Synthesis and Reductive Reactions of 2,3‐Dioxo‐2,3‐dihydrobenzo[b]furo[2,3‐f]‐, ‐[2,3‐g]‐, and ‐[3,2‐e]indoles.

Abstract

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.

Recent trends in the chemistry of Sandmeyer reaction: a review

“…Later on, by using same reaction parameters Khoshtariya et al . in 2004 [ 98 ] and 2007 [ 99 ] synthesized 2,3-dioxo-2,3-dihydrobenzo[ b ]furoindoles and dioxodihydro-1 H -benzo[ b ]furoindole, respectively.

Scheme 47 3-Aminodibenzothiophene 198 , a starting precursor for the synthesis of benzo[ b ]thiophenoindoles

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Synthesis of new metoclopramide derivatives and in vitro evaluation of their human cholinesterases protection against Chlorpyrifos

“…Thus, the diazonium salt solution was prepared. Synthesis of compound I 15 The diazonium salt solution was brought to room temperature and heated in a water bath at 100 °C for (15 min) to allow the release of nitrogen gas. Distilled water (20 ml) was added to the mixture and the pH adjusted to 4.…”

Condensed tetracyclic systems with an isatin fragment in the molecule

“…Under the conditions of the Sandmeyer reaction with the procedures described in [4,5] the isonitrosoacetamidibenzofurans 3 and 4, obtained from 2-and 3-amidibenzofurans (1, 2), undergo cyclization with the formation of 1,2-dioxo-1,2-dihydro-1H-benzo [b]furo [3,2-e]indole (5), 2,3-dioxo-2,3-dihydro-1H-benzo[b]furo [2,3-f]indole (6), 2,3-dioxo-2,3-dihydro-1H-benzo [b]furo [3,2-f]indole (7), and 1,2-dioxo-1,2-dihydro-1H-benzo[b]furo [2,3-e]indole (8).…”

“…High antibacterial activity is exhibited, for example, by metisazone (marborane)-1-methylisatin 3-thiosemicarbazone [1-3]. Earlier we developed methods for the synthesis of the tetracyclic isomeric dioxodihydro-1H-benzo[b]furoindoles [4,5]. The present work was devoted to the synthesis of new tetracyclic condensed systems with linear and angular types of fusion containing isatin and benzofuran fragments.…”