1020202-75-8Relevant academic research and scientific papers
Allenyl azide cycloaddition chemistry. 2,3-Cyclopentennelated indole synthesis through indolidene intermediates
Feldman, Ken S.,Hester II, D. Keith,Iyer, Malliga R.,Munson, Paul J.,Lopez, Carlos Silva,Faza, Olalla Nieto
experimental part, p. 4958 - 4974 (2009/11/30)
(Chemical Equation Presented) The thermal, photochemical, and photochemical/CuI-mediated cascade cyclizations of a range of substituted 1-(2-azidophenyl)-3-alkenylallenes are described. These reactions provide both 1,2- and 2,3-cyclopentennelated indole products in varying ratios. In most cases, high regioselectivity for the 2,3-annelated isomer can be achieved under the h?/CuI conditions. Computational studies of this multistep reaction support the intermediacy of indolidene intermediates whose electrocyclizations (with or without copper present) define the regioselectivity branch point in the sequence.
Allenl azide cycloaddtion chemistry. Photochemical initiation and cul mediation leads to improved regioselectivity
Feldman II, Ken S.,Hester, D. Keith,Lpez, Carlos Silva,Faza, Olalla Nieto
supporting information; experimental part, p. 1665 - 1668 (2009/04/10)
Irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess Cul furnished functionalized 2,3-cyclopentenylindoles in good yield with only trace amounts of competitive C-N-bonded regioisomeric products. These results represent a significant departure from the modest to-nonexistent regioselectivity that attended thermal cyclization of these allenyl azide substrates.
