Synthesis of 6- or 7-substituted 1,2,3,4-tetrahydroisoquinoline- 3-carboxylic acids
dc.contributor.author | Ma, Wenli | en_US |
dc.contributor.author | Mosberg, Henry I. | en_US |
dc.date.accessioned | 2006-09-08T21:09:00Z | |
dc.date.available | 2006-09-08T21:09:00Z | |
dc.date.issued | 1999-03 | en_US |
dc.identifier.citation | Ma, Wenli; Mosberg, Henry I.; (1999). "Synthesis of 6- or 7-substituted 1,2,3,4-tetrahydroisoquinoline- 3-carboxylic acids." Letters in Peptide Science 6 (2-3): 179-183. <http://hdl.handle.net/2027.42/43174> | en_US |
dc.identifier.issn | 0929-5666 | en_US |
dc.identifier.issn | 1573-3904 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/43174 | |
dc.description.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. | en_US |
dc.format.extent | 50267 bytes | |
dc.format.extent | 3115 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.language.iso | en_US | |
dc.publisher | Kluwer Academic Publishers; Springer Science+Business Media | en_US |
dc.subject.other | Life Sciences | en_US |
dc.subject.other | Polymer Sciences | en_US |
dc.subject.other | Biochemistry, General | en_US |
dc.subject.other | Animal Anatomy / Morphology / Histology | en_US |
dc.subject.other | Amino Acid Synthesis | en_US |
dc.subject.other | Aryl-substitution | en_US |
dc.subject.other | Conformationally Constrained Amino Acids | en_US |
dc.subject.other | Phenylalanine Analogues | en_US |
dc.subject.other | Tetrahydroisoquinoline | en_US |
dc.title | Synthesis of 6- or 7-substituted 1,2,3,4-tetrahydroisoquinoline- 3-carboxylic acids | en_US |
dc.type | Article | en_US |
dc.subject.hlbsecondlevel | Public Health | en_US |
dc.subject.hlbsecondlevel | Biological Chemistry | en_US |
dc.subject.hlbsecondlevel | Chemical Engineering | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbtoplevel | Engineering | en_US |
dc.subject.hlbtoplevel | Health Sciences | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | College of Pharmacy, University of Michigan, Ann Arbor, MI, 48109, U.S.A | en_US |
dc.contributor.affiliationum | College of Pharmacy, University of Michigan, Ann Arbor, MI, 48109, U.S.A | en_US |
dc.contributor.affiliationumcampus | Ann Arbor | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/43174/1/10989_2004_Article_190726.pdf | en_US |
dc.identifier.doi | http://dx.doi.org/10.1023/A:1008826909441 | en_US |
dc.identifier.source | Letters in Peptide Science | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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