Department of Chemistry, University of Delhi, Delhi110007, India.
Department of Chemistry, Netaji Subhas University of Technology, Dwarka Sec-3, Delhi110078, India.
J Org Chem. 2023 Feb 17;88(4):2474-2486. doi: 10.1021/acs.joc.2c02915. Epub 2023 Jan 30.
A regioselective tandem approach for annulated napthyridines/isoquinolines embedded with the phosphine oxide group under mild reaction conditions has been achieved in good to excellent yields. The designed strategy involves the triflate-induced formation of new C sp-P and C sp-N bond formation in one pot. This protocol was also well tolerated for the construction of densely functionalized organo-phosphorylated chromenes in good yields. Further, phosphino-derived sulfamethazine and sulfamethoxazole drugs were also successfully synthesized in good yields. The mechanistic studies revealed that the ionic pathway and the formation of regioselective cyclized products were confirmed through X-ray crystallographic studies. Interestingly, photophysical studies of selectivity selected compounds revealed their stimulating fluorescence properties.
在温和的反应条件下，通过区域选择性串联方法实现了含有膦氧化物基团的并环萘啶/异喹啉，产率良好至优秀。该设计策略涉及三氟甲磺酸酯诱导一锅法中新的 C sp-P 和 C sp-N 键形成。该方案还可以很好地耐受在良好收率下构建稠合官能化的有机磷酰化色烯。此外，还成功地以良好的产率合成了衍生自膦的磺胺甲恶唑和磺胺甲嘧啶药物。通过 X 射线晶体学研究证实了机理研究表明，离子途径和区域选择性环化产物的形成。有趣的是，对选择性化合物的光物理研究揭示了它们具有刺激荧光性质。
