foxy2 (Hive Addict)
05-14-01 14:20
No 194282
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This link has some very interesting synthetic routes illustrated for the truely revolutionary explorers.

How about vanillin to TMA-2 and TMA-2 analogs?
(3,4-dimethoxybenzaldehyde --> 2-bromo,3-methoxy,4-hydroxy benzaldehyde)

How about 7-substituted Indole derivatives, Shulgin never explored these!!
And an aromatic fluorinating example for Rhodium.

These are primarily based upon material derived from the "Handbook of Heterocyclic Chemistry" A. R. Katritzky, Pergamon Press, Oxford, 198. "The Handbook of Heterocyclic Chemistry Second Edition" (ISBN: 0-08-042988-2) will be published soon. For further information contact: Marie Bowler, The Boulevard, Langford Lane, Kidlington, Oxford OX5 1GB, UK. Email:

Do Your Part To Win The War
(Hive Bee)
09-15-01 05:58
No 213763
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I think we could come up with two more potential structures if one were to subsitute either mexamine or tryptamine in place of tyramine in step two of your proposed schematic.... I'd bet the effects resulting from the proposed SAR activity would be worth investigating.

What do ya think?

(Distinctive Doe)
09-16-01 00:04
No 213897
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I just meant that they brominated the 2 position of vanillin.  some bees would be interested in doing that

Do Your Part To Win The War
(Ubiquitous Precursor Medal Winner)
09-17-01 11:47
No 214286
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... that they brominated the 2 position of methylvanillin. That must somehow explain the bromination into that 2-slot. I know for sure plain vanilla vanillin, with its naked 4-hydroxyl showing, will brominate into the #5 position, with similarly high yields. I've wondered about this ever since you posted this pic elsewhere. But since I'm effectively without access to chem literature, I figured the only way I could find out, was to methylate (alkylate, preferably with an allyl or isopropyl group) some vanillin, and then watch where it brominates.

You need little teeny eyes, to see details like that. Like where a bromine atom sticks onto a benzene ring. If it's the methyl ether that switches the preferred ring bromination position from 5 to 2, a good guess is that other alkyl ethers might also perform this trick. Since I know nothing, I have to make a lot of guesses.

turning science fact into <<science fiction>>
(Chief Bee)
09-18-01 00:42
No 214505
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I agree with Halfapint, alkylating vanillin (with R-Br or R-I and K2CO3 in acetone) followed by bromination, and methoxylation of the bromine using methoxide in methanol with CuI as catalyst would give the desired 2,5-dimethoxy-4-alkoxy-benzaldehyde.