Fluoroalkyl amino compounds derivatives

The interesting P-amino nitro derivatives 24 (Scheme 6), potential precursors of a-fluoroalkyl p-diamino compounds, like 25, were also obtained from P-sulfinyl enamines 19 and nitromethane (15). Unfortunately, even in this case a low stereocontrol was obtained. 

Perfluoro(3-isothiocyanato-2-methyl-2-pentene) reacts with N-nucleophiles to produce a series of fluoroalkyl-substituted 6/f-l,3-thiazines <1997RJO720>. The acid-catalyzed cyclization of thioureas immobilized on Wang (X = O) or Rink resin (X = NH) provides a convenient route to a wide range of 2-amino-4/7-benzothiazine derivatives 212 (Scheme 23) <20000L3667>. The thioureas are obtained in four steps from 2-nitrocinnamic acids. A general synthesis of 2-alkylidene-4-imino-l,4-dihydrobenzo-l,3-thiazines 213-215 involves treatment of 2-isothiocyanato-benzonitrile with acidic methylene compounds under basic conditions <2003SL1503>. The ( )-isomers are the predominant isomers formed. 

Considerable activity continues with 0-glycosyl amino-acids. Two reports have appeared on 3-D-galactopyranosyl L-hydroxylysine derivatives,the first in connection with the development of assays for osteoporosis. An extensive range of related compounds W (with R = alkyl and fluoroalkyl), as well as related thioglycoside and 2-N-acetyl-2-deoxy compounds have been made as GalCer analogues for anti-HIV testing. ... 

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