[Shadow]

Is this synthesis of my reasonable: (instead of Pictet-Spengler it is Bischler-Napieralski Reaction)

I am not sure whether the azide will react in some steps. Help needed.

[Shadow]

Anyone familiar with azide chemistry? Any other suggestions for synthetic route?

[clarkstill]

I'd be a little concerned about your third structure: formula C4N4... There's a general rule that for azides to be safe the ratio C:N should be greater than 3:1.

[orgopete]

I'd also add the target looks very sensitive to aromatization. I'd bet that Pictet-Spangler would also aromatize the pyridine ring.

[Shadow]

Nice catch.

[Shadow]

Could anyone suggest another synthesis?

[Rutherford]

I'd also add the target looks very sensitive to aromatization. I'd bet that Pictet-Spangler would also aromatize the pyridine ring.

Bischler-Napieralski Reaction is used to synthesize dihydroisoquinolines, so there is no big threat of aromatization.

[critzz]

Would something like this work?



EDIT: Nevermind, I drew the lactone wrong. 

[kriggy]

not sure here but isnt paladium posioned by sulphur?