Nonneurotoxic tetralin and indan analogs of 3, 4-(methylenedioxy) amphetamine (MDA)

…, WK Brewster, MP Johnson, R Oberlender…

Index: Nichols, David E.; Brewster, William K.; Johnson, Michael P.; Oberlender, Robert; Riggs, Robert M. Journal of Medicinal Chemistry, 1990 , vol. 33, # 2 p. 703 - 710

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Citation Number: 77

Abstract

Indan derivative 3a was prepared from indanone 8a. The latter was prepared in 85% yield by an intramolecular cyclization of 3-[3, 4-(methylenedioxy) phenyl] propionyl chloride. Treatment of the indanone with amyl nitrite in methanol with HC1 afforded the hydroxyimino ketone (Scheme I). 21 This was reduced to the 2-aminoindan following a modification of our earlier method. 18 Compound 4a was prepared by a similar sequence. Methylenation of 2 ...