Fused pyrrole derivatives R 0160 Synthesis and Reductive Reactions of 2,3-Dioxo-2,3-dihydrobenzo[b]furo[2,3-f]-, -[2,3-g]-, and -[3,2-e]indoles. -The reduction of the title compounds (IV), (IX), and (X), prepared by Sandmeyer reaction from the corresponding derivatives (III) and (VIII), is studied. The reduction with in situ prepared diborane leads to the benzo[b]furoindoles [cf. compounds (V), (XI), and (XIII)], while the use of LiAlH4 in Py as reducing agent allows to synthesize three novel hydroxybenzo[b]furoindoles [cf. derivatives (VI), (XII), and (XIV)]. -(KHOSHTARIYA, T. E.; MATNADZE, M. M.; MIRZIASHVILI, N. T.; KURKOVSKAYA, L. N.; SIKHARULIDZE, M. I.; DZHASHI, T. O.; Chem. Heterocycl.

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Preparation of N-Substituted 3H-Pyrrolo[2,3-c]phenothiazine 11,11-Dioxide.-A method for the alkylation of the pyrrole ring NH-group in (I) is demonstrated. Attempts to introduce an amino group into the side chain of the chloroacetyl substituted product (V) fail. -(KHOSHTARIYA, T. E.; MIRZIASHVILI, N. T.; SIKHARULIDZE, M. I.; KURKOVSKAYA, L. N.; SUVOROV, N. N.; PALAVANDISHVILI, G. A.; Chem. Heterocycl.

Fused pyrrole derivativesFused pyrrole derivatives R 0160 Novel Route for Obtaining Isomeric Benzo[b]thiophenoindoles. -The synthesis of title compounds such as (VI) and (VII) by reduction of the corresponding isatins (IV) and (V), obtained by cyclization of oxime (III) under Sandmeyer reaction conditions, is described. -(TSINTSADZE, T. G.; KHOSHTARIYA, T. E.; KURKOVSKAYA, L. N.; MIRZIASHVILI, N. T.; SIKHARULIDZE, M. I.; Chem. Heterocycl.

A preparative route is proposed for the synthesis of the novel heterocyclic systems 7-oxo-and 1,2,7-trioxo-1,2-dihydropyrano[3,2-e]indole using classical Fischer and Sandmeyer methods respectively. We have studied various conditions for cyclization of the starting coumarin 6-isonitrosoacetamide and the methyl or ethyl pyruvate 6-coumarinylhydrazones. The syn-and antiform ratio of the latter and the structure of all of the synthesized compounds were determined using spectroscopic data analysis.Keywords: 6-(isonitrosoacetamido)coumarin, 7-oxo-1,2-dihydropyrano[3,2-e]indole, Sandmeyer reaction, Fischer reaction, syn-Z-and anti-E-forms of pyruvate ester 6-coumarinylhydrazones, 1,2,7-trioxo-1,2-dihydropyrano[3,2-e]indole, cyclization.In continuing our study of condensed compounds containing a pyrrole ring [1-4] it was of interest to synthesize tricyclic systems which included indole and coumarin fragments. The interest in such a system is a result of the variety of the nature of the physiological activity of indole derivatives [5][6][7][8][9][10][11][12] and also the possibility of their use in the synthesis of alkaloids and alkaloid related substances.We have used classical Sandmeyer and Fischer reactions for the "addition" of a pyrrole ring to the bicyclic coumarin system (see Scheme).In the first case, the starting 6-aminocoumarin (1) was converted to the "isatin" 3 via the isonitrosoacetamide 2. In the second, the hydrazine hydrochloride 4 was obtained from the same amine via a diazonium salt and was then reacted with methyl or ethyl pyruvate to give the corresponding hydrazones 5a,b. Cyclization of the latter gave the target compounds 6a,b. _______ * Dedicated to the memory of a dear teacher, the prominent Russian science professor Nikolai Nikolaevich Suvorov. Founder of indole chemistry in Georgia. In love with, and a warm favourite of, Georgia. __________________________________________________________________________________________