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Paper | Regular issue | Vol 38, No. 10, 1994, pp.2171-2181
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6746
A New Type of Highly Polar 1,3-Dipoles. Synthesis and Chemistry of Thiocarbonyl-stabilized Pyrazolidinazomethineimies

Helmut Dorn* and Thomas Kreher

*Abt. Organische Synthese, Institut für Angewandte Chemie Berlin-Adlershof, Rudower Chaussee 5, D-12489, Berlin, Germany


3-Thioxopyrazolidine-azomethineimines (2) are synthesized from their 3-oxo analogues (1) and Lawesson‘s reagent (LR). The electron structures of 1 and 2 resemble those of polymethines, dipole moments of 2 are even higher than those of 1; further physical organic data are discussed. With NaBH4 2 gives 3-thioxopyrazolidines (8). These are S-mono- (10) and (N-1), S-bisalkylated (11). S-Alkylation of 2 affords pyrazolinium salts (7). 1,3-Dipolar cycloaddition of enamines to 2 results in [p4S +p2S] products (12, 13), HOMO/LUMO energies of 1 and 2 are given. Models of γ-thiolactams (17, 19), mimicing antibiotics, are gained via 1,3-dipolar cycloadducts of 1 with LR.