]benzodiazepines via the cyclization of N-(2-aminobenzoy 1)pyrrolidine-2-carboxaldehyde diethyl thioacetals: Total synthesis of prothracarcin

A versatile and efficient synthesis of carbinolamine-containing pyrrolo[1,4]benzodiazepines (or the corresponding imine forms) of types 2, 7, and 8 is described that involves mercuric chloride mediated cyclization of the corresponding N-(2-aminobenzoyl)py