- Indoline Catalyzed Acylhydrazone/Oxime Condensation under Neutral Aqueous Conditions
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Acylhydrazones formation has been widely applied in materials science and biolabeling. However, their sluggish condensation rate under neutral conditions limits its application. Herein, indolines with electron-donating groups are reported as a new catalyst scaffold, which can catalyze acylhydrazone, hydrazone, and oxime formation via an iminium ion intermediate. This new type of catalyst showed up to 15-fold rate enhancement over the traditional anilinecatalyzed reaction at neutral conditions. The identified indoline catalyst was successfully applied in hydrogel formation.
- Zhou, Yuntao,Piergentili, Irene,Hong, Jennifer,Helm, Michelle P. Van Der,MacChione, Mariano,Li, Yao,Eelkema, Rienk,Luo, Sanzhong
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supporting information
p. 6035 - 6040
(2020/10/02)
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- Convenient synthesis of 7-hydroxyindole
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7-Hydroxyindole, the key building block for the synthesis of AJ-9677 1, was prepared from indoline in six steps in 36% overall yield. AJ-9677 1 is a potent and selective adrenaline β3-agonist being considered as a clinical candidate to treat obesity in those who are suffering from diabetes.
- Ishiyama, Kazunao,Yamada, Yasuhiro
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p. 1021 - 1022
(2007/10/03)
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- FURTHER OBSERVATIONS ON THE LEWIS ACID-CATALYZED BENZYLIC HYDROPEROXIDE REARRANGEMENT: USE OF A BORON-TRIFLUORIDE/HYDROGEN PEROXIDE PREFORMED, AGED REAGENT
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A preformed, aged reagent derived from boron trifluoride etherate and 90percent hydrogen peroxide (2:1-4:1 complex) has been found to be a useful reagent for promoting the benzylic hydroperoxide rearrangement of readily oxidizable substrates bearing a free, basic amine.The use of this procedure for introduction of the C-4 phenol of the C-4/C-5 selectively-protected o-catechol unit found in PDE-I and PDE-II, naturally-occuring phosphodiesterase inhibitors constituting the central and right-hand segments of the antitumor-antibiotic CC-1065, is detailed.
- Boger, Dale L.,Coleman, Robert S.
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p. 1027 - 1030
(2007/10/02)
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