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Synthesis 1995; 1995(8): 985-988
DOI: 10.1055/s-1995-4033
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An Efficient, One-Pot Synthesis of 1,3-Thiazines and 1,2,3,5-Thiatriazines from N-(Trimethylsilyl)imines via [4+2] Cycloaddition of 1-Thia-3-azadienes

José Barluenga* , Miguel Tomás, Alfredo Ballesteros, Luis A. López
  • *Instituto Universitario de Química Organometálica ”Enrique Moles”, Universidad de Oviedo, Julián Clavería 8, E-33071-Oviedo, Spain
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Publication Date:
31 December 2000 (online)

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The [4+2] cycloaddition reaction of 2-amino-1-thia-3-azabutadienes 2, formed in situ from N-(trimethylsilyl)imines 1 and phenyl isothiocyanate, towards electron-poor dienophiles is described. The process is applied to a number of carbo- and heterodienophiles, allowing the regioselective formation of the cycloadducts 3-7 with complete endo-stereoselectivity.

1-thia-3-azadienes - heterodienophiles - hetero-Diels-Alder - 1,3-thiazines - 1,2,3,5-thiatriazines