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

Caroline C. Schneider; Cristiani Bortolatto; Davi F. Back; Paulo H. Menezes; Gilson Zeni

doi:10.1055/s-0030-1258386

PAPER

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

Caroline C. Schneider^a, Cristiani Bortolatto^a, Davi F. Back^b, Paulo H. Menezes^c, 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

Abstract

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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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References

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