Vishwakarma Ramesh Kumar, Sen Raju, Deshwal Shalu, Vaitla Janakiram
Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India.
J Org Chem. 2024 Dec 20;89(24):18535-18549. doi: 10.1021/acs.joc.4c02484. Epub 2024 Dec 2.
A convenient and practical method has been developed for synthesizing various -aryl pyrazoles from vinyl sulfoxonium ylides and diazonium salts. When using 1,3-disubstituted vinyl sulfoxonium ylides, the reaction selectively yields 1,3,5-trisubstituted pyrazoles. On the other hand, employing 2,3-disubstituted vinyl sulfoxonium ylides results in the formation of 1,3,4-trisubstituted pyrazoles. The reaction proceeds through the novel aryl diazene-derived vinyl sulfoxonium ylide. Furthermore, this method efficiently produces pyrazoles from aniline derivatives in a one-pot transformation. The reaction takes place under transition metal-free, mild conditions using easily accessible starting materials, making it a practical approach for generating pyrazoles in pharmaceutical chemistry.
已经开发出一种方便实用的方法，用于从乙烯基亚砜叶立德和重氮盐合成各种芳基吡唑。当使用1,3-二取代的乙烯基亚砜叶立德时，反应选择性地生成1,3,5-三取代的吡唑。另一方面，使用2,3-二取代的乙烯基亚砜叶立德会导致形成1,3,4-三取代的吡唑。该反应通过新型芳基二氮烯衍生的乙烯基亚砜叶立德进行。此外，该方法在一锅法转化中能有效地从苯胺衍生物制备吡唑。该反应在无过渡金属、温和的条件下进行，使用易于获得的起始原料，使其成为药物化学中生成吡唑的实用方法。
