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 ok. Mockel), and diquinolylme-thanes (G. Scheibe and E. Daltrozzo). extra chapters care for functions of mass spectrometry to heterocycles (G. Spiteller), a space which has accelerated very speedily of overdue, and the halogenation of heterocycles (J. J. Eisch). eventually, a precis is given of stories within the heterocyclic box, labeled by means of topic (A. R. Katritzky and S. M. Weeds), which it truly is was hoping can be of tips in literature surveys.Suggestions are welcomed for contributions to additional volumes; they need to be within the type of a quick synopsis.Thanks are as a result of the Editorial Board, the publishers, and the authors for his or her cooperation.
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Extra info for Advances in Heterocyclic Chemistry
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 ~. ~ 2-Quinolone ICI in HOAc (Brz in HOAc) Quinoline-N-oxide Brz (HzO at 100') 2-Ethoxyquinoline B i g Coumarin Brz i n CSz : pyridinelheat Phenanthridone Clz, Br, or KI-KI03 in HOAc 3-IOdo (6bromo) 4-Bromo 4-Bromo 3,C-Dibromo adduct 3-Bromo 2-Halo 55, 72 73 74 75 76 a T h e heterocycle numbering is that recommended by A.
Rev. 57,531-532 (1957). 36 [SEC. 111. F. JOHN J. EISCH ring simply reflects the deactivation of the heterocyclic ring and the greater stability of structures of type 30 over those of type 31 (of. alpha substitution in naphthalene). :6) 1, 10, 8, 3, 2, and 4 (38: 31 :16: 9: 1:4) 7,10, and 9 (87: 1 : 13) 1 1 and 3 (83: 17) ~~ ~ M. J. Dewar and P. M. Maitlis, J . Chem. 1957, 2521. E (30) E (31) F. UNSOLVED PROBLEMS AND VISTASOF RESEARCH As with most fields of chemical research, the synthetic aspects of heterocyclic halogenation have been mastered far better than have the underlying reaction mechanisms.
Orazi, and J. F. Salellas, Anales Asoc. Quim. Arg. 39, 184 (1951);see Chem. Abstr. 47, 2709 (1953). 50 51 J. 20 JOHN J. EISCH [SEC. 2 TABLE V-continued Heterocyc1e Halogenating agent Reference 2-Bromo 2,7-Dibromo 2-Bromo Acridine Br2 in HOAc Phenanthridine Dibenzo-p-dioxin Phenazine Br2 in HOAc NBSb in C c 4 Cl2 or KBr-KBrO3 Cl2 in cc14 Thianthrene Phenoxathiin Phenoxazine Brg in HOAc Br2 in ccl4 Br2 in c6H1j Phenothiazine Cl2, Br2, or HCl/H202 4-Pyrone 2-Pyridone Br2 (Fed%) Cl2, Bra, or 1 2 Pyridine-N-oxide Position of attack" in HOAc 2-Halo 1-Chloro 1,4-Dichloro 2-Bromo 2-Bromo 3-Bromo 3,7-Dibromo 3-Halo 3,7-Dihalo 4.
Advances in Heterocyclic Chemistry by Alan R. Katritzky