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Synthesis 2002(13): 1871-1878
DOI: 10.1055/s-2002-33909
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Synthetic Route to Hexahydro[1,4]oxazino[2,3-h] and [3,2-j]β-Carboline Derivatives

Stanislas Mayer, Benoît Joseph, Gérald Guillaumet, Jean-Yves Mérour*
Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d’Orléans, BP 6759, 45067 Orléans Cedex 2, France
Fax: +33(2)38417281; e-Mail: jean-yves.merour@univ-orleans.fr ;
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Publication History

Received 6 May 2002
Publication Date:
09 September 2002 (online)

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Abstract

Convenient methods for the regioselective formylation of tetrahydro[1,4]oxazino[2,3-f] and [3,2-g]indole derivatives 3 and 4 are described. The obtained formyl derivatives 6 and 8 were further transformed in four steps into the unknown hexahydro[1,4]oxazino[2,3-h] 1 and [3,2-j]β-carbolines 2.

Key words

oxazinoindoles - regioselective formylation - Vilsmeier-Haack reaction - Rieche reaction

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13

Compound 6a (n = 1, R = H) could be also transformed into the corresponding nitroethyl derivative of type 10 in a total yield of 69%. Hydrogenation over Raney nickel afforded the ethylamine derivative as a relatively stable solid (mp 103-105 °C; 84% yield), which upon heating in toluene afforded the corresponding lactam of the type 11 in only 34% yield. (DBU gave only degradation products).