A detailed investigation into the oxidation mechanism of Hantzsch 1, 4-dihydropyridines by ethyl α-cyanocinnamates and benzylidenemalononitriles

…, HL Zou, PW Yuan, Y Liu, L Cao, JP Cheng

Index: Zhu, Xiao-Qing; Zou, Hong-Ling; Yuan, Ping-Wei; Cao, Lei; Cheng, Jin-Pei Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 9 p. 1857 - 1861

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Citation Number: 37

Abstract

The mechanism for the oxidation of Hantzsch 1, 4-dihydropyridine (HEH) by substituted ethyl α-cyanocinnamates (1) and benzylidenemalononitriles (2) has been critically investigated. Replacement of HEH by HEH-4, 4-d2 and HEH-Nd gave the observed kinetic isotope effects (KIE) of 5.3–6.0 and 1.2–1.3 for the reactions with 1 and 2, respectively, which suggests C4– H bond dissociation is involved in the rate-limiting step and that the N–H bond ...

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