An Unusual Polyheterocyclic Diversity by the π-Cyclisation of N-Carbamoyl­iminium Ion, with or without Tandem N,N-Acetal Cleavage, from Spiro(imidazolidinoquinazolinones)

Anthony Pesquet; Adam Daïch; Servane Coste; Luc Van Hijfte

doi:10.1055/s-2008-1067032

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Synthesis 2008(9): 1389-1396
DOI: 10.1055/s-2008-1067032

PAPER

An Unusual Polyheterocyclic Diversity by the π-Cyclisation of N-Carbamoyliminium Ion, with or without Tandem N,N-Acetal Cleavage, from Spiro(imidazolidinoquinazolinones)

Anthony Pesquet^a, Adam Daïch*^a, Servane Coste^b,1, Luc Van Hijfte^c
^a URCOM, EA 3221, UFR-ST de l"Université du Havre, 25 rue Philippe Lebon, B.P. 540, 76058 Le Havre Cedex, France
Fax: +33(2)32744391; e-Mail: adam.daich@univ-lehavre.fr;
^b UC2M2 - IRCOF, SMS/UPRES, EA 3233, Université de Rouen, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France
^c Johnson & Johnson, Division of Janssen-Cilag, Campus de Maigremont, B.P. 615, 27106 Val-de-Reuil Cedex, France

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Publication History

Received 9 January 2008
Publication Date:
16 April 2008 (online)

Abstract
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Abstract

Spiro(imidazolidinoquinazolinones), obtained easily in one step from 1-carbamoylisatins, are readily converted in three steps by successive N-alkylations and sodium borohydride regioselective reduction into the corresponding hydroxyspirolactams. The latter are valuable platforms for further transformations via the intermediacy of N-acyliminium species and have been applied to the synthesis of original isoquinoloquinazoline, indoloquinazoline and imidazoindole derivatives.

Key words

π-cyclisation - cleavage - N-acyliminium ion - hydroxy lactam - reduction - imidazolidine - quinazolinone

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1

Present address: CEA Saclay, INSTN-UESMS, 91191 Gif sur Yvette Cedex, France

19

Full crystallographic data have been deposited at the Cambridge Crystallographic Data Centre; CCDC reference number 637457 for product 10b. Copies of the data can be obtained free of charge at the following address:
http://www.ccdc.cam.ac.uk.