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

By Alan R. Katritzky

Chapters of this quantity care for heavily comparable tricyclic heteromatic platforms. The final entire evaluation of the dibenzofurans seemed in 1951; the topic is now up-to-date by way of Sargent and Stransky. Carbazoles have additionally now not been comprehensively reviewed lately; this has been performed during this quantity through Joule.The chemistry of 4-membered jewelry containing one sulfur atom — the thietanes and their derivatives — is roofed by way 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 through 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 conceal the literature up via 1982.

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1 28 J. D. Brewer, W. J. Davidson, J. A. Elix, and R. A. Leppik, Aust. I. Chmi. 24. I883 (1971). J. D. Brewer and J. A. Elix. A m . J . Chem. 25. 545 (1972). J. A. Elix and D. Tronson, Aust. J . Chem. 26, 1093 (1973). J. D. Brewer and J. A. Elix, Aust. J . C k e m 28, 1059 (1975). 1 3 ' J. D. Brewer and J. A. Elix, Aust. J . Chem. 28, 1083 (1975). ' j 2 B. Kamthong and A. Robertson, J . Chem. , 025. Y33 (1939). 12* 36 MELVYN v. STRANSKY [Sec. C NC CN ii I I Q--ffN Me Me (125) (89"/") (123) (80'::) SCHEME 30.

Tagaki, Bull. Cheni. Sac. Jpn. 39. 1961 (1966). Sec. ~' woMe MELVYN v. SARGENT AND PETER 0. STRANSKY 22 OMe Me0 \ OH I Me0 \ *-- J// Me (57) OH M OH e O Me HO Me HO w [Sec. B O M e OMe (58) OH Me Me has attempted to rationalize the reluctance of o-dihydroxyphenyl groups to participate in acid-catalyzed aromatic nucleophilic substitution in terms of molecular orbital calculations. Steric effects are sometimes important in determining the direction of cyclization of 2,2'-biphenyldiols. '' On prolonged treatment with boiling hydrobromic acid, however, the biphenyldiol 58 yielded the dibenzofuran 59, isolated as its tetra-0-methyl ether, as the major product and none of the alternative symmetrical isomer 60.

Tolstaya, Izu. Akud. Nauk SSSR, Otd. Khim. Nauk, 647 (1959) [ C A 53, 21796 (1959)l Sec. B] 27 DIBENZOFURANS 4. 64*'l o 5. By Ullmann-Type Synthesis Baker and co-workers" observed during the synthesis of the biphenyl 74 (Scheme 19) from the iodo compound 73 by the Ullmann reaction at 230°C with copper bronze in nitrobenzeiie that the dibenzofuran 75 (1%) M e o Me0 ~ ~ Br rM e 0 m Br M- -O e + Me Me0 Me0 OMe (73) (74) c1 \ / \ ,/ OMe (75) CI (78) C1 (79) SCHEME 19 Puskas, E. K. Fields, and E. M.

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