Showing papers on "Thiazepine published in 2001"

Synthesis of novel optically pure quinolyl-β-amino alcohol derivatives from 2-amino thiophenol and chiral α-acetylenic ketones and their IBX-mediated oxidative cleavage to N-Boc quinolyl carboxamides ☆

Abstract: A methodology directed toward the stereoselective synthesis of novel quinolyl glycines is presented. This strategy is based on the cyclocondensation reaction between 2-amino thiophenol 4 and chiral acetylenic ketones of the type 3 containing a latent α-amino acid functionality. The initially formed benzo[b][1,4]thiazepine derivatives 5, readily undergo sulphur extrusion in refluxing toluene to yield the corresponding 2,4-disubstituted quinolines 6. Subsequent oxazolidine ring opening followed by in situ re-protection of the amino group afforded the corresponding quinolyl-β-amino alcohols 8a–8f in enantiomerically pure form and good overall yields. The derivatives 8 are in principle suitable precursors for the synthesis of novel optically pure quinolyl glycines through oxidation of the alcohol side chain. However, these amino alcohol derivatives 8, did not afford the expected quinolyl glycines 10 using numerous oxidising agents and reaction conditions. Instead, by reacting 8 with the mild oxidising reagent IBX 11, an oxidative CC cleavage leading to the N-Boc quinolyl carboxamides 12 took place.

Process for the preparation of 11-amino-3-chloro-6,11-dihydro-5,5-dioxo-6-methyl-dibenzo[c,f][1,2]-thiazepine and application to the synthesis of tianeptine

Abstract: Synthesis of 11-amino-3-chloro-6,11-dihydro-5,5-dioxo-6-methyl dibenzo(c,f)(1,2)thiazepine (I) and its salts, from 3-chloro-6,11-dihydro-6-methyl-5,5,11-trioxo dibenzo(c,f)(1,2)thiazepine (III). Synthesis of 11-amino-3-chloro-6,11-dihydro-5,5-dioxo-6-methyl dibenzo(c,f)(1,2)thiazepine of formula (I) and its salts, from 3-chloro-6,11-dihydro-6-methyl-5,5,11-trioxo dibenzo(c,f)(1,2)thiazepine of formula (III): Independent claims are also included for the use of (I) to prepare tianeptine (II) and its salts.

Process for preparing 11-amino-3-chlorine-6, 11-dihydrogen-5, 5-dioxo-6-methyl-dibenzo [c,f][1,2] thiazine and application of synthetic tianeptine

Abstract: Synthesis of 11-amino-3-chloro-6,11-dihydro-5,5-dioxo-6-methyl dibenzo(c,f)(1,2)thiazepine (I) and its salts, from 3-chloro-6,11-dihydro-6-methyl-5,5,11-trioxo dibenzo(c,f)(1,2)thiazepine (III). Synthesis of 11-amino-3-chloro-6,11-dihydro-5,5-dioxo-6-methyl dibenzo(c,f)(1,2)thiazepine of formula (I) and its salts, from 3-chloro-6,11-dihydro-6-methyl-5,5,11-trioxo dibenzo(c,f)(1,2)thiazepine of formula (III): Independent claims are also included for the use of (I) to prepare tianeptine (II) and its salts.

The Reaction of Binucleophilic Reagents Containing 1,4-Nucleophilic Centers with Perfluoro-2-methylpent-2-ene and Perfluoro-5-azanon-4-ene.

Abstract: Reaction between perfluoro-2-methylpent-2-ene or perfluoro-5-azanon-4-ene and the compounds of H 2 NCH 2 CXYZH (Z=O, NH; X=H, CH 3 ; Y=H, CH 3 , C 2 H 5 ) type in the presence of triethylamine give 7-membered heterocycles with two and three heteroatoms. Reaction of ethylenediamine with perfluoro-2-methylpent-2-ene results in 9-fluoro-5,9-bis(pentafluoroethyl)-6,8,8-tris(trifluoromethyl)-1,4-diazabicyclo[5.2.0]nona-4,6-diene and with perfluoro-5-azanon-4-ene leads only to 2,4-bis(heptafluoro-propyl)-6,7-dihydro-1H[1.3.5]thiazepine. Reaction of ethylene glycol with perfluoro-2-methylpent-2-ene results in 2-fluoro-2,4-bis-(heptafluoropropyl)-6,7-dihydro-2H[1.5.3]dioxazepine. The routes of formation for these products have been discussed and the role of triethylamine in these reactions is elucidated.