jo8b02152_si_002.cif (17.01 kB)
Substrate-Controlled Domino Reactions of Crotonate-Derived Sulfur Ylides: Synthesis of Benzothiophene Derivatives
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posted on 2018-10-29, 00:00 authored by Wenhuan Ding, Youquan Zhang, Aimin Yu, Lei Zhang, Xiangtai MengSubstrate-controlled domino reactions
between thioaurones or their analogues and crotonate-derived sulfur
ylides were developed and produced a broad spectrum of benzothiophene-fused
pyran derivatives, substituted chromene derivatives. In these reactions,
crotonate-derived sulfur ylides acting as two-carbon synthons (α
and β carbons or β and γ carbons) in annulation
reactions are reported for the first time. These investigations nicely
complement and expand previously studied reactions of crotonate-derived
sulfur ylides. In addition, reaction mechanisms for these domino reactions
are proposed, one of which is supported by DFT calculations.
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Keywords
annulation reactionsγ carbonsreaction mechanismsdomino reactionsβ carbonschromene derivativesDFT calculationsSubstrate-Controlled Domino Reactionscrotonate-derived sulfur ylidesCrotonate-Derived Sulfur YlidesBenzothiophene Derivatives Substrate-controlled domino reactionsbenzothiophene-fused pyran derivatives
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