Annulative Synthesis of Thiazoles and Oxazoles from Alkenyl Sulfoxides and Nitriles via Additive Pummerer Reaction
Annulative Synthesis of Thiazoles and Oxazoles from Alkenyl Sulfoxides and Nitriles via Additive Pummerer Reaction
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DOI：
10.1002/ajoc.201900169
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发表时间：
2019-07
影响因子：
2.7
通讯作者：
Mitsuki Hori;K. Nogi;A. Nagaki;H. Yorimitsu
中科院分区：
文献类型：
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作者：
Mitsuki Hori;K. Nogi;A. Nagaki;H. Yorimitsu
烯基亚砜，主要是烯酮二硫缩醛单氧化物（KDMs）与腈的环化已被开发。以三氟甲烷磺酸酐（Tf2O）为活化剂，由硝基中间体进行添加剂Pummerer反应和随后的C−S键形成环化反应，得到相应的噻唑。此外，硝基中间体被水分子间打断，生成恶唑而不是噻唑。
Pummerer‐based annulation of alkenyl sulfoxides, mainly ketene dithioacetal monoxides (KDMs), with nitriles has been developed. By means of trifluoromethanesulfonic anhydride (Tf2O) as an activator, additive Pummerer reaction and subsequent C−S‐bond‐forming cyclization from the nitrilium intermediates furnished the corresponding thiazoles. Moreover, the nitrilium intermediates proved to be interrupted intermolecularly by H2O to afford oxazoles instead of thiazoles.