By Alan R. Katritzky
Chapters of this quantity take care of heavily similar tricyclic heteromatic platforms. The final accomplished evaluation 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 via Joule.The chemistry of 4-membered earrings containing one sulfur atom — the thietanes and their derivatives — is roofed through Ried and Heinz, who replace previous surveys that seemed approximately two decades ago.The bipyridines, of substantial commercial and theoretical curiosity, are comprehensively reviewed for the 1st time by means of Summers.Two chapters, facing 2H- and 4H- imidazoles through Sammes and the sequence editor, proceed and finish the sequence on nonaromatic azoles, which incorporated 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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Extra resources for Advances in Heterocyclic Chemistry, Vol. 35
Reagents: i, CH,=CHCOMe, benzene, 17,4 d; ii, DDQ, benzene, tl, 4 d. ~~ With but-3-en-2-one, 2-isopropenylbenzofuran (124, Scheme 31) affords the adducts 126 and 127 in a combined yield of 29%. When the crude product was dehydrogenated with 2,3-dichloro-5,6-dicyano1,Cbenzoquinone in boiling benzene, the aromatized product 128 (6%) was obtained. It was accompanied by the dicyanodibenzofuran 129, which was found to arise from the excess diene present in the reaction mixture. '30 2-Isopropenylbenzofuran (124), on reaction with dimethyl acetylenedicarboxylate, affords the dibenzofuran 130 (Scheme 32), the intermediate dihydrodibenzofuran undergoing dehydrogenation at the expense of the diene in as much as some 2-isopropylbenzofuran was isolated.
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The resultant adduct 96 on boiling with molar aqueous sodium hydroxide yields the tetrahydro-2-dibenzofuranone 97. ' 2 1 (97) (96) SCHEME 24 The 3(2H)-benzofuranone 98 undergoes Michael addition with (E)-pent3-en-2-one (100, Scheme 25) in the presence of sodium ethoxide to afford the adduct 101 as a mixture of two racemates. Cyclization to the 2-dibenzofuranone 102 can be induced by boiling with dilute aqueous sodium hydroxide under nitrogen or to the aromatized compound 103 in the presence of air.
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