Tetrahedron Letters

[4+ 2] Cycloaddition of 1-phosphono-1, 3-butadiene with azo-and nitroso-heterodienophiles

JC Monbaliu, J Marchand-Brynaert

Index: Monbaliu, Jean-Christophe; Marchand-Brynaert, Jacqueline Tetrahedron Letters, 2008 , vol. 49, # 11 p. 1839 - 1842

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Citation Number: 21

Abstract

Under microwave activation, diethyl 1-phosphono-1, 3-butadiene (1) reacted with t-butyl azodicarboxylate (2) and o-nitrosotoluene (5) to furnish quantitatively [4+ 2] cycloadducts, 3- phosphono-3, 6-dihydro-1, 2-pyridazine (3) and 6-phosphono-3, 6-dihydro-1, 2-oxazine (6), respectively. Selective oxidation and/or reduction of 6 led to functionalized δ- aminophosphonic derivatives in cyclic (7, 8) and aliphatic series (9, 10). Intermediate 10 ...