74675-35-7Relevant academic research and scientific papers
A Ring Destruction Approach To Some Benzo-Fused Medium-Sized Heterocycles by Means of Cyanogen Bromide under Solvolytic Conditions. X-Ray Structure of a 1H-2,6-Benzoxazecine-6-Carbonitrile and a 2H-3,6-Benzoxazecine-6-Carbonitrile Derivative
Bremner, John B.,Raston, Colin L.,Rowbottom, Graham L.,White, Allan H.,Winzenberg, Kevin N.
, p. 893 - 912 (2007/10/02)
Reaction of the reduced pyrroloisoquinoline amine (1a) with cyanogen bromide in the presence of methanol gave the medium-ring cyanamide derivative 7,9,10-trimethoxy-2,3,4,5,6,7-hexahydro-1H-3-benzazonine-3-carbonitrile (2a).Analogous products were also obtained from reaction of the reduced 5H-oxazoloisoquinoline, 2H-benzoquinolizine, 2H,6H-oxazinoisoguinoline and oxazinoisoquinoline derivatives (1b-e), whereas the reduced 3H-oxazoloisoguinoline and 5H-oxazoloisoquioline derivatives (1f) and (8) gave 1-(2,4-dioxapentyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonitrile (5a) andN--N-methylcyanamide (9) respectively, the latter in low yield.The medium-sized heterocyclic derivatives (2f-h) were also obtained from cyanogen bromide-mediated water solvolysis reaction of (1a), (1c) and (1e).The cyanamides (2a-h), (5a) and (9) have been converted into the respective tertiary amine derivatives (3a-h), (5c) and (11), with concomitant reduction of the carbonyl group in the last case.The crystal and molecular structure of 1,10,11-trimethoxy-3,4,5,6,7,8-hexahydro-1H-2,6-benzoxazecine-6-carbonitrile (2d) and 1-hydroxy-10,11-dimethoxy-1,4,5,6,7,8-hexahydro-2H-3,6-benzoxazecine-6-carbonitrile (2h) have been determined by single-crystal X-ray methods.
