Journal of Heterocyclic Chemistry p. 1529 - 1532 (1993)
Update date:2022-07-30
Topics:
Ito
Ihara
Miyajima
N-Isobutylidenemethylamine reacted with dimethyl methoxymethylenemalonate to afford the N-alkylation product 3a exclusively. Exchanging the N- substituent of the Schiff's base from methyl to t-butyl altered the course of the reaction, allowing Michael addition to take place predominantly. The Michael adduct 4c on reaction with hydrazinoalkanols 6a,b, 6c,d and 6e gave tetrahydropyrazolo[5,1-b]oxazoles 9a,b, tetrahydropyrazolo[5,1- b][1,3]oxazines 9c,d and hexahydropyrazolo[5,1-b][1,3]oxazepine 9e, respectively.
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