65881-18-7Relevant articles and documents
Indoxyl-based umpolung strategy for the synthesis of unsymmetrical 3,3′-biindoles
Guo, Jing,Weng, Jiang,Huang, Gong-Bin,Huang, Lin-Jie,Chan, Albert S.C.,Lu, Gui
, p. 5493 - 5496 (2016/11/19)
3,3′-Bisindoles are known to be important structural motifs found in bioactive natural products, pharmaceuticals, and functional materials. Herein, a novel indoxyl-based approach was established for the synthesis of unsymmetrical 3,3′-biindoles from indoles and indoxyls. This approach generated moderate to excellent yields of the desired products (24 examples, up to 98% yield). The present method features broad substrate scope, operational simplicity, high atom economy, and utilization of non-toxic and inexpensive molecular iodine as catalyst. The applicability of this method has been demonstrated by the facile gram-scale synthesis.
Synthesis and physical properties of various organic dyes derived from a single core skeleton, 1,2-dihydroindol-3-one
Matsumoto, Shoji,Samata, Daisuke,Akazome, Motohiro,Ogura, Katsuyuki
supporting information; body text, p. 111 - 114 (2009/04/14)
Various organic dyes were synthesized from 1,2-dihydroindol-3-one analogue via Robinson ring annulation, which proceeded efficiently using DBU as a base to give the π-expanded compounds. These compounds exhibited longer Stokes shifts (over 100 nm) than the 1,2-dihydroindol-3-ones (50-80 nm). Emission peaks of the obtained materials covered the 440-640 nm range.
A Novel Synthesis of 1-Acylindoxyls
Chien, Chun-Sheng,Hasegawa, Atsushi,Kawasaki, Tomomi,Sakamoto, Masanori
, p. 1493 - 1496 (2007/10/02)
A novel and efficient synthesis of 1-acylindoxyls (3) from 1-acylindoles (1) is described.The procedure involves the demethoxylation with stannic chloride of 1-acyl-3-hydroxy-2-methoxy-indoline (2), which were obtained by the MoO5 oxidation of 1 in methanol.Since the MoO5 oxidation of 2-substituted 1-acylindoles (1f and 1g) gave not the corresponding indolines (2f and 2g), but 2-hydroxyindoxyls (4f and 4g), 2f and 2g were obtained by the methylation of 4f and 4g with diazomethane to give 5f and 5g, followed by the reduction of 5f and 5g with sodium borohydride, respectively.Keywords - indoxyl; indole; indoline; oxidation; demethoxylation; peroxomolybdenum complex; methylation; diazomethane; reduction; sodium borohydride
