Malaysian Journal of Analytical Sciences Vol 25 No 5 (2021): 706 - 715

 

 

 

 

A FACILE SYNTHESIS OF N-ALKYLATED DAIBUCARBOLINE A DERIVATIVES VIA PICTET-SPENGLER CONDENSATION OF TRYPTAMINE

 

(Sintesis Mudah Terbitan Daibukarbolin A Melalui Kondensasi Pictet-Spengler Daripada Triptamin)

 

Nur Ain Nabilah Ash’ari¹, Noor Hidayah Pungot¹*, Zurina Shaameri¹, Nor Akmalazura Jani²

 

¹Organic Synthesis Laboratory, Institute of Science,

Universiti Teknologi MARA, 43200 Bandar Puncak Alam, Selangor, Malaysia

²Faculty of Applied Sciences,

Universiti Teknologi MARA, 72000 Kuala Pilah, Negeri Sembilan, Malaysia

 

*Corresponding author:  noorhidayah977@uitm.edu.my

 

 

Received: 27 July 2021 ; Accepted: 31 August 2021 ; Published:  25 October 2021

 

 

Abstract

A brief and facile approach towards β-carboline and its derivatives is described through a simple three step synthesis. The key reaction involves the construction of β-carboline framework by Pictet-Spengler condensation of tryptamine with various substituted aldehydes. Subsequent aromatization of the resulting tetrahydro-β-carboline intermediates is achieved via iodine-mediated oxidative dehydrogenation reaction.  Thereafter,  insertion of alkyl  subunit at N-1 position  afforded a  series  of  corresponding  N-alkylated β-carboline derivatives. The structures of all synthesized intermediates and derivatives of β-carboline, including three new structures (2k, 2l and 3e), were confirmed by NMR, FTIR and GC-MS spectroscopy.

 

Keywords:  β-carboline, Pictet-Spengler condensation, tetrahydro-β-carboline

 

Abstrak

Pendekatan ringkas dan mudah terhadap β-karbolin dan derivatifnya dijelaskan melalui sintesis tiga langkah mudah. Tindak balas utama melibatkan pembinaan kerangka β-karbolin daripada triptamin melalui kondensasi Pictet-Spengler dengan pelbagai aldehid yang diganti. Aromatisasi seterusnya dari tetrahidro-β-karbolin yang dihasilkan dicapai melalui tindak balas dehidrogenasi oksidatif yang dimediasi iodin. Selepas itu, penyisipan subunit alkil pada kedudukan N-1 menghasilkan satu siri turunan N-alkilasi β-karbolin yang sepadan. Struktur semua perantara yang disintesis dan turunan β-karbolin disahkan oleh spektroskopi NMR, FTIR dan GC-MS dan tiga kompaun (2k, 2l, dan 3e) adalah baru.

 

Kata kunci:  β-karbolin, kondensasi Pictet-Spengler, tetrahidro-β-karbolin

 

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