503590-28-1Relevant academic research and scientific papers
Highly substituted 2-amido-furans from rh(ll)-catalyzed cyclopropenations of ynamides
Li, Hongyan,Hsung, Richard P.
supporting information; experimental part, p. 4462 - 4465 (2009/12/24)
Rh(II)-catalyzed cyclopropenations of ynamides are described. Although an actual amido-cyclopropene intermediate may not be involved, these reactions provide a facile entry to highly substituted 2-amido-furans, thereby formerly constituting a [3 + 2] cycloaddition. An application of these de novo 2-amido-furans In N-tethered intramolecular [4 + 2] cycloadditions is also illustrated, leading to dihydroindoles and tetrahydroqulnolines
Copper(II)-catalyzed amidations of alkynyl bromides as a general synthesis of ynamides and Z-enamides. An intramolecular amidation for the synthesis of macrocydic ynamides
Zhang, Xuejun,Zhang, Yanshi,Huang, Jian,Hsung, Richard P.,Kurtz, Kimberly C. M.,Oppenheimer, Jossian,Petersen, Matthew E.,Sagamanova, Irina K.,Shen, Lichun,Tracey, Michael R.
, p. 4170 - 4177 (2007/10/03)
A general and efficient method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C-N bond formation, leading to a structurally diverse array of ynamides including macrocyclic ynamides via an intramolecular amidation. Given the surging interest in ynamide chemistry, this atom economical synthesis of ynamides should invoke further attention from the synthetic organic community.
Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides
Zhang, Yanshi,Hsung, Richard P.,Tracey, Michael R.,Kurtz, Kimberly C. M.,Vera, Eymi L.
, p. 1151 - 1154 (2007/10/03)
(Equation presented) A practical cross-coupling of amides with alkynyl bromides using catalytic CuSO4·5H2O and 1,10-phenanthroline is described here. This catalytic protocol is more environmentally friendly than the use of CuCN or copper halides and provides a general entry for syntheses of ynamides including various new sulfonyl and heteroaromatic amine substituted ynamides. Given the interest in ynamides, this N-alkynylation of amides should be significant for the future of ynamides in organic synthesis.
A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides
Frederick, Michael O.,Mulder, Jason A.,Tracey, Michael R.,Hsung, Richard P.,Huang, Jian,Kurtz, Kimberly C. M.,Shen, Lichun,Douglas, Christopher J.
, p. 2368 - 2369 (2007/10/03)
A copper-catalyzed new C-N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides. This direct N-alkynylation of amides should have a significant impact on the future development of synthetic methodologies employing ynamides. Copyright
