104751-08-8

Upstream product

• 29686-12-2 5-pentanolide 

Downstream Products

• 133910-69-7 (10bRS,13aRS)-1,2,3,5,6,13a-hexahydro-8,9-dimethoxy-13-phenylisoxazolo<6',5':3,4>pyrido<2,1-a>isoquinoline 
• 133930-03-7 4,5,6,7,8,9-hexahydro-11,12-dimethoxy-3-phenyl-7,7-dimethyl-4H-isoxazolo<4,5-g><3>benzazecinium iodide 
• 133910-74-4 4,5,6,7,8,9-hexahydro-11,12-dimethoxy-3-phenyl-7-(1-propyl)-4H-isoxazolo<4,5-g><3>benzazecine 

Relevant academic research and scientific papers

Synthesis of the 3-Azametacyclophane System by Oxidative Cleavage of a 3-Aza(1,7)naphthalenophane Derivative

Reaction of 10,11-dimethoxy-1,4,5,6-tetrahydro-7,9-ethano-3-benzazecine-3(2H)-carbonitrile (3) with ozone at -78 deg, followed by destruction of the ozonide with dimethyl sulfide, gave, in 82percent yield, 15-formyl-12,13-dimethoxy-8-oxo-4-azabicyclopentadeca-1(15),11,13-triene-4-carbonitrile (4), a representative of the new 3-azametacyclophane system.The precursor (3) was obtained by cyanogen bromide-induced eliminative ring destruction of 8,9-dimethoxy-2,3,5,6,10,11,11a,11b-octahydro-1H-benzopyridoquinoline (2) in 96percent yield.An attempt to make the analogous precursor for the 3-azametacyclophane system was unsuccessful due to a preferred nucleophilic attack by bromide ion.Reduction of (4) with sodium tetrahydroborate gave 8-hydroxy-15-(hydroxymethyl)-12,13-dimethoxy-4-azabicyclopentadeca-1(15),11,13-triene-4-carbonitrile (5) in 79percent yield.