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The diazatricyclic ketone 3 was synthesized by a double Mannich condensation starting from 2‐quinolizidone (2). Reductions of 3 by complex hydrides and hydrazine gave a mixture of isomeric amino alcohols rac‐4/5 and the diamine 6, respectively. Compounds rac‐4 and rac‐5 could be separated by selective acylation with 4‐chlorobenzoyl chloride due to the fundamental steric differences in the N → O acyl transfer interactions within the isomeric molecules. The cis‐ and trans‐4‐phenyl‐2‐quinolizidones (rac‐10, rac‐11) also underwent a Mannich condensation affording the same product rac‐12 in both cases.

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1‐Cyanomethylene‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinolinium mesylate (10) readily reacted with α,β‐unsaturated aldehydes to afford 1‐azatrienes 12a–h, which could be cyclized to give 6,7‐dihydro‐4H‐benzo[a]quinolizines 14a–h. The reaction mechanisms were investigated by computational methods. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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