Cyclization of lithiated pyridine and quinoline carboxamides: Synthesis of partially saturated pyrrolopyridines and spirocyclic β-lactams

Organic Letters

Volumn 7, Issue 17, 2005, Pages 3673-3676

  Clayden, Jonathan ^a   Hamilton, Stuart D ^a   Mohammed, Rukhsana T ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; LITHIUM; PYRIDINE DERIVATIVE; PYRROLE DERIVATIVE; QUINOLINE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

BETA-LACTAMS; CYCLIZATION; LITHIUM; MOLECULAR STRUCTURE; PYRIDINES; PYRROLES; QUINOLINES; SPIRO COMPOUNDS;

EID: 24044516515     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051214u     Document Type: Article

References (40)

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23. As with most of the reactions described in this paper, use of fewer equivalents of LDA led to incomplete reaction.
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25. Clayden, J.; Knowles, F. E.; Menet, C. J. Synlett 2003, 1701) . It seems that the organolithium always prefers to attack ortho rather than para to a π donating group such as OMe, presumably because at the ortho position inductive σ electron withdrawal at least partially counterbalances the increased π electron density.
26. We have proposed that related cyclizations are electrocyclic ring closures (see: Clayden, J.; Purewal, S.; Helliwell, M.; Mantell, S. J. Angew. Chem., Int. Ed. 2002, 41, 1049)
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30. Lack of stereoselectivity in the formation of 13 suggests that 12 is formed with lower diastereoselectivity than 3. The two regioisomers 14 each appeared to be a single diastereoisomer, however, suggesting that the regioselectivity of protonation may be dependent on stereochemistry. Stereochemistries of 13 were not determined unequivocally and are assigned by analogy with ref 3.
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