2-碘芳基烯丙基胺的自由基环化与 2-氮杂烯丙基偶联合成色胺类化合物。
Synthesis of Tryptamines from Radical Cyclization of 2-Iodoaryl Allenyl Amines and Coupling with 2-Azallyls.
机构信息
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104, United States.
Department of Chemistry, Tsinghua University, Beijing 100084, China.
出版信息
J Org Chem. 2022 Jun 17;87(12):8099-8103. doi: 10.1021/acs.joc.2c00767. Epub 2022 Jun 8.
An efficient synthesis of tryptamines is developed. Indole structures were constructed using 2-iodoaryl allenyl amines as electron acceptors and radical cyclization precursors. Radical-radical coupling of indolyl methyl radicals and azaallyl radicals led to the tryptamine derivatives. The utility and versatility of this method are showcased by the synthesis of 22 examples of tryptamines in ≤88% yield. In each case, indole formation is accompanied by in situ removal of the Boc protecting group.
开发了一种高效合成色胺的方法。吲哚结构是通过 2-碘芳基烯基胺作为电子受体和自由基环化前体构建的。吲哚基甲基自由基和氮烯自由基的自由基-自由基偶联导致色胺衍生物的生成。该方法的实用性和多功能性通过 22 个色胺的合成得到了展示，产率最高可达 88%。在每种情况下，吲哚的形成伴随着 Boc 保护基的原位去除。
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