Tetrahedron

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)- …

P Kothandaraman, SJL Lauw, PWH Chan

Index: Kothandaraman, Prasath; Lauw, Sherman Jun Liang; Chan, Philip Wai Hong Tetrahedron, 2013 , vol. 69, # 35 p. 7471 - 7480

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Citation Number: 7

Abstract

Abstract 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 yields (48–91%) from a wide range of alcohol substrates that are low cost, easily accessible, and ecologically benign. The utility of the approach as a potential scale-up ...