z-logo
Premium
Michael addition of N ‐isobutylidene‐ t ‐butylamine to dimethyl methoxymethylenemalonate and a new synthesis of some fused pyrazole derivatives from the adduct
Author(s) -
Ito Kunio,
Ihara Shogo,
Miyajima Shingo
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300613
Subject(s) - chemistry , michael reaction , adduct , substituent , pyrazole , alkylation , base (topology) , addition reaction , butylamine , medicinal chemistry , organic chemistry , amine gas treating , catalysis , mathematical analysis , mathematics
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 , tetrahydro‐pyrazolo[5,1‐ b ][1,3]oxazines 9c,d and hexahydropyrazolo[5,1‐ b ][1,3]oxazepine 9e , respectively.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here
Accelerating Research

Address

John Eccles House
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom