70490-76-5Relevant academic research and scientific papers
Lanthanide-Catalyzed Reversible Alkynyl Exchange by Carbon–Carbon Single-Bond Cleavage Assisted by a Secondary Amino Group
Shao, Yinlin,Zhang, Fangjun,Zhang, Jie,Zhou, Xigeng
, p. 11485 - 11489 (2016/10/24)
Lanthanide-catalyzed alkynyl exchange through C?C single-bond cleavage assisted by a secondary amino group is reported. A lanthanide amido complex is proposed as a key intermediate, which undergoes unprecedented reversible β-alkynyl elimination followed by alkynyl exchange and imine reinsertion. The in situ homo- and cross-dimerization of the liberated alkyne can serve as an additional driving force to shift the metathesis equilibrium to completion. This reaction is formally complementary to conventional alkyne metathesis and allows the selective transformation of internal propargylamines into those bearing different substituents on the alkyne terminus in moderate to excellent yields under operationally simple reaction conditions.
Synthesis of substituted quinolines by the electrophilic cyclization of n-(2-alkynyl)anilines
Zhang, Xiaoxia,Yao, Tuanli,Campo, Marino A.,Larock, Richard C.
experimental part, p. 1177 - 1187 (2010/04/02)
A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I2, Br2, PhSeBr, and p-O2NC6H4SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the 3-position have been synthesized by the Hg(OTf)2-catalyzed ring closure of these same alkynylanilines.
Synthesis of substituted quinolines by electrophilic cyclization of N-(2-alkynyl)anilines
Zhang, Xiaoxia,Campo, Marino A.,Yao, Tuanli,Larock, Richard C.
, p. 763 - 766 (2007/10/03)
(Chemical Equation Presented) Quinolines substituted in the 3-position by an iodo or phenylseleno group are readily prepared in good to excellent yields by the reaction of propargylic anilines with appropriate electrophiles under mild reaction conditions.
