Synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives by cycloaddition approaches
DSpace at IIT Bombay
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Title |
Synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives by cycloaddition approaches
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Creator |
KOTHA, S
SREENIVASACHARY, N |
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Subject |
alpha-amino-acids
ring-closing metathesis solid-phase synthesis asymmetric-synthesis organic-synthesis alpha,beta-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid nickel(0)-catalyzed -cocyclization isoquinoline derivatives constrained analogs olefin metathesis amino acids combinatorial chemistry drug design metathesis peptides peptidomimetics |
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Description |
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 alpha -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 exocyclic dienes 26 and 29, the key steps being an enyne metathesis reaction and cycloisomerization. Various topographically constrained Tic derivatives have been synthesized using dienes containing an alpha -amino acid moiety through Diels-Alder reactions. For the first time, [2+2+2] cyclotrimerization, as promoted by Wilkinson's and Vollhardt's catalysts, has been used for the synthesis of various highly functionalized Tic derivatives.
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Publisher |
WILEY-V C H VERLAG GMBH
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Date |
2011-09-01T21:25:49Z
2011-12-26T12:59:48Z 2011-12-27T05:52:41Z 2011-09-01T21:25:49Z 2011-12-26T12:59:48Z 2011-12-27T05:52:41Z 2001 |
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Type |
Article
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Identifier |
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (17), 3375-3383
1434-193X http://dspace.library.iitb.ac.in/xmlui/handle/10054/12872 http://hdl.handle.net/10054/12872 |
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Language |
en
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