1446319-72-7Relevant academic research and scientific papers
Potassium tert-Butoxide-Mediated Condensation Cascade Reaction: Transition Metal-Free Synthesis of Multisubstituted Aryl Indoles and Benzofurans
Yang, Pengfei,Xu, Weiyan,Wang, Rongchao,Zhang, Min,Xie, Chunsong,Zeng, Xiaofei,Wang, Min
, p. 3658 - 3662 (2019/05/17)
An efficient and facile method to synthesize valuable disubstituted 2-aryl indoles and benzofurans in good yields has been demonstrated, based on a tert-butoxide-mediated condensation reaction involving a vinyl sulfoxide intermediate. Products are obtained from N- or O-benzyl benzaldehydes using dimethyl sulfoxide as a carbon source. The methodology features a wide functional group tolerance and transition metal-free environment. Preliminary mechanistic studies suggest that the reaction involves a tandem aldol reaction/Michael addition/dehydrosulfenylation/isomerization sequence through an ionic protocol.
Reactivity of tetrahydrochromeno[2,3-b]indoles: Chromic indicators of cyanide
Douglas, Nicholas,Neef, Charles J.,Rogers, Robert A.,Stanley, Jake A.,Armitage, Jacob,Martin, Ben,Hudnall, Todd W.,Brittain, William J.
, p. 688 - 695 (2013/08/23)
The synthesis and reactivity of a tetrahydrochromeno[2,3-b]indoles are reported. Evidence for reversible ring-opening is based on H/D exchange and trapping experiments. These compounds readily undergo reaction with tetra-n-butylammonium cyanide. The cyanide reaction is 10-100× faster when the solution is irradiated with 350 nm light. Reaction with trimethylsilyl cyanide occurs only with UV irradiation demonstrating photoreactivity. The rate of tetrahydrochromeno[2,3-b]indole ring-opening is greater for (i) Me substitution at the hemiaminal carbon (compared to Ph), and (ii) substitution of fluorine at the 9-position of the indole. Under acidic conditions, the ring-opened indolium ion is observed. Copyright
