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- Title
Experimental and Theoretical Observations on the Intramolecular Nucleophilic Addition of α-Amino Carbanions to Arynes: Synthesis of 1-Aryl-1,2,3,4-tetrahydroisoquinolines.
- Authors
Kaur, Manjot; Sharma, Esha; Singh, Amritpal; Singh, Paramjit; Singh, Kamal Nain
- Abstract
1-Aryl-1,2,3,4-tetrahydroisoquinolines (THIQ) are key intermediates and products in the pharmaceutical industry. A new method involving intramolecular nucleophilic addition of α-amino carbanions to in-situ-generated arynes in N-Boc-protected (Boc = tert-butoxycarbonyl) amine substrates is presented for the synthesis of these compounds. Surprisingly, a similar reaction in Lewis-acid-complexed tertiary amines failed. These results have been analysed using quantum chemical calculations on the intermediates involved in the reactions.
- Subjects
CARBANIONS; IONS; CARBANION compounds; TETRAHYDROISOQUINOLINES; HETEROCYCLIC compounds
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 24, p4159
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600567