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Synthesis 1993; 1993(5): 521-524
DOI: 10.1055/s-1993-25897
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Ring Chain Transformations; X:1 Synthesis of Condensed (ω -Aminoalkyl)imidazoles by Ring Chain Transformation

Jörg Bohrisch* , Michael Pätzel, Jürgen Liebscher, Gerhard Maas
  • *Fachbereich Chemie, Humboldt-Universität Berlin, Hessische Str. 1-2, D-1040 Berlin Germany
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Publication Date:
17 September 2002 (online)

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2-Aminoazaheterocycles 1 react with lactam acetals (2,2-diethoxy-1-methylpyrrolidine, -1-methylpiperidine and -hexahydro-1-methyl-1H-azepine, 2) affording 2-lactamimino azaheterocycles 3. Reaction of the latter with CH-acidic methyl halides 4 allows a ring chain transformation via N-alkylation products 5 resulting in novel 2-[(ω-(methylammonio)alkyl]imidazo[2,1-b]thiazole, -[1,2-a]pyridine and -[1,2-a]pyrimidine halides 7 and the corresponding 2-[ω-(methylamino)alkyl] compounds 8.