Tetrahedron

A facile synthesis of 5-alkoxypyrrol-2 (5H)-ones using a modified aza-Achmatowicz oxidation

S Kiren, X Hong, CA Leverett, A Padwa

Index: Kiren, Sezgin; Hong, Xuechuan; Leverett, Carolyn A.; Padwa, Albert Tetrahedron, 2009 ,  vol. 65,  # 33  p. 6720 - 6729

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Citation Number: 15

Abstract

An efficient approach to 2, 4-disubstituted pyrroles has been uncovered and is based on an oxidative rearrangement of a furanyl carbamate followed by sequential reaction of the resulting 5-methoxypyrrol-2 (5H)-one with various alkyl lithiates. The final step of the procedure involves heating the ring opened 1-methoxy-5-oxopentylcarbamate with a primary amine. The overall process can be carried out under mild conditions and ...