By A. R. & Boulton, A. J. [Eds]. Katritzky
(from preface)Volume thirteen of this serial book includes six chapters of which 4 take care of common debts of compound sessions: 1-azirines (F. W. Fowler), phenanthridincs (B. R. T. Keene and P. Tissington), tri-thiapentalenes (N. Lozac'h), and heterocyclic fcrrocenes (F. D. Popp and E. B. Moynahan). the opposite chapters are fascinated with specific points of the chemistry of teams of heterocycles: the tautomerism of purines (B. Pullman and A. Pullman) and quantitative features of the electrophilic substitution reactions of five-membercd jewelry (G. Marino).
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 13
98 Ferrocenecarboxaldehyde also reacts with barbituric acid t o give 99,07 with 1,2dimethylpyridinium iodide t o give with a series of substituted M. Furdik, S. Torna, and J. Suchy, Chem. Zwesti 17, 21 (1963);Chem. Abstr. 59, 10116 (1963). 93 J. W. Cusic and P. S. Patent 3,395,144 (1968); Chem. Abstr. 69, 92 964605. (1968). F. D. Popp and E. B. Moynahan, J . Med. Chem. 13, 1020 (1970). 95 J. Tirouflet arid J. Boichard, C. R. Acad. Sci. 250, 1861 (1960). 96 J. Boichard, J. Monin, and J. Tirouflet, Bull.
Cliern. 33, 2121 (1968). K . R . Henery-Logan and T. L. Fridinger, J . Amer. C h e m . 6 0 ~89, . 5724 (1967). 20 G . Smolinsky, J . Org. Chenz. 27, 3557 (1962). 2 1 G. Smolinsky, J . Amer. Chem. SOC. 83, 4483 (1961). 18 19 52 [Sec. B. FRANK W . FOWLER yields of the 1-azirines (42), small amounts (5-6%) of the ketenimines (43)are also formed. The ketenimine results from a migration of the group alpha to the azido function by a Curtius-type rearrangement. N3 RC=CHz I 7 (41) (a) R (b) R (c) R R & H 60-6070 +RN=C===CHz 6-670 (43) (42) = Ph = n-Bu = p-CHa Irradiation of vinyl azides also produces 1-azirines.
Dzurilla, Chem. Zvesti 16, 719 (1962); Chem. Abstr. 59, 3955 (1963). Sec. 1 27 HETEROCYCLIC FERROCENES containing ferrocenyl heterocyclic compounds have been reported. 16a B. 61 These were probably 124 and the 3-ferrocenyl isomer. The reaction of N-ferrocenoylglycine with benzaldehyde and sodium acetate in acetic anhydride gave the oxazolone (125)66 (123) (124) (125) A number of ferrocene-containing 1,3,4-oxadiazoles have been prepared. The reaction of ferrocenecarboxhydrazide with triethyl orthoformate gave three products, the principal one being 2-ferrocenyl-1,3,4-oxadiazole (126; R = H).
Advances in Heterocyclic Chemistry, Vol. 13 by A. R. & Boulton, A. J. [Eds]. Katritzky