333383-93-0Relevant academic research and scientific papers
Unusual Skeletal Reorganization of Oxetanes for the Synthesis of 1,2-Dihydroquinolines
Guo, Wengang,Huang, Hai,Qian, Chenxiao,Sun, Jianwei,Wang, Guannan
supporting information, p. 11245 - 11249 (2020/05/29)
Skeletal reorganization is a type of fascinating transformations owing to their intriguing mechanisms and utility in complex molecule synthesis. However, only a limited amount of examples are known for most functional groups. Herein, we describe such an unusual process of oxetanes. In the presence of In(OTf)3 as catalyst, oxetane-tethered anilines reacted unexpectedly to form 1,2-dihydroquinolines. This process not only provides expedient access to dihydroquinolines, but also represents a new reaction of oxetane. Mechanistically, it is believed that the reaction proceeds through initial nitrogen attack rather than arene attack followed by a series of bond cleavage and formation events. Control experiments provided important insights into the mechanism.
One-pot preparation of 7-hydroxyquinoline
Cameron, Mark,Hoerrner, R. Scott,McNamara, James M.,Figus, Margaret,Thomas, Scott
, p. 149 - 152 (2012/12/21)
An efficient one-pot procedure for the four-step preparation of 7-hydroxyquinoline (1) from 3-N-tosylaminophenol (4) in 60% isolated yield, that reduces the risk of exposure to acrolein (2), is described.
Intermediates for synthesis of vinblastine compound and method for synthesizing the intermediate
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Page 4; 5, (2010/11/30)
Intermediates A, which are important in the whole synthesis of vindoline; and a method of synthesizing intermediates respectively represented by the general formulae B and C. By the method, the target intermediates are effectively synthesized with satisfactory reproducibility. This synthesis method is especially suitable for mass production. General formula A General formula B General formula C
A practical route to quinolines from anilines
Tokuyama, Hidetoshi,Sato, Masashi,Ueda, Toshihiro,Fukuyama, Tohru
, p. 105 - 108 (2007/10/03)
A practical route to quinoline from anilines through acid-mediated cyclization of 3-(N-aryl-N-sulfonylamino)propionaldehydes has been developed. Treatment of the cyclization products, dihydroquinoline intermediates with KOH in DMSO leads to substituted quinolines.
