Advances in Heterocyclic Chemistry by Alan R. Katritzky

By Alan R. Katritzky

(from preface)The 7th quantity of Advances in Heterocyclic Chemistry contains surveys of 4 teams of heterocyclic compounds; furans (P. Bosshard and nil. H. Eugster), dithiolium salts (H. Prinzbach and E. Futterer), 1,3,4-oxadiazoles (A. Hetzheim and okay. Mockel), and diquinolylme-thanes (G. Scheibe and E. Daltrozzo). extra chapters take care of functions of mass spectrometry to heterocycles (G. Spiteller), a space which has extended very quickly of past due, and the halogenation of heterocycles (J. J. Eisch). ultimately, a precis is given of experiences within the heterocyclic box, categorized via topic (A. R. Katritzky and S. M. Weeds), which it really is was hoping might be of information in literature surveys.Suggestions are welcomed for contributions to extra volumes; they need to be within the type of a brief synopsis.Thanks are a result of Editorial Board, the publishers, and the authors for his or her cooperation.

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62, 10575 (1965). 44 H. Quiniou and N. Lozac’h, Bull. SOC. Chim. France p. 1167 (1963). 45 E. Futterer, Dissertat,ion, Freiburg-im-Breisgau (1964). 46 A. Luttringhaus and W. Cleve, Ann. 575, 112 (1952). 478 F. Bauer, Chem. Ztg. 75, 3 (1951). 43E. 11. 2 Whereas “trithiones” (some of them a t least) were until recently obtainable only at great preparative cost, a number of simple and very productive syntheses have been developed in the past fewyears. 47b The oxidative elimination of the thione sulfur from the “trithiones ” has therefore become the most important method of synthesizing 1,2-dithiolium salts (Table 11).

88 28 JOHN J. EISCH [SEC. 4 2 I n acidic media not as yet studied kinetically, the candidate halogenating agents can only be surmised. A solution of molecular halogen in concentrated sulfuric acid with added silver sulfate appears to generate X-S04H as the active species. Likewise, in aqueous acid, hypohalous acid (HOX) and trihalide ion (X3-) must be given serious consideration. Noteworthy is the generation of hypohalous acid and halogen from sulfoxides and hydrohalic acids, apparently involved, for example, in the reductive halogenation of 10-alkylphenothiazines" [Eq.

Raileanu, Ann. 631, 194 (1960). 67 F. Feist and E. Baum, Ber. 38, 3562 (1905). 66 A. Binz and H. Maier-Bode, Biochem. 257, 351 (1933). 69 H. C. van der Plas, H. J. den Hertog, M. van Ammers, and B. Haase, Tetrahedron Letters p. 32 (1961). 70M. Van Ammers, H. J. den Hertog, and B. Haase, Tetrahedron 18, 227 (1962). 7 1 M. Hamana and M. Yamazaki, Chern. Phamz. Bull. ( T o k y o ) 9, 414 (1961); see Chem. Abstr. 55, 24749 (1961). 59*H. 60 SEC. c . 2 1 HALOGENATION O F HETEROCYCLIC COMPOUNDS 21 T A B L E V-continued Heterocycle Halogenating agent Position of attack" Reference ~.

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