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Synlett 2010(19): 2956-2958  
DOI: 10.1055/s-0030-1259034
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Preparation of Heteroaromatic Compounds from Alkenes

Timothy J. Donohoe*a, Mikhail A. Kabeshova,b, Akshat H. Rathia, Ian E. D. Smithb
a Department of Chemistry, University of Oxford, Chemistry Reasearch Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
Fax: +44(1865)275674; e-Mail: timothy.donohoe@chem.ox.ac.uk;
b GlaxoSmithKline Research and Development Limited, Medicines Research Centre, Gunnels Wood Road, Stevenage, SG1 2NY, UK
Fax: +44(1438)764502; e-Mail: ian.e.smith@gsk.com;
Further Information

Publication History

Received 11 October 2010
Publication Date:
10 November 2010 (online)

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Abstract

A series of aromatic heterocycles, thiazoles, imidazoles, and dimethoxyindoles, can be synthesised directly from alkenes via a ketoiodination-cyclisation protocol. The alkene starting materials are themselves easily accessible by many different and well-established approaches, and allow access to various aromatic hetero­cycles with excellent yields and regioselectivity.

Key words

heterocycles - alkenes - iodine - iodo ketones - oxidation

    References and Notes

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0.25 M solution, analysed by LCMS calibrated with nitrobenzene; see Supporting Information for details.

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In the reaction of 2-chloro-1-phenylpropan-1-one with benzamidine in the presence of K2CO3 at r.t. in DMF, only traces of the corresponding imidazole were detected after
2 h.

16

To distinguish between two isomeric aminothiazoles: 5-propyl-4-(3-pyridinyl)-1,3-thiazol-2-amine and 4-propyl-5-(3-pyridinyl)-1,3-thiazol-2-amine.