Unique Tandem Heck-Lactamization Naphthyridinone Ring Formation between Acrylanilides and Halogenated Pyridines
The Heck coupling of acrylanilides with 4-bromo-2-chloro-3-iodo-pyridine using palladium acetate can produce bis-Heck products or undergo an unusual tandem Heck-lactamization ring formation to generate 5-chloro-1-aryl-1,6-naphthyridin-2(1H)-ones.
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| Published in | Journal of organic chemistry Vol. 71; no. 22; pp. 8610 - 8613 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
27.10.2006
Amer Chemical Soc |
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| Abstract | The Heck coupling of acrylanilides with 4-bromo-2-chloro-3-iodo-pyridine using palladium acetate can produce bis-Heck products or undergo an unusual tandem Heck-lactamization ring formation to generate 5-chloro-1-aryl-1,6-naphthyridin-2(1H)-ones. |
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| AbstractList | The Heck coupling of acrylanilides with 4-bromo-2-chloro-3-iodo-pyridine using palladium acetate can produce bis-Heck products or undergo an unusual tandem Heck-lactamization ring formation to generate 5-chloro-1-aryl-1,6-naphthyridin-2(1H)-ones. |
| Author | Chilenski, Jennifer R DiMichele, Lisa Cvetovich, Raymond J Chung, John Y. L Reamer, Robert A |
| Author_xml | – sequence: 1 givenname: Raymond J surname: Cvetovich fullname: Cvetovich, Raymond J – sequence: 2 givenname: Robert A surname: Reamer fullname: Reamer, Robert A – sequence: 3 givenname: Lisa surname: DiMichele fullname: DiMichele, Lisa – sequence: 4 givenname: John Y. L surname: Chung fullname: Chung, John Y. L – sequence: 5 givenname: Jennifer R surname: Chilenski fullname: Chilenski, Jennifer R |
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| Cites_doi | 10.1021/jo049149+ 10.1021/op060125+ 10.1021/ol049165t 10.1016/j.tetlet.2004.03.162 10.1021/ol025950z 10.1021/jo034805b 10.1021/cr000241p 10.1016/j.bmcl.2005.09.065 10.1021/jo0514927 10.1055/s-1974-23300 10.1021/jo00358a003 10.1021/jo00079a031 10.3184/030823402103170367 10.1016/S0022-328X(01)00967-6 10.1016/S0960-894X(02)00990-3 10.1002/adsc.200202180 10.1016/S0040-4020(01)80859-0 10.1080/00397919008051600 10.3184/030823402103171320 10.1021/jo00110a050 10.1021/jm00119a010 10.1002/jhet.5570380505 10.1016/0040-4020(96)00266-9 |
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| Keywords | QUINOLINONES INHIBITORS Nitrogen heterocycle Heck reaction Transition metal Organic bromine compounds Palladium Tandem reaction Organic chlorine compounds Organic halogen compounds Pyridine derivatives Organic iodine compounds Aromatic compound Naphtyridine derivatives Platinoid |
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| Snippet | The Heck coupling of acrylanilides with 4-bromo-2-chloro-3-iodo-pyridine using palladium acetate can produce bis-Heck products or undergo an unusual tandem... |
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| SubjectTerms | Anilides - chemistry Chemistry Chemistry, Organic Cyclization Exact sciences and technology Halogens - chemistry Halogens - metabolism Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Lactams - chemistry Molecular Structure Naphthyridines - chemistry Organic chemistry Palladium - chemistry Physical Sciences Preparations and properties Pyridines - chemistry Pyridines - metabolism Science & Technology |
| Title | Unique Tandem Heck-Lactamization Naphthyridinone Ring Formation between Acrylanilides and Halogenated Pyridines |
| URI | http://dx.doi.org/10.1021/jo0613479 https://api.istex.fr/ark:/67375/TPS-8VRLHWJG-9/fulltext.pdf http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000241435600038 https://www.ncbi.nlm.nih.gov/pubmed/17064040 https://search.proquest.com/docview/68997667 |
| Volume | 71 |
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