By Alan R. Katritzky (ed.)
Meant for natural chemists, this quantity follows the layout of prior volumes and gives updated info on chosen parts of heterocyclic chemistry.
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 38
95 (4Oa) R = C F , (40b) R = CHFCF, H (41) The number of different tetrazines which have been used in this type of reaction (Scheme 5 ) is small and is essentially limited to the species already mentioned. However, a large number of olefins have been treated with these few tetrazines, yielding a large variety of dihydropyridazines. Cycloadditions are also known with diazoalkanes and related compounds. 96*97 Similarly, the Me Me A MeOOC COOMe +CH,N, - MeOOC%Me Me Me MeOOC N’ H 96 97 M. Franck-Neumann and C.
Pharm. Bull. 22,2894 (1974). G . Adembri, F. De Sio, R. Nesi, and M. Scotton, J . Heterocycl. Chem. 12,95 (1975). L. N. Klatt and R. L. Rouseff, J . Electroanal. Chem. Interfacial Electrochem. 41,411 (1973). 38 [Sec. B ALEXANDER L. '" This is probably produced through the intermediacy of 43dihydropyridazine 28a since, according to Lund, neither the 1,2- nor the 1,4dihydro tautomers are expected to be reduced further under the reaction conditions used [Eq. (20)]. flph OHPh - flPh = Ze-+ZH+. Ph N' Ph N/ H Ph N/ H Ph H (2W (75) On the other hand, 3-phenyl-6-dimethylaminopyridazine 76a is reduced smoothly to a 4,5-dihydropyridazine (77a).
Moreover, when deuterated acetone is added to the chloroform solution, equilibrium is displaced toward the 1,Zdihydro derivative (27b). A similar type of tautomerism was found in a series of dihydropyridazines (see Section IV,C) and dihydropyrimidines (see Section V,C,2). For example, on the basis of NMR measurements in CDCI,, it has been shown that 3,6diphenyl-4,5-dihydropyridazine(28a)exists in tautomeric equilibrium with the corresponding 1,4-dihydro compound (28b)in the ratio 1:8. (284 (Db) Furthermore, 'H-and l3C-NMR investigations of 1,2-dihydropyrimidine 21a in CDCI, have demonstrated the existence of tautomeric equilibrium with the corresponding 2,5-dihydro isomer (21b) in the ratio 2: 1 (See Section V,C,2).
Advances in Heterocyclic Chemistry, Vol. 38 by Alan R. Katritzky (ed.)