Publication Details:
Title: An efficient strategy for the construction of X-azatricyclo [m.n.0.0 a,b]alkanes by intramolecular [3 +2] cycloaddition of nonstabilized cyclic azomethine ylides
| Author(s) | Ganesh Pandey,* Akhila K. Sahoo, Trusar D. Bagul, and Smita R. Gadre, : ARKIVOC 2001 (viii) 83-94 |
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More Details:
Various new structural entities related to X-azatricyclo[m.n.0.0.a,b]alkanes 15a-d are constructed
employing the intramolecular [3+2]-dipolar cycloaddition of nonstabilized cyclic azomethine
ylides. The ylides are generated by the sequential double desilylation of N-alkyl-α,α’-
bis(trimethylsilyl)cyclic amines 14a-d using Ag(I)F as a one-electron oxidant. More rigid
azatetracyclo compounds of type 23, in which benzene ring is attached as a tether unit in the Nalkyl
chain moiety, are also synthesized by the cyclization of 22. These rigid azatricyclo
compounds 15 and 23 possess structural resemblance to the rigid azatricyclo analogues 8-10,
which are reported to exhibit selective and high binding affinity at dopamine transporter (DAT).