Tandem One-Pot Synthesis of Indoles Having a Structural Moiety of Propellane

Title:Tandem One-Pot Synthesis of Indoles Having a Structural Moiety of Propellane

Volume: 12 Issue: 3

Author(s): Abdolali Alizadeh, Fahimeh Bayat and Vahideh Sadeghi

Affiliation:

Keywords: Indole, propellane, tryptamin, ninhydrin, one-pot reaction.

Abstract: A concise and efficient route for the synthesis of indole derivatives having propellane structure at position 3 by simple regioselective one-pot reaction of ninhydrin, malononitrile, tryptamine, and β-dicarbonyl compounds was developed. This protocol provides an alternative method for application in combinatorial and parallel synthesis in drug discovery. The value of this method lies in its simplicity, regioselectivity, and good yields. The structures of new synthesized compounds were corroborated spectroscopically (IR, ¹H- and ¹³C-NMR, and EI-MS). A plausible mechanism for this type of reaction is proposed (Scheme 2).

Cite this article as:

Alizadeh Abdolali, Bayat Fahimeh and Sadeghi Vahideh, Tandem One-Pot Synthesis of Indoles Having a Structural Moiety of Propellane, Letters in Organic Chemistry 2015; 12(3) . https://dx.doi.org/10.2174/1570178612666150108003359