Publication: Selenium-containing heterocycles from isoselenocyanates: synthesis of 1,2,3-selenadiazole derivatives
Selenium-containing heterocycles from isoselenocyanates: synthesis of 1,2,3-selenadiazole derivatives
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Zhou, Y., & Heimgartner, H. (2000). Selenium-containing heterocycles from isoselenocyanates: synthesis of 1,2,3-selenadiazole derivatives. Helvetica Chimica Acta, 83, 539–553. https://doi.org/10.1002/(SICI)1522-2675(20000315)83:3<539::AID-HLCA539>3.0.CO;2-6
Abstract
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Abstract
The reaction of aroyl chlorides 1 with KSeCN and ethyl diazoacetate (6) in acetone at room temperature yields ethyl 2-aroyl-5-(aroylimino)-2,5-dihydro-1,2,3-selenadiazole-4-carboxylates 7 (Scheme 3). A reaction mechanism via the initial formation of the corresponding aroyl isoselenocyanates 2 followed by a 1,3-dipolar cycloaddition of the diazo compound with the C=Se bond to give ethyl 5-(aroylimino)-4,5-dihydro-1,2,3-selenadiazole-4-carboxylates of type D is proposed. Acylation of the latter at N(2) leads to the final products 7. Dea
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- Zhou, Yuehui
- Heimgartner, Heinz
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Citations
Zhou, Y., & Heimgartner, H. (2000). Selenium-containing heterocycles from isoselenocyanates: synthesis of 1,2,3-selenadiazole derivatives. Helvetica Chimica Acta, 83, 539–553. https://doi.org/10.1002/(SICI)1522-2675(20000315)83:3<539::AID-HLCA539>3.0.CO;2-6
