Biomedical Engineering Reference
In-Depth Information
SCHEME 7.6
Synthesis of spirohydantoins and spiro-2,5-diketopiperazines. Reagents and
conditions: (i) PhNCO, DCM, rt, 18 h; (ii)
t-
BuOK, THF, rt, 16 h; (iii) Fmoc-Ala-OH,
PyBOP/HOBt, rt, 4 h; (iv) 20% piperidine/DMF, rt, 20 min; (v) 5% AcOH, toluene, reflux, 4 h.
SCHEME 7.7
Synthesis of five various heterocycles derived from the dihydroisoquinoline
core skeleton. Reagents and conditions: (i) TfOH, DCM; (ii) 7-hydroxyisoquinoline, 2,6-
lutidine; (iii)
o
-bromobenzyl bromide; (iv) CH
2
=
CH-MgBr,
−
78
◦
C
→
0
◦
C; (v) NaBH
3
CN,
TFA/DCM; (vi) benzohydroximinoyl chloride; (vii) N
3
PO(OPh)
2
; (viii) DMAD; (ix)
p
-
fluorophenyl isocyanate.
