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Anticonvulsants related to U-54494 prepared from cis-1,2- and cis-2,3-diaminotetralin

โœ Scribed by Stan V. D'Andrea; Jeremiah P. Freeman; Philip F. VonVoigtlander; Jacob Szmuszkovicz

Book ID
104204070
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
438 KB
Volume
47
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

cis-Diaminotetralins

4 and 10 were converted in 4 steps to benzologs of the novel anticonvulsant U-54494.

Attempted alkylation of 4 and 70 with 1,4-dibromobutane provided mixtures of the bis-pyrrolidino compounds and starting free bases together with the desired monopyrrolidino compounds 5 and 7 7. Treatment of these mixtures with ethyl chloroformate followed by chromatographic separation gave the carbamates 7 and 12. Reduction of these carbamates with LiAIH4 provided the N-methylamino compounds 8 and 14. Finally, benzamide formation gave rise to the analogs of U-54494, compounds 9 and 15.

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A preliminary communication of one part of this work was published [I]. However, during the writing of this manuscript, such an approach was published [S] \* ' 1) NaEH.. MeOH (92%) 2) NaOH, MeOH/H,O; DMSO 130"C(85%) 3) LiHMDS, 4-PhC8H,COCl (85%) or (f-Eu)Me,SiCi, 1H-imidazole (88%)