Efficient synthesis of 1,4-dihydro-2H-isoquinoline-3,5,8-triones via cyclobutene ring expansion

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6881-6887

  Wipf, Peter ^a   Hopkins, Corey R ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDRO 2H ISOQUINOLINE 3,5,8 TRIONE; HETEROCYCLIC COMPOUND; ISOQUINOLINE DERIVATIVE; NATURAL PRODUCT; SQUARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NOTE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032888526     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990089v     Document Type: Note

References (27)

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11. Amide 6a was obtained in 84% yield.
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13. Squarates 3b and 3d were prepared in two steps from the commercially available diisopropoxy squarate according to ref 8.
14. 3) in 54% overall yield from 2a. Formula Represented
15. However, use of an N-methyl group in place of the N-benzyl function in 2a provided equivalent yields in the ring-opening rearrangement reaction.
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18. Wipf, P.; Uto, Y. Unpublished results.
19. The irons-amide conformation shown for 7e is favored by ca. 2 kcal/mol over the cis conformation according to MacroModel MM2* calculations. In contrast, the trans-amide conformation shown for 7f is favored by ca. 9 kcal/mol.
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