Huisgen

Cycloadditions of benzonitril-4-nitrobenzylide to a variety of carbon to heteroatom multiple bonds including methyl dithiobenzoate and dimethyl trithiocarbonate (Scheme 148), X = MeS or Ph, have been examined in detail by Huisgen et al. (757). 

This ring closure is the final step of the reaction of hydrazines with 1,3-difunctional compounds (Section 4.04.3.1.2(ii)), and numerous examples in the literature of pyrazoles have been described. In some cases the N—C ring closure occurs by a concerted mechanism, classified by Huisgen (80AG(E)947) as 1,5-electrocyclizations. 

R. Huisgen, Angew. Chem. Int. Ed. Engl. 2 565 (1963) R. Huisgen, R. Grashey, and J. Sauer, in The Chemistry of the Alkenes, S. Patai, ed.. Interscience Publishers, London, 1965, pp. 806-878 A. Padwa, 1,3-Dipolar Addition Chemistry, John Wiley Sons, New York, 1984. 

In general, reaction of diazomethane with a, -unsaturated carbonyl compounds affords pyrazolines in which the nucleophilic methylene group is attached to the carbon atom of the carbonyl compound. According to Huisgen, the reactions belong to the general class of 1,3-dipolar cycloadditions. 

Dipolar cycloaddUions. Interest in 1,3-dipolar cycloadditions increased dramatically during the past 20 years, largely because of the pioneering studies of Huisgen [7, 2] The versatility of this class of pericychc reactions in the synthesis of five-membered-ring heterocyclic compounds is comparable with that of the Diels-Alder reaction in the synthesis of six-membered-ring carbocyclic systems (equation 1)... 

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