TY - JOUR
T1 - Cyclisation Studies of 5–Substituted Arylalkyl – 1,2,3,4,5,6,7 – octahydroisoquinolines
AU - Dennison, Philip R.
AU - Gibson, Alan
AU - Gray, Alexander I.
AU - Patrick, Graham L.
PY - 1997
Y1 - 1997
N2 - Treatment of 2-methyl-5-(3-phenylpropyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline with 48% HBr results in isomerisation of the double bond and cyclisation at position-5 of the octahydroisoquinoline ring system to give a novel spiro structure. This is in contrast to the corresponding reaction with 5-[1-(2-phenethyl)]-1,2,3,4,5,6,7,8-octahydroisoquinoline where cyclisation takes place at position-6 of the octahydroisoquinoline ring system. Similar treatment of 5-benzyl-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline results in cyclisation at position-7 of the octahydroisoquinoline ring system to give a novel tetracyclic structure.
AB - Treatment of 2-methyl-5-(3-phenylpropyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline with 48% HBr results in isomerisation of the double bond and cyclisation at position-5 of the octahydroisoquinoline ring system to give a novel spiro structure. This is in contrast to the corresponding reaction with 5-[1-(2-phenethyl)]-1,2,3,4,5,6,7,8-octahydroisoquinoline where cyclisation takes place at position-6 of the octahydroisoquinoline ring system. Similar treatment of 5-benzyl-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline results in cyclisation at position-7 of the octahydroisoquinoline ring system to give a novel tetracyclic structure.
KW - 2-methyl-5-(3-phenylpropyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline
KW - Chemistry
U2 - 10.1039/A605296G
DO - 10.1039/A605296G
M3 - Article
SN - 2050-8255
VL - 5
SP - 721
EP - 727
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -