Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 13, Pages 2646-2652Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201692
Keywords
Synthetic methods; Electrophilic cyclization; Alkynes; Heterocycles; Selenium; Chalcogens
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Funding
- Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq/INCT-catalise)
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (SAUX)
- Fundacao de Amparo a Pesquisa do Estado do Rio Grande do Sul (FAPERGS) [PRONEX-10/0005-1]
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We present here a practical synthesis of multifunctional imidazo[2,1-b]chalcogenazoles through electrophilic cyclization of N-alkynyl-2-(organochalcogen)imidazoles. The cyclization reaction proceeded cleanly and smoothly under mild reaction conditions in the presence of air. The methodology was highly regioselective: In a competition between the chalcogen and oxygen atoms, only S-, and Se-heterocycles were obtained. The resulting imidazo[2,1-b]chalcogenazoles proved to be versatile as precursors for the synthesis of more highly functionalized imidazoselenazoles through copper-catalyzed cross-coupling reactions with arene- and alkanethiols, leading to Ullmann-type products in good yields.
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