ISSN:
1573-3904
Keywords:
amino acid synthesis
;
aryl-substitution
;
conformationally constrained amino acids
;
phenylalanine analogues
;
tetrahydroisoquinoline
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract A straightforward approach for the synthesis of several new, aryl-substituted derivatives of the conformationally constrained phenylalanine analogue 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) is described. Tic, nitro-substituted at the 6 or 7 position, was prepared by base-catalyzed cyclization of diethyl acetamidomalonate with α,α-dibromo-4-nitro-o- xylene followed by decarboxylation and deacylation under refluxing conditions in aqueous HCl. Catalytic hydrogenation of nitro-Tic in the presence of 10% Pd/C afforded amino-Tic, which was then converted to iodo-Tic by a modified Sandmeyer reaction. Both amino- Tic and iodo-Tic can easily be transformed to other substituents.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1008826909441
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