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J Med Chem Paper with DOB-like phenethylamines

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Rhodium:
Oh, great! Do you know if the -SCN, -OCN, -N3 or other pseudohalogenide derivatives has been made in the open literature?

megamole:
Rh,

As far as I can tell, not azido-, cyanato, or thiocyanato-2,5-dialkoxyphenethylamines exist of any kind. In fact, only a handful of phenethylamines bearing cyanates and thiocyanates have been synthesized, and none of them bear either of these groups on the 4-position.

There have, however, been a fiar number of interesting looking 4-azidophenethylamines. One in particular is 4-azido-alpha,alpha-dimethylphenethylamine (J. Biol. Chem.  (1981),  256(22),  11944-50.)

Rhodium:
These compounds are suitable for the preparation of the compounds in Post 228277 (slappy: "Re: J Med Chem Paper  with DOB-like phenethylamine", Methods Discourse)

Synthesis of Dihydrobenzofurans from Phenolic Mannich Bases and their Quaternized Derivatives
By Artur Blade-Font and Teodoro de Mas Rocabayera
J. Chem. Soc. Perkin Trans. 1. 841-848 (1982) (https://www.thevespiary.org/rhodium/Rhodium/pdf/dihydrobenzofurans.mannich.pdf)

Abstract
Reaction of dimethylsulphoxonium methylide with quaternized derivatives of phenolic Mannich bases, and in certain cases with the bases themselves, constitutes a useful synthesis of dihydrobenzofurans. On the other hand treatment of those same quaternized derivatives with diazomethane may be a useful alternative procedure for the preparation of coumarans with base-sensitive groups.

demorol:
Here is a complete article mentioned by Megamole in Post 229163 (megamole: "Re: J Med Chem Paper  with DOB-like phenethylamine", Methods Discourse). I hope you'll enjoy it.

Photoaffinity Labeling of the beta-Adrenergic Receptor
Thomas N. Lavin, Sarah L. Heald, Peter W. Jeffs, Robert G. L. Shorr, Robert J. Lefkowitz, and Marc G. Caron
Journal of Biological Chemistry, Vol. 256 (22), 11944-11950 (1981)

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