1144102-65-7Relevant academic research and scientific papers
Acid-catalyzed highly diastereoselective and effective synthesis of 1,3-disubstituted tetrahydropyrano[3,4-b]indoles
Wang, Pei,Zhao, Jia-Zhen,Li, Hong-Feng,Liang, Xiang-Ming,Zhang, Ya-Lun,Da, Chao-Shan
, p. 129 - 133 (2017)
We successfully explored for the first time that trifluoroacetic acid (TFA) can effectively catalyze the oxa-Pictet-Spengler reaction of secondary tryptophols and acetals to synthesize 1,3-disubstituted 1,3,4,9-tetrahydropyrano[3,4-b]indoles in high yield (up to >99%) and diastereoselectivity (>20:1). The secondary tryptophols were synthesized from indole-3-acetic acid. The one-pot synthesis of tetrahydropyrano[3,4-b]indoles was successfully developed from secondary tryptophols and in situ prepared acetals from aldehydes and trimethylorthoformate and thus the cost-efficiency of the protocol was effectively enhanced. Finally, the catalytic asymmetric synthesis of the 1,3-disubstituted tetrahydropyrano[3,4-b]indole was also demonstrated after enantioselective achievement of highly enantiopure secondary tryptophols.
Transition-Metal-Free Intermolecular α-Arylation of Ketones via Enolonium Species
Maksymenko, Shimon,Parida, Keshaba N.,Pathe, Gulab K.,More, Atul A.,Lipisa, Yuriy B.,Szpilman, Alex M.
, p. 6312 - 6315 (2017)
Herein it is shown, for the first time, that enolonium species are powerful electrophiles capable of reacting with aromatic compounds in an intermolecular manner to afford α-arylated ketones. The reaction is compatible with a variety of functional groups, is of wide scope with respect to aromatic compounds and ketone, and even works for polymerization-prone substrates such as substituted pyrroles, thiophenes, and furans. Only 1.6 to 5 equiv of the commodity aromatic substrates is needed.
Iodine-induced regioselective direct alkylation of azoles via in situ formed alkyliodide
Chen, Wenlin,Yan, Rulong,Tang, Dong,Guo, Shuaibo,Meng, Xu,Chen, Baohua
supporting information; experimental part, p. 7956 - 7959 (2012/09/21)
We have developed an efficient, metal-free, convenient and relatively cheap method for iodine-induced direct alkylation of azoles via in situ formed alkyliodide. A series of heterocyclic derivatives are readily prepared under mild conditions in moderate t
