Synthetic Studies in β - Arylethylomine Derivatives
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
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| Title |
Synthetic Studies in β - Arylethylomine Derivatives
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| Creator |
Pradhan, Prasun K
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| Subject |
Chemistry
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| Description |
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).
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| Date |
2006
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| Type |
Thesis
NonPeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://www.eprints.iicb.res.in/653/1/thesis_in_one.pdf
Pradhan, Prasun K (2006) Synthetic Studies in β - Arylethylomine Derivatives. PhD thesis, Jadavpur University. |
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| Relation |
http://www.eprints.iicb.res.in/653/
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