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Synlett 1999; 1999(9): 1383-1386
DOI: 10.1055/s-1999-2838
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Synthesis of [1,2-b] and [2,1-b]Quinazoline Ring Systems via Suitably Substituted α-Cyanoamines

Erwan Le Gall* , Richard Malassene, Loic Toupet, Jean-Pierre Hurvois, Claude Moinet
  • *Laboratoire d'Electrochimie, Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France; Tel: + 33(2)99 28 62 90; Fax: + 33 0(2)99 28 16 60; E-mail: Jean-Pierre.Hurvois@univ-rennes1.fr
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Publication Date:
31 December 1999 (online)

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A novel entry into tetrahydro-6H-isoquino[1,2-b]quinazoline and hexahydro-5aH-pyrido[2,1-b]quinazoline ring systems is outlined employing 1,2,3,4-tetrahydroisoquinoline and piperidine as starting material. The anodic cyanation of N-substituted aliphatic amines constitute the key step of the synthesis of the quinazolines 3 and 9.

electrochemistry - nitrogen heterocycles - oxidation - tandem reaction - iminium ion