Author Topic: 2-Amino-5-substituted oxazolines and intermediates  (Read 727 times)

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Vitus_Verdegast

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2-Amino-5-substituted oxazolines and intermediates
« on: September 30, 2003, 01:20:00 PM »

2-Amino-5-substituted oxazolines and intermediates as potential anorectants.

Freiter, Edward R.; Abdallah, Abdulmunien H.; Strycker, Stanley J.

Journal of Medicinal Chemistry 16(5), 510-12 (1973)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/2-amino-5-arylthiomethyloxazolines.pdf)
CAN 79:61392, AN 1973:461392

Abstract

2-Amino-5-arylthiomethyl-2-oxazolines and their intermediates 1-amino-3-arylthio-2-propanols showed significant anorectant activity but were less active than d-amphetamine.  The most active compd. in the series was 2-amino-5-(phenylthiomethyl)-2-oxazoline (I) [41136-03-2], which at 46 mg/kg orally decreased food intake by mice by 62% in the 1st hr after administration.  To synthesize I, thiophenol [108-98-5] was reacted with epichlorohydrin [106-89-8] in the presence of NaOH, and the resulting epoxide was reacted with NH3 to yield 1-amino-3-phenylthio-2-propanol [35550-43-7], which was reacted the CNBr and cyclized to I.


Rhodium

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Just for TFSE-Technical Reasons...
« Reply #1 on: September 30, 2003, 03:47:00 PM »
I uploaded the article in PDF format to my page and linked it from whitin your post, so that we have both the citation/abstract and the link in the same post  ;)