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Synthesis of 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid (Tic) Derivatives by Cycloaddition Approaches

โœ Scribed by Sambasivarao Kotha; Nampally Sreenivasachary

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
396 KB
Volume
2001
Category
Article
ISSN
1434-193X

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โœฆ Synopsis

A new and general synthetic methodology for the preparation of functionalized 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives by a cycloaddition strategy is described. The synthesis of various enyne building blocks 12, 13, 21, and 22 containing an ฮฑ-amino acid moiety using Schiff base 8 as a glycine equivalent has been achieved under mild reaction conditions. These building blocks have been utilized in the synthesis of inner-outer ring dienes 23 and 24 and ex- [ โ€ก] N.

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## Abstract The reaction of Nโ€arylโ€Cโ€ethoxycarbonyl nitrilimines with [1,2,4]triazepinโ€3,5โ€dithione leads to title compounds. The 1,3โ€dipolar cycloaddition is completely peri and regioselective. The preferred orientation of addition is predicted correctly by AM~1~ calculation.