155129-91-2

Usage

General Description

2H-Azirin-3-amine, N,2-dimethyl-N-phenyl-2-(phenylmethyl)- is a chemical compound with the molecular formula C15H18N2. It is also known as 3-Amino-2,2-dimethyl-N-phenyl-2-phenylethyl-2H-azirine and is a member of the aziridine family of compounds. It is used in organic synthesis and pharmaceutical research as a building block for the development of new drugs and compounds. This chemical is known for its potential biological activity and is of interest to researchers in the fields of medicinal chemistry and drug discovery. It is important to handle 2H-Azirin-3-amine, N,2-dimethyl-N-phenyl-2-(phenylmethyl)- with care as it may have toxic or hazardous properties.

Upstream product

• 155129-95-6 2-benzyl-N-methyl-N-phenylpropanamide 

Downstream Products

• 895533-39-8 2-{[2-(benzyloxy)acetyl]amino}-2,N-dimethyl-3,N-diphenylpropanamide 
• 895533-49-0 2-{[2-(benzyloxy)acetyl]amino}-2-methyl-3-phenylpropanoic acid 
• 895533-63-8 {[1-(dimethylcarbamoyl)-1-methyl-2-phenylethyl]carbamoyl}methyl 2-[(2-hydroxyacetyl)amino]-2-methyl-3-phenylpropanoate 
• 895533-68-3 {[1-({[1-(dimethylcarbamoyl)-1-methyl-2-phenylethyl]carbamoyl}methoxycarbonyl)-1-methyl-2-phenylethyl]carbamoyl}methyl 2-[(2-hydroxyacetyl)amino]-2-methyl-3-phenylpropanoate 

Relevant academic research and scientific papers

Azirine/oxindole ring enlargement via amidinium intermediates

A novel general method for the synthesis of oxindoles, namely the 'azirine/oxindole ring enlargement via amidinium-intermediates' has been established: the reaction of 2H-azirin-3-amines 1 with BF3· OEt2 in THF solution at -78° leads

Diazo-Transfer Reaction with Diphenyl Phosphorazidate

Diphenyl phosphorazidate (DPPA) was used as the azide source in a one-pot synthesis of 2,2-disubstituted 3-amino-2H-azirines 1 (Scheme 1).The reaction with lithium enolates of amides of type 2, bearing two substituents at C(2), proceeded smoothly in THF at 0 degree C; keteniminium azides C and azidoenamines D are likely intermediates.Under analogous reaction conditions, DPPA and amides of type 3 with only one substituent at C(2) gave 2-diazoamides 5 in fair-to-good yield (Scheme 2).The corresponding 2-diazo derivatives 6-8 were formed in low yield by treatment of the lithium enolates of N,N-dimethyl-2-phenylacetamide, methyl 2-phenylacetate, and benzyl phenyl ketone, respectively, with DPPA.Thermolysis of 2-diazo-N-methyl-N-phenylcarboxamides 5a and 5b yielded 3-subdtituted 1,3-dihydro-N-methyl-2H-indol-2-ones 9a and 9b, respectively (Scheme 3).The diazo compounds 5-8 reacted with 1,3-thiazole-5(4H)-thiones 10 and thiobenzophenone (13) to give 6-oxa-1,9-dithia-3-azaspironona-2,7-dienes 11 (Scheme 4) and thiirane-2-carboxylic acid derivatives 14 (Scheme 5), respectively.In analogy to previously described reactions, a mechanism via 1,3-dipolar cycloaddition, leading to 2,5-dihydro-1,3,4-thiadiazoles, and elimination of N2 to give the 'thiocarbonyl ylides' of type H or K is proposed.These dipolar intermediates with a conjugated C=O group then undergo either a 1,5-dipolar electrocyclization to give spiroheterocycles 11 or a 1,3-dipolar electrocyclization to thiiranes 14.