Advances in Heterocyclic Chemistry, Vol. 38 by Alan R. Katritzky (ed.)

By Alan R. Katritzky (ed.)

Meant for natural chemists, this quantity follows the layout of earlier volumes and gives updated info on chosen parts of heterocyclic chemistry.

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N. Brown, J. W. Timberlake, and L. M. Trefonas, J. Org. Chem. 38, 1102 7s 76 (1973). J. Dodge, W. Hedges, J. W. Timber1ake;and L. M. Trefonas, J . Org. Chem. 43,3615 (1978). 26 [Sec. B ALEXANDER L. WElS (32) Schlenck and c o - ~ o r k e r showed s ~ ~ that tetrapheylsuccinaldehyde reacted with hydrazine to give 33. These authors did not report any trimerization of the dihydropyridazine. Apparently, the steric requirements of the phenyl groups preclude this eventuality. Ph N’ (33) The single example of the preparation of 1,2-dihydropyridazines (34) was reported by Zelenin and Dumpis,86 namely, the condensation of 1,2dialkylhydrazines with acetonylacetone [Eq.

Scand. 19, 1652 (1965). 'I7 I. Crossland, Acta Chem. Scand. 18, 1653 (1964). 1. Crossland and E. Kelstrup, Acta Chem. Scand. 22, 1669 (1968). A. K. Fateen and N. A. K. Shams, J . Chem. R. 11,301 (1968). I2O E. Kelstrup, Acta Chem. Scand. 23, 1797 (1969). F. G. Baddar, M. H. Nosseir, N. L. Doss, and N. N. S. Perkin I, 1091 (1972). lo' Io9 Sec. B] 35 DIHYDROAZINES mixture of 4-tert-butyl- (62) and 4,5-di-tert-butyl-l,4-dihydroderivatives (63), together with a small amount of the trans-4,5-di-tert-butyl-4,5-dihydropyridazine (64) and other products [Eq.

Welter, and A. Hartmann, Chem. Ber. 112, 2509 (1979). Sec. 86,'03 (52) Aromatic diazonium salts undergo cycloaddition to dienes to produce Nsubstituted 1,6-dihydropyridazines 53 [Eq. @)I. 01 hex2-ene opens thermally to give unsubstituted 4,5-dihydropyridazine (8f) lo3 lo4 S. Stickler and W. C. Hoffmann, Angew. Chem. 82,254 (1970). E. A. Wildi, D. van Engen, and B. K. Carpenter, J . Am. Chem. 102,7994 (1980). 32 [Sec. B ALEXANDER L. WEIS - R$+ArNiX- (8) N' Ar [Eq. (9)]. Under the conditions of their experiment, they found that a dimeric species (which could be characterized only partially because of its instability) was formed along with trimer 32.

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