Advances in Heterocyclic Chemistry, Vol. 96 by Alan R. Katritzky

By Alan R. Katritzky

The definitive serial within the box — due to the fact 1960.* offers up to date fabric on a quick turning out to be and hugely topical topic quarter* includes the newest examine masking a wide selection of heterocyclic subject matters* Written by means of prime specialists and designed as a guide for college students and and educational researchers

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Thus, indolo benzazepine 36a, protected on the indole ring, and benzoxepine 36c are easily methylated on the benzazepine nitrogen (Scheme 79 (1991JHC379)). 2 (1993MI249)) and 7,12-dihydro-6H-[1]benzothiepino[5,4-b]indole (2006BMCL3233). O. Tymoshenko O O MeI, NaH, DMF HN X N X O 36a, c X = o-NO2C6H4CONH, Et2NCH2CH2NH2, DMF, rt, 2 h, 96%; Me O 384a X = o -NO2C6H4CONH, O Me N N H O 385 73%; 384b X = O, 73% Scheme 79 The reactivity of N-nucleophilic sites of other fused heteropines towards acylating agents is similar to pyrrolo-benzazepines described at the beginning of this chapter.

An alternative sequence starts with the addition of nitromethane to the C–N double bond on the thiadiazepine ring, nitro group reduction and manganese oxide oxidation of the intermediate dihydroimidazole derived from amine 342 and triethyl ortho formate. 4 Reduction The most general of this type of transformation is the reduction of lactam carbonyls on five- or seven-membered rings. Examples also include the reduction of C–C or C–N double bonds on the azepine ring. 1 (2001H1519)).

HCl Cy N 2. ArCHO 3. o -HSC6H4NH2 299 H N S Ar (35) 300 Two types of benzothiazepines with fused indole rings 301 and 302 (Figure 4) have been reported as products of a Fischer indole type synthesis (1993EJM659). 3-Arylthioindole-2-carboxylic acids 303, obtained from aryl disulfides and indole-2-carboxylic acids, afford tetracyclic 5H-indolo-[3,2-b][1,5]benzothiazepin6(7H)-ones 304 on treatment with EDC–DMAP (Scheme 65 (1998MI139)). 2H-Pyrrolo[3,4-b][1,5]benzothiazepine 307 can be obtained by thermal cyclization of pyrrole aminoester 308 (R ¼ Et) in the presence of 2-hydroxypyridine (Scheme 66 (1998SC2517, 2005FES385)).

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