Synthetic 1, 4-disubstituted 1, 4-dihydro-5H-tetrazol-5-one derivatives of fentanyl: alfentanil (R 39209), a potent, extremely short-acting narcotic analgesic

F Janssens, J Torremans…

Index: Janssens, Frans; Torremans, Joseph; Janssen, Paul A.J. Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2290 - 2297

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Citation Number: 45

Abstract

The synthesis of a series of Nl, 4-disubstituted-l, 4-dihydro-5H-tetrazol-5-one piperidinyl derivatives of fentanyl (lo), carfentanil (ll), and sufentanil (l2) is described. The 1-substituted tetrazolinones 2 were essentially prepared via the addition reaction of aluminum azide to isocyanates or acid chlorides in tetrahydrofuran. Alkylation of 2 under neutral or weakly basic conditions afforded almost exclusively the 1, 4-disubstituted tetrazolinone isomer 3. ...