[MAFII]

I am not a student looking for an answer.  I am actually investigating a reaction and while looking at old papers, I came across this reaction:

http://pubs.acs.org/cgi-bin/archive.cgi/joceah/1953/18/i11/pdf/jo50017a013.pdf

sorry, I made a chemdraw picture, but I don't know how to add it onto this server?  However, the first reaction's mechanism is not 100% clear to me, can anybody help.

Thank you,

-M.

[Yarr]

In order to view your link one must have an account on that site. Since I don't have, could you describe the reaction?

[agrobert]

This link should be freely available

http://pubs.acs.org/cgi-bin/abstract.cgi/joceah/1953/18/i11/f-pdf/f_jo50017a013.pdf?sessid=6006l3

I'm still working out the mechanism, I don't understand the ketone addition because conditions do not appear favorable

[Rico]

I've attached a jpeg-file with a reasonable mechanism for the reaction in the link posted by agrobert.
The mechanism consists of an amide-formation, a conjugate addition, an aldol-type reaction (nucleophilic attack on the ketone), elimination of hydroxide ion, cyclization and in the end a decarboxylation. Some of the steps may occur in a different order.

I hope this is what you are looking for.

[Fry]

Why wouldnt the carboxylic acid protonate the last OH to give the iminium ion? And continue from there with the phenol attacking the imine?

[Rico]

I see your point, i did not think of that. That is probably a more reasonable mechanism.

[Fry]

Ah, okay I just thought there was something I was missing 

[MAFII]

I've attached a jpeg-file with a reasonable mechanism for the reaction in the link posted by agrobert.
The mechanism consists of an amide-formation, a conjugate addition, an aldol-type reaction (nucleophilic attack on the ketone), elimination of hydroxide ion, cyclization and in the end a decarboxylation. Some of the steps may occur in a different order.

I hope this is what you are looking for.

Thanks a lot, that looks very reasonable.  I wouldn't have guessed that there would be that great of a driving force for the conjugate addition.