AI Article Synopsis
- A highly efficient synthesis of 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines was achieved using a Pictet-Spengler reaction involving arylethylamines and ketones.
- The reaction utilized titanium (IV) isopropoxide and acetic-formic anhydride, enhancing the formation of the acyliminium ion.
- Trifluoroacetic acid was used as an additional reagent to facilitate cyclization, making the procedure convenient and effective for producing these compounds in a single pot.
Article Abstract
A synthesis of 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines (6) was achieved in a highly efficient manner via Pictet-Spengler reaction of arylethylamines (1) and acyclic and cyclic ketones (2) using titanium (IV) isopropoxide and acetic-formic anhydride. The cyclization of the in situ formed acyliminium ion (4) to N-formyl 1,2,3,4-tetrahydroisoquinoline (5) was greatly facilitated by using trifluoroacetic acid as an additional reagent. The Pictet-Spengler reaction was carried out by one pot procedure, providing a convenient and effective method for preparing various 1,2,3,4-tetrahydroisoquinolines.
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| http://dx.doi.org/10.1248/cpb.50.253 | DOI Listing |
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