Synthetic Studies in β - Arylethylomine Derivatives

Pradhan, Prasun K (2006) Synthetic Studies in β - Arylethylomine Derivatives. PhD thesis, Jadavpur University.


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    Giri, V S


    The Pictet - Spengler reaction (PS)1 is one of the most important and widely used reaction for the synthesis of both isoquinoline and indole alkaloids. This reaction was discovered in 1911 by Ame Pictet and Theodor Spengler2 when they condensed phenethylamine (1) with methylal (2) in presence of hydrochloric acid3 to provide 1 - methyl 1, 2, 3, 4 - tetrahydroisoquinolines (3). This reaction was initially used for synthesizing tetrahydroisoquinolines (THIQ; 5). It was later modified to obtain other β- phenethylamines such as N - alkyl, N - acyl and N - sulphonyl derivatives, proceeding via the corresponding iminium ion (4) or enaminones3c followed by intramolecular electrophilic substitution/cyclization as depicted in Scheme 1. The reaction was subsequently used as standard method for preparing tetrahydroisoquinolines (THIQ).

    Item Type: Thesis (PhD)
    Subjects: Chemistry
    Divisions: Indian Institute of Chemical Biology
    Depositing User: Mr Santanu Sadhukhan
    Date Deposited: 24 Nov 2011 14:10
    Last Modified: 28 Oct 2013 16:15

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