A formal [1 + 2 + 3] annulation of methyleneindolinones with o-alkenyl arylisocyanides has been developed for the general and efficient synthesis of both symmetrical and unsymmetrical indolo[3,2-b]carbazoles. The chemoselectivity of this domino reaction was tuned by a tethered alkenyl group, which enables successive formation of three new bonds and two rings from readily accessible starting materials
已开发了一种亚甲基吲哚酮与邻链烯基芳基异氰酸酯的正式[1 + 2 + 3]环合结构,用于对称和不对称的吲哚[3,2- b ]咔唑的常规合成。该多米诺反应的化学选择性通过束缚链烯基进行调节,该链烯基能够在一次操作中由易于接近的起始原料连续形成三个新键和两个环。此外,该方法被用作生物碱麦拉西唑C合成中的关键步骤。
Selective Synthesis of Polyfunctionalized Pyrido[2,3-<i>b</i>]indoles by Multicomponent Domino Reactions
作者:Jun-Die Hu、Cheng-Pao Cao、Wei Lin、Ming-Hua Hu、Zhi-Bin Huang、Da-Qing Shi
DOI:10.1021/jo501049m
日期:2014.9.5
A series of novel polyfunctionalized pyrido[2,3-b]indoles were synthesized by three- or four-component domino reactions under microwave irradiation. This protocol has the advantages of readily available starting materials, short reaction times, high yields, easy workup, and high chemo- and regioselectivities.
Addition-elimination of nitroalkanes to 3-phenacylideneoxindoles—direct method for the synthesis of 3-alkenylphenacylidene-oxindoles
作者:Yu-Xuan Fu、Shan-Shan Hu、Shao-Yi Li、Xiao-Juan Li
DOI:10.1080/00397911.2019.1587779
日期:2019.4.18
3-Phenacylideneoxindoles with tosylmethyl isocyanide and MeOH through C–C bond cleavage: facile synthesis of pyrrole and 2H-pyrrolo[3,4-c]quinoline derivatives
作者:Rong Wang、Xiao-Ping Xu、Hua Meng、Shun-Yi Wang、Shun-Jun Ji
DOI:10.1016/j.tet.2012.11.088
日期:2013.2
A novel reaction of 3-phenacylideneoxindoles (1) with tosylmethyl isocyanide (2a) and MeOH through C-C bond cleavage has been developed. The reaction proceeded under mild conditions, providing a powerful synthetic tool for the construction of pyrrole derivatives (3) from easily accessible starting materials and synthesis of 2H-pyrrolo[3,4-c]quinolines (4) by further dehydration of 3. (C) 2012 Elsevier Ltd. All rights reserved.