-drone #342
Rhodium
Administrator posted 09-14-98 10:55 PM
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The only way I can think of right now would be by cyclizing the ortho-amino derivative of a 3-chloro propiophenone, but that's kinda obvious, as well as not that practical...
beagle boy
unregistered posted 09-15-98 11:40 AM
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Yep, best ways to THIQ's is through PEA's. Pictet-Gams synth constructs a 2-alkyl isoquinoline which could be reduced to THIQ: acetophenone + HONO goes to alpha-OH PEA. Reaction w/ acid halide gives the isoquinoline. And as long as you have that hydroxy PEA, why not dream up some aminorex deriv's.
Pomeranz-Fritsch synth reacts a benzaldehyde w/ aminoacetaldehyde diethyl acetal to give an imine. Imine is cyclized w/ H2SO4 to get quinoline. Yields variable, need e- releasing subst. on benzaldehyde.
Have any targets in mind?
Rho: That amino propriophenone above would give a quinoline rather than isoquinoline.