1448531-98-3Relevant academic research and scientific papers
Tandem Cu-catalyzed ketenimine formation and intramolecular nucleophile capture: Synthesis of 1,2-dihydro-2-iminoquinolines from 1-(o-acetamidophenyl) propargyl alcohols
Kumar, Gadi Ranjith,Kumar, Yalla Kiran,Kant, Ruchir,Reddy, Maddi Sridhar
supporting information, p. 1255 - 1260 (2014/06/24)
The copper-catalyzed ketenimine formation reaction of 1-(o-acetamidophenyl) propargyl alcohols with various sulfonyl azides is found to undergo a concomitant intramolecular nucleophile attack to generate 1,2-dihydro-2- iminoquinolines after aromatization (via elimination of acetyl and hydroxy groups) and tautomerization. The reaction produces 4-substituted and 3,4-unsubstituted title compounds in moderate to good yields under mild reaction conditions.
1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis
Kothandaraman, Prasath,Koh, Bing Qin,Limpanuparb, Taweetham,Hirao, Hajime,Chan, Philip Wai Hong
supporting information, p. 1978 - 1985 (2013/03/14)
A synthetic method that relies on NIS (N-iodosuccinimide)-mediated cycloisomerization reactions of 1-(2′-anilinyl)prop-2-yn-1-ols to gem-3-(diiodomethyl)indolin-2-ones and 2-(iodomethylene)indolin-3-ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3- and 2-oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2-OH and 1,2-alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity. Copyright
Metal-free synthesis of 1H-indole-2-carbaldehydes by N-iodosuccinimide- mediated cyclization of 1-(2′-anilinyl)prop-2-yn-1-ols in water. A formal synthesis of (R)-calindol
Kothandaraman, Prasath,Lauw, Sherman Jun Liang,Chan, Philip Wai Hong
, p. 7471 - 7480 (2013/08/23)
A N-iodosuccinimide (NIS)-mediated method to prepare 1H-indole-2- carbaldehydes efficiently from cycloisomerization of 1-(2-aminophenyl)prop-2-yn- 1-ols is described. The reaction is operationally straightforward and accomplished in good to excellent yiel
