Advances in Heterocyclic Chemistry, Vol. 35 by Alan R. Katritzky

By Alan R. Katritzky

Chapters of this quantity care for heavily similar tricyclic heteromatic platforms. The final entire evaluate of the dibenzofurans seemed in 1951; the topic is now up to date by way of Sargent and Stransky. Carbazoles have additionally no longer been comprehensively reviewed lately; this has been performed during this quantity by means of Joule.The chemistry of 4-membered earrings containing one sulfur atom — the thietanes and their derivatives — is roofed by means of Ried and Heinz, who replace past surveys that seemed approximately twenty years ago.The bipyridines, of substantial business and theoretical curiosity, are comprehensively reviewed for the 1st time by way of Summers.Two chapters, facing 2H- and 4H- imidazoles via Sammes and the sequence editor, proceed and finish the sequence on nonaromatic azoles, which integrated contributions on 2H- and 3H- pyrroles (in quantity 33) and on 3Н- and 4H- pyrazoles (in quantity 34).Most of the chapters during this quantity hide the literature up via 1982.

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The ion 165,by coupling with hydroquinone or reaction with benzoquinone, would lead to the other isolated products. The structures of the products have been verified by X-ray crystallography. -E. Hogberg. Tetrahedron 35, 535 (1979). -E. Berg, H. Erdtman. -E. Hogberg. B. Karlsson. -M. -C. , 1831 (1977). G . H. Erdtman, Proc. SOC. London, Ser A 143A. 177 (1934) [CA 28, 1337 (1934)l. 145 C. Brown, A. R. Forrester, and R. H. Thomson, Terruhedron 29, 3059 (1973). '43 44 MELVYN v. SARGENT AND PETER 0.

66 61 B. G. Pring and N. E. Stjernstrorn, Acta Chem. Scand. 22, 68 I (1968). N. P. Buu-Hoi, L. Petit, and D. C. Thang, J . Org. Chem. 29, 762 (1964). 69 E. Miiller, R. Mayer, B. Narr, A. Rieker, and K. Scheffler, Justus Liebigs Ann. Chem. 645, 25 (1961). 7 0 E. Pettersson and N. E. Stjernstrom, Ark. Kemi 21, 49 (1963). 7 1 B. G. Pring and N. E. Stjernstrom, A d a Chem. Scund. 22, 538 (1968). '* H. Erdtman, F. Haglid, and N. E. Stjernstrom, Acta Chetn. Scand. 15, 1761 (1961). 7 3 H. Musso, U. 1.

This type of reaction has been used in a synthesis of ruscodibenzofuran Reaction of 2,5-dimethyl-l,4-benzoquinone(185) with 3-methoxyphenol (186), followed by acetylation, gave the dibenzofuran 187 (Scheme 48). The derived phenol 188 was converted to the tetrazole derivative 189, which on hydrogenolysis gave the required intermediate 190 for the synthesis of ruscodibenzofuran (8). Treatment of veratrole (191) with excess of 2,5-dichloro- (192) or 2,6dichloro- 1,4-benzoquinone in 70% sulfuric acid yields dibenzofurans and other products.

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