1984
DOI: 10.1016/s0040-4039(01)81195-3
|View full text |Cite
|
Sign up to set email alerts
|

An unusual rearrangement during pyridine synthesis. Anomalous condensation of a β-keto enamine with a tetronic acid.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

0
2
0

Year Published

1984
1984
2007
2007

Publication Types

Select...
3
2

Relationship

0
5

Authors

Journals

citations
Cited by 5 publications
(2 citation statements)
references
References 9 publications
0
2
0
Order By: Relevance
“…The unanticipated benzyl deprotection is likely due to activation of the aryl benzyl ether oxygen followed by nucleophilic cleavage of the benzyl group. 10 Amide 20 was generated through a two-step process, avoiding activation of the carbonyl. Esterification of 19 followed by treatment with BuLi and anhydrous NH 3 gave the key amide 20.…”
mentioning
confidence: 99%
See 1 more Smart Citation
“…The unanticipated benzyl deprotection is likely due to activation of the aryl benzyl ether oxygen followed by nucleophilic cleavage of the benzyl group. 10 Amide 20 was generated through a two-step process, avoiding activation of the carbonyl. Esterification of 19 followed by treatment with BuLi and anhydrous NH 3 gave the key amide 20.…”
mentioning
confidence: 99%
“…Attempts to directly convert the acid into amide 20 via formation of an activated ester were unsuccessful, leading to exclusive formation of lactone 21 . The unanticipated benzyl deprotection is likely due to activation of the aryl benzyl ether oxygen followed by nucleophilic cleavage of the benzyl group . Amide 20 was generated through a two-step process, avoiding activation of the carbonyl.…”
mentioning
confidence: 99%