91190-44-2

Upstream product

• 622-77-5 N-benzylcyanamide 
• 91190-60-2 2-(N-Benzylamino)-1,3-oxazole 
• 74-88-4 methyl iodide 

Downstream Products

• 91190-49-7 2-[2-(Benzyl-methyl-amino)-oxazole-5-carbonyl]-3,3-dimethyl-butyronitrile 
• 91190-57-7 (3aR,7R,7aR)-2-(Benzyl-methyl-amino)-7-tert-butyl-4-[1-cyano-2,2-dimethyl-prop-(E)-ylidene]-6-oxo-3a,6,7,7a-tetrahydro-4H-pyrano[4,3-d]oxazole-7-carbonitrile 
• 91237-29-5 (3aS,7R,7aS)-2-(Benzyl-methyl-amino)-7-tert-butyl-4-[1-cyano-2,2-dimethyl-prop-(E)-ylidene]-6-oxo-3a,6,7,7a-tetrahydro-4H-pyrano[4,3-d]oxazole-7-carbonitrile 
• 113470-79-4 Benzyl-methyl-((3aR,9aR)-5,6,7,8-tetrachloro-3a,9a-dihydro-1,4,9-trioxa-3-aza-cyclopenta[b]naphthalen-2-yl)-amine 
• 91190-55-5 1-[2-(Benzyl-methyl-amino)-oxazol-5-yl]-2,2-dichloro-ethanone 
• 91190-59-9 Dichloro-acetic acid 1-[2-(benzyl-methyl-amino)-oxazol-5-yl]-2,2-dichloro-vinyl ester 
• 91190-53-3 3-[2-(Benzyl-methyl-amino)-oxazol-5-yl]-2-chloro-3-oxo-propionitrile 
• 113203-24-0 Benzyl-methyl-((1S,2R,6S,7R)-1,7,8,9-tetrachloro-10,10-dimethoxy-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]deca-4,8-dien-4-yl)-amine 
• 113470-80-7 Benzyl-((1R,2R,6S,7S)-1,7,8,9,10,10-hexachloro-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]deca-4,8-dien-4-yl)-methyl-amine 
• 91190-51-1 1-[2-(Benzyl-methyl-amino)-oxazol-5-yl]-2,2-diphenyl-ethanone 
• 113470-81-8 Benzyl-methyl-((3aR,7aS)-4,5,6,7-tetrachloro-3a,7a-dihydro-benzooxazol-2-yl)-amine 

Relevant academic research and scientific papers

Selective Carbon-Carbon Bond Formation at the Oxazole Ring. Cycloadditions and Michael-Type Additions of Ketenes to 1,3-Oxazoles

1,3-Oxazole (1a) and 4-methyl-1,3-oxazole (1b) react with dichloroketene (DCK) affording the 2-(dichloroacetyl)oxazoles 3a and 3b, respectively, very likely via the corresponding N-acyloxazolium ylides as intermediates. 2-(N-Benzyl-N-methylamino)-1,3-oxazole (1c) and tert-butylcyanoketene (TBCK) give the 5-acyl derivative 4c and a mixture of the diastereomeric 2:1 cycloadducts 5 and 6 constituted by a δ-lactone ring condensed across the former C4-C5 bond of 1c.The 4-methyl derivative 1d affords the ketone 4d and the enol ester 7, whereas the 4,5-dimethyl derivative 1e undergoes the addition of 2 mol TBCK and ring fission producing a 2,5-dihydrofuran derivative 8.Other ketenes, namely diphenyl- (DPK), chlorocyano- (CCK), and dichloroketene (DCK), react with 1c and 1d to give the corresponding 5-acyl derivatives 4, and in the case of DCK only, also the enol ester 11.Plausible schemes accounting for the formation of products 4-11 involve as a common step, the initial attack of the ketene at C5 of the oxazole ring to give a zwitterion which undergoes different reactions depending on the substitution at C4 and C5 of the heterocycle.