4.5 Article

A Facile and Practical Solvent-Free One-Pot Synthesis of (Z)-4-Methylene-3-selenaquinoline Derivatives from o-Ethynylanilines and Isoselenocyanates

Journal

SYNTHESIS-STUTTGART
Volume -, Issue 18, Pages 3091-3096

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1258171

Keywords

o-ethynyaniline; isoselenocyanate; 3-selenaquinoline; 6-exo mode cyclization; microwave

Funding

  1. Ministry of Education, Science and Culture, Japan [19590022]
  2. Grants-in-Aid for Scientific Research [19590022] Funding Source: KAKEN

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Heating of o-ethynylanilines with isoselenocyanates directly resulted in the 6-exo-dig mode ring-closure reaction of the adducts to give the (Z)-2-imino-4-methylene-3-selenaquinolines in moderate to good yields. Based on this convenient, solvent-free, catalyst-free method, several 3-selenaquinoline derivatives (3,1-benzoselenazines) were easily obtained in one pot. Successful application of the microwave-assisted synthesis of these compounds was also investigated.

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