Advances in Heterocyclic Chemistry, Vol. 19 by A. R. & Boulton, A. J. [Eds]. Katritzky

By A. R. & Boulton, A. J. [Eds]. Katritzky

The current quantity contains 4 chapters. the 1st (by Ollis and Ramsden) classifies and discusses the chemistry of that attention-grabbing team of compounds referred to as meso-ionic heterocycles and incorporates a invaluable basic definition of the time period. the second one bankruptcy (Litvinov and Gol'dfarb) bargains with platforms with (or extra) thiophene (or selenophene) jewelry without delay fused jointly. The 1,2,3-triazines, besides the better-known 1,2,3-benzotri-azines and different fused 1,2,3-triazine structures, are mentioned within the 3rd bankruptcy, by way of Kobylecki and McKillop. within the final bankruptcy George, Khetan, and Gupta deal with heterocyclic syntheses which contain the addition of nucleo-philic reagents to acetylenic esters.

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Egorochkm, Khim. Geterotsikl. , 1345 (1973) [CA 80,271752 1974)j; A. Ya. Lazaris and A. N. , 648 (1975) [CA 83, 79164b '00 (1975)l. R. N. Hanley, W. D. Ollis,C. A. Ramsden, G. R. Rowlands, and L. E. Sutton, J. Chem. , Perkin Trans. II, in press (1976). Sec. El 35 MESO-IONIC COMPOUNDS tainedlo9by heating in pyridine the methiodide (157, R' = Me, R2= Ph) derived from 2-phenyl-4-methylthio-1,3,4-oxadiazole (I 58). Subsequently three general methods for the synthesis of meso-ionic 1,3,4oxadiazole-2-thiones (156) have been described.

Chem. ,734 (1951). 82H. Kato, K. Tsnaka, and M. Ohta,Bull. Ckem. Soc. Jap. 35, 1901 (1962). H. Kato, K. Tanaka, and M. Ohta, Bull. Ckem. Soc. Jap. 39, 1248 (1966). Sec. 84-86 However, N-acetyl derivatives (126, R3= Ac) are formed by acetylation of the salts 126, R3 = H, and then treatment with base does yield N-acetyl derivatives of the meso-ionic 1,3-thiazol-4-imines (124, R3= A c ) . 86 R2 / R' s v R R 3 R4 (124) RZ R' ~1 )=N/ p i ' R2 ~1 x- "YCN R4 (125) S qR4 h ' H R 3 R2 " YR4O N H 2 (126) (127) The N-acetyl derivatives of the 2-alkylthio-1,3-thiadiazol-4-imines R' = SR, R3 = Ac) undergo nucleophilic displacement reaction with amines (benzylamine, cyciohexylamine, morpholine, or aniline) giving the 2-amino derivatives (124, R1= NR,, R3= A c ) .

McKeough, J. Amer. Chem. Soc. 95, 2749 (1973); (c) K. T. Potts and J. Baum, J. Chem. ,Chem. , 833 (1973); (d) H. Matsukubo and H. , 412 (1974); J. Chem. ,Perkin Trans. Eicher and V. -D. Hekman, Angew. , Ed. Engl. 11, 926 (1972). 47 G. -P. Fleury, Bull. Soc. Chim. , 4636 (1968). 45 Sec. C,H,) as supporting the meso-ionic structure (77). 007%. They have also shown that azlactones 76 + 77 participate in 1,3-dipolar cycloaddition with a l k y n e ~ ~ ~ * ~ ~ and a l k e n e ~ In . ~ view ~ of the extensive earlier studies of azlactones (76), it is remarkable that their tautomerism with meso-ionic 1,3-oxazol-5ones (77) should have been recognized so recently.

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