dc.contributor.author |
KUMAR, MOTHUKURI GANESH |
en_US |
dc.contributor.author |
VEERESH, KURUVA |
en_US |
dc.contributor.author |
NALAWADE, SACHIN A. |
en_US |
dc.contributor.author |
NITHUN, RAJ V. |
en_US |
dc.contributor.author |
GOPI, HOSAHUDYA N. |
en_US |
dc.date.accessioned |
2020-01-01T05:03:27Z |
|
dc.date.available |
2020-01-01T05:03:27Z |
|
dc.date.issued |
2019-10 |
en_US |
dc.identifier.citation |
Journal of Organic Chemistry, 84(23), 15145-15153. |
en_US |
dc.identifier.issn |
0022-3263 |
en_US |
dc.identifier.issn |
1520-6904 |
en_US |
dc.identifier.uri |
http://dr.iiserpune.ac.in:8080/xmlui/handle/123456789/4317 |
|
dc.identifier.uri |
https://doi.org/10.1021/acs.joc.9b01936 |
en_US |
dc.description.abstract |
Here, we are reporting a single-step transformation of N-protected α,β-unsaturated γ-amino amides into 5,5-disubstituted γ-lactams through a base-mediated new molecular rearrangement. In contrast to the known N- to C(O) cyclization of saturated γ-amino acids into corresponding γ-lactams, the new rearrangement involves the cyclization between N-terminal Cγ- to C-terminal amide N. The cyclization process was initiated by the migration of double bond from α,β → β,γ position. The enamine–imine tautomerization of the new β,γ-double bond and subsequent 5-exo-trig cyclization of terminal amide leads to the formation of N-protected 5,5-disubstituted γ-lactam. The structures of various γ-lactams obtained from the rearrangement were studied in single crystals. Overall, the results reported here demonstrate the facile and single-step transformation of N-protected α,β-unsaturated γ-amino amides into γ-lactams and provided an excellent opportunity to construct small-molecule peptidomimetics. |
en_US |
dc.language.iso |
en |
en_US |
dc.publisher |
American Chemical Society |
en_US |
dc.subject |
Stereoselective-Synthesis |
en_US |
dc.subject |
Biological Evaluation |
en_US |
dc.subject |
Structural Features |
en_US |
dc.subject |
Inhibitors |
en_US |
dc.subject |
Discovery |
en_US |
dc.subject |
Antibiotics |
en_US |
dc.subject |
Cyclization |
en_US |
dc.subject |
Helices |
en_US |
dc.subject |
Design |
en_US |
dc.subject |
Alpha |
en_US |
dc.subject |
TOC-DEC-2019 |
en_US |
dc.subject |
2019 |
en_US |
dc.title |
Direct Transformation of N Protected alpha beta Unsaturated gamma Amino Amides into gamma Lactams through a Base Mediated Molecular Rearrangement |
en_US |
dc.type |
Article |
en_US |
dc.contributor.department |
Dept. of Chemistry |
en_US |
dc.identifier.sourcetitle |
Journal of Organic Chemistry |
en_US |
dc.publication.originofpublisher |
Foreign |
en_US |