TY - JOUR
T1 - Ring-opening reactions of N-aryl-1,2,3,4-tetrahydroisoquinolines: Synthesis of novel isoquino[2,1-a][3,1]benzoxazine derivatives
AU - Stanforth, Stephen
PY - 2000/1/14
Y1 - 2000/1/14
N2 - The aldehydes 7e and 7h were prepared by treatment of the 1,2,3,4- tetrahydroisoquinolines 5e and 5h, respectively, with N-bromosuccinimide (NBS). Basic hydrolysis of compounds 7e and 7h gave the 4bH,6H-isoquino[2,1- a][3,1]benzoxazine derivatives 9 (R=H, OMe). Heterocycle 10 was obtained from the reaction of compound 5c with NBS and isolated as the ethyl derivative 11.
AB - The aldehydes 7e and 7h were prepared by treatment of the 1,2,3,4- tetrahydroisoquinolines 5e and 5h, respectively, with N-bromosuccinimide (NBS). Basic hydrolysis of compounds 7e and 7h gave the 4bH,6H-isoquino[2,1- a][3,1]benzoxazine derivatives 9 (R=H, OMe). Heterocycle 10 was obtained from the reaction of compound 5c with NBS and isolated as the ethyl derivative 11.
KW - Isoquino[2
KW - 1-a][3
KW - 1]benzoxazines
KW - ring-opening
KW - Tetrahydroisoquinolines
U2 - 10.1016/S0040-4020(99)01015-7
DO - 10.1016/S0040-4020(99)01015-7
M3 - Article
VL - 56
SP - 461
EP - 464
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 3
ER -