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This paper describes a selenium-promoted electrophilic cyclization of arylpropiolamides allowing the synthesis of 3-organoselenyl spiro[4,5]trienones via a 5-endo-dig ipso-mode. The 3-organoselenyl-quinolinone derivative formation via 6-endo-dig was avoided using an electrophilic organoselenium species in a metal-free protocol. The use of phenylselenyl bromide (1.3 equiv.), as the electrophilic source, in nitromethane (3 mL) at 90 °C enabled the cyclization of N-(2-methoxyphenyl)-N-methyl-3-phenylpropiolamides, giving 3-organoselenyl[4
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