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Synthesis 2011(3): 413-418  
DOI: 10.1055/s-0030-1258386
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient and Highly Selective Method for the Synthesis of 4-Iodo-3-substituted 1H-Isoselenochromenes and -isothiochromenes

Caroline C. Schneidera, Cristiani Bortolattoa, Davi F. Backb, Paulo H. Menezesc, Gilson Zeni*a
a Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, CCNE, UFSM, Santa Maria, Rio Grande do Sul CEP 97105-900, Brazil
Fax: +55(55)32208978; e-Mail: gzeni@pq.cnpq.br;
b Laboratório de Materiais Inorgânicos, CCNE, UFSM, Santa Maria, Rio Grande do Sul, 97105-900, Brazil
c Universidade Federal de Pernambuco, Departamento Química Fundamental, Recife, Pernambuco 50670-901, Brazil
Further Information

Publication History

Received 5 October 2010
Publication Date:
23 December 2010 (online)

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Abstract

We present here our results on the preparation of 2-alkynylbenzyl selenide and sulfide derivatives via Sonogashira cross-coupling of benzyl chalcogenides with different alkynes. This cross-coupling reaction proceeded cleanly under mild conditions and was performed with propargyl alcohol as well as alkyl- and arylalkynes. Subsequent electrophilic-cyclization reaction of the 2-alkynylbenzyl selenide and sulfide derivatives using iodine as an electrophilic source gave 4-iodo-3-substituted 1H-isoselenochromenes and -isothiochromenes in moderate yields. The unique product obtained during the course of this cyclization contained a six-membered ring which was confirmed by X-ray diffraction analysis.

Key words

selenides - isochromenes - electrophilic cyclization - heterocycles

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Special issue: Heterocycles, Chem. Rev. 2004, 104, 2125.