Nucleophilic benzothiazepines

Pyrrolo[2,l-c][l,4]benzothiazepine 297 (R=Ph) has been prepared by an intramolecular nucleophilic displacement of acetyl derivative 296 (Scheme 64 (1992H51)). The same compound and its aryl (R = Ar (1992H51)) and carboethoxy or cyano (R = C(30Et or CN (1990H1291)) analogs can also be obtained by a Pummerer rearrangement-cyclization of sulfinyl precursor 298. 

Oxidation with 2,3-dichloro-5,6-dicyano-l,4-benzoquinone (DDQ) of the thiourea 51, derived from dopamine, gave the 1,3-benzothiazepine 53 in quantitative yield via a facile J-based nucleophilic intramolecular addition to the intermediate o-quinone 52 (Equation 9) <2005OBC2387>. 

The benzothiazepine ring 41 could be substituted at C-2 with propargylamine nucleophile, apparently without desulfurization, leading to an imidazole derivative 42 fused with a benzothiazepine (Equation 2) <1995EJM429, 1993FA665>. 

Oxidation with DDQ of the thiourea 183 derived from dopamine gave the 1,3-benzothiazepine 185 in quantitative yield via S-based nucleophilic intramolecular addition to the o-quinone 184 <05OBC2387>... 

One of the most common synthetic approaches to the construction of heterocyclic compounds involves the reaction of /3-keto esters with bifunctional nucleophiles. Thus a variety of reactions of (1) with different bifunctional heteronucleophiles, including hydrazine, substituted aminotriazoles, 2-aminopyridines, o-phenylenediamines, and o-aminothiophenol, lead to polynuclear condensed thieno compounds (e.g. 2-8) of potential medicinal interest featuring the pyrazolone, pyrimidinone, benzodiazepine, and benzothiazepine nuclei. Cannabinoid analogs can be prepared through cyclization of the condensation products of (1) with bifunctional oxygenated nucleophiles such as substituted resorcinols. ... 

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