245-33-0Relevant academic research and scientific papers
Aryne [3 + 2] cycloaddition with N-sulfonylpyridinium imides and in situ generated N-sulfonylisoquinolinium imides: A potential route to pyrido[1,2-b]indazoles and indazolo[3,2-a]isoquinolines
Zhao, Jingjing,Li, Pan,Wu, Chunrui,Chen, Hongli,Ai, Wenying,Sun, Renhong,Ren, Hailong,Larock, Richard C.,Shi, Feng
scheme or table, p. 1922 - 1930 (2012/04/23)
The aryne [3 + 2] cycloaddition process with pyridinium imides breaks the aromaticity of the pyridine ring. By equipping the imide nitrogen with a sulfonyl group, the intermediate readily eliminates a sulfinate anion to restore the aromaticity, leading to the formation of pyrido[1,2-b]indazoles. The scope and limitation of this reaction are discussed. As an extension of this chemistry, N-tosylisoquinolinium imides, generated in situ from N′-(2-alkynylbenzylidene)-tosylhydrazides via an AgOTf-catalyzed 6-endo-dig electrophilic cyclization, readily undergo aryne [3 + 2] cycloaddition to afford indazolo[3,2-a]-isoquinolines in the same pot, offering a highly efficient route to these potential anticancer agents.
Synthesis of pyrido[1,2-b]indazoles via aryne [3+2] cycloaddition with N-tosylpyridinium imides
Zhao, Jingjing,Wu, Chunrui,Li, Pan,Ai, Wenying,Chen, Hongli,Wang, Chaojie,Larock, Richard C.,Shi, Feng
scheme or table, p. 6837 - 6843 (2011/10/04)
The [3 + 2] cycloaddition of arynes with N-tosylpyridinium imides, followed by an elimination of Ts-, affords pyrido[1,2-b]indazoles under mild reaction conditions in good yields.
REACTIONS OF SUBSTITUTED PYRIDINIUM N-IMINES WITH BENZYNE: SYNTHESES OF PYRIDOINDAZOLES AND RELATED COMPOUNDS
Yamashita, Yoshiro,Hayashi, Takashi,Masumura, Mitsuo
, p. 1133 - 1136 (2007/10/02)
Reactions of benzyne with several pyridinium N-imines were examined. 2-o-Aminophenylpyridine derivatives 6, pyridoindazoles (7), indazoloquinoline (17), and indazoloisoquinoline (18) were obtained by the reactions of benzyne with the
