90312-02-0Relevant articles and documents
Transition metal-free approach to azafluoranthene scaffolds by aldol condensation/[1+2+3] annulation tandem reaction of isocyanoacetates with 8-(alkynyl)-1-naphthaldehydes
Dong, Penghui,Majeed, Kashif,Wang, Lingna,Guo, Zijian,Zhou, Fengtao,Zhang, Qiuyu
, p. 4855 - 4858 (2021/05/25)
A transition metal-free aldol condensation/[1+2+3] annulation reaction of isocyanoacetates with 8-(alkynyl)-1-naphthaldehydes has been developed for the general synthesis of azafluoranthenes. This domino reaction enables successive formation of three new bonds and two rings from readily accessible starting materials in a single operation. Furthermore, this methodology can also be utilized to construct chromeno[4,3-c]pyridines and benzo[c][2,6]naphthyridines in moderate yields.
A [4+3] Cycloaddition Reaction of Aza-ortho-quinone Methides with C,N-Cyclic Azomethine Imines for Synthesis of 1,2,4-Triazepines
Wang, Xinyue,Li, Zefei,Feng, Chang,Zhen, Qi,Guo, Mingzhang,Yao, Yaning,Zou, Xinyu,Wang, Pengfei,Hou, Yunlei,Gong, Ping
, p. 2090 - 2096 (2021/09/06)
The base-induced formal [4+3] cycloaddition reaction of C,N-cyclic azomethine imines with aza-ortho-quinone methides, generated in situ, is reported. This protocol provided an efficient method for the synthesis of biologically important 1,2,4-triazepine derivatives, with a wide substrate scope and excellent functional-group tolerance, and it gives moderate to excellent yields under mild conditions. Several of the derivatives exhibited in vitro antitumor activities against the A2780 cell line in a screening of the cancer cell lines HCT-116, H2228, and A2780 by an MTT assay.
Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines
Chen, Yang-Bo,Sun, Zhou,Wang, Ze-Shu,Ye, Long-Wu,Zhang, Hao-Wen,Zhu, Chunyin
, p. 3636 - 3644 (2020/03/06)
In the past decades, significant advances have been made on radical Smiles rearrangement. However, the eventually formed radical intermediates in these reactions are limited to the amidyl radical, except for the few examples initiated by a N-centered radical. Here, a novel and practical radical Smiles rearrangement triggered by photoredox-catalyzed regioselective ketyl-ynamide coupling is reported, which represents the first radical Smiles rearrangement of ynamides. This method enables facile access to a variety of valuable 2-benzhydrylindoles with broad substrate scope in generally good yields under mild reaction conditions. In addition, this chemistry can also be extended to the divergent synthesis of versatile 3-benzhydrylisoquinolines through a similar ketyl-ynamide coupling and radical Smiles rearrangement, followed by dehydrogenative oxidation. Moreover, such an ynamide Smiles rearrangement initiated by intermolecular photoredox catalysis via addition of external radical sources is also achieved. By control experiments, the reaction was shown to proceed via key ketyl radical and α-imino carbon radical intermediates.