Amide anions as unexpected activating groups in nucleophilic heteroaromatic substitution

I Gillies, CW Rees

Index: Gillies; Gillies, Iain; Rees; Rees, Charles W. Tetrahedron Letters, 1996 , vol. 37, # 23 p. 4065 - 4068

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Citation Number: 6

Abstract

Abstract: Nudeophilic displacement of halide by alkoxide in pyridazines, phthalazines, a thiazole and a thiadiazole is unexpectedly activated by acetamido anion substituents compared to neutral amido and amino substituents. Copyright © 1996 Elsevier Science Ltd During the synthesis of some pyridazinyl ethers, we made an intriguing observation on the relative reactivities of 3-chloropyridazines towards 3,4,5-trimethoxybenzyi alcohol 2. 3-Amino-6-chloropyridazine l reacted slowly ...