[4 + 1 + 1] Annulations of α‑Bromo Carbonyls and 1‑Azadienes toward Fused Benzoazaheterocycles
An unexpected [4 + 1 + 1] annulation between α-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2H)-ones or 2-methylenebenzo[b]thiophene-3(2H)-ones, has been observed in the presence of DABCO and Cs2CO3. These reactions stand in contrast to the common [4 + 1] cyclization rea...
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| Published in | Organic letters Vol. 21; no. 7; pp. 2312 - 2316 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
05.04.2019
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1523-7060 1523-7052 1523-7052 |
| DOI | 10.1021/acs.orglett.9b00598 |
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| Abstract | An unexpected [4 + 1 + 1] annulation between α-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2H)-ones or 2-methylenebenzo[b]thiophene-3(2H)-ones, has been observed in the presence of DABCO and Cs2CO3. These reactions stand in contrast to the common [4 + 1] cyclization reactions of azadienes with the related sulfonium ylides. A range of fused benzofuro[3,2-b]pyridines and benzo[4,5]thieno[3,2-b]pyridines have been efficiently constructed in fair to excellent yields. |
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| AbstractList | An unexpected [4 + 1 + 1] annulation between α-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2 H)-ones or 2-methylenebenzo[ b]thiophene-3(2 H)-ones, has been observed in the presence of DABCO and Cs
CO
. These reactions stand in contrast to the common [4 + 1] cyclization reactions of azadienes with the related sulfonium ylides. A range of fused benzofuro[3,2- b]pyridines and benzo[4,5]thieno[3,2- b]pyridines have been efficiently constructed in fair to excellent yields. An unexpected [4 + 1 + 1] annulation between α-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2H)-ones or 2-methylenebenzo[b]thiophene-3(2H)-ones, has been observed in the presence of DABCO and Cs2CO3. These reactions stand in contrast to the common [4 + 1] cyclization reactions of azadienes with the related sulfonium ylides. A range of fused benzofuro[3,2-b]pyridines and benzo[4,5]thieno[3,2-b]pyridines have been efficiently constructed in fair to excellent yields. An unexpected [4 + 1 + 1] annulation between alpha-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2H)-ones or 2-methylenebenzo[b]thiophene-3(2H)-ones, has been observed in the presence of DABCO and Cs2CO3. These reactions stand in contrast to the common [4 + 1] cyclization reactions of azadienes with the related sulfonium ylides. A range of fused benzofuro[3,2-b]pyridines and benzo[4,5]thieno[3,2-b]pyridines have been efficiently constructed in fair to excellent yields. An unexpected [4 + 1 + 1] annulation between α-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2H)-ones or 2-methylenebenzo[b]thiophene-3(2H)-ones, has been observed in the presence of DABCO and Cs₂CO₃. These reactions stand in contrast to the common [4 + 1] cyclization reactions of azadienes with the related sulfonium ylides. A range of fused benzofuro[3,2-b]pyridines and benzo[4,5]thieno[3,2-b]pyridines have been efficiently constructed in fair to excellent yields. |
| Author | Shan, Changyu Liu, Ming Ye, Ying Chen, Ying-Chun Zeng, Rong Liu, Tian-Yu Jiang, Kun |
| AuthorAffiliation | Department of Medicinal Chemistry, West China School of Pharmacy College of Pharmacy |
| AuthorAffiliation_xml | – name: Department of Medicinal Chemistry, West China School of Pharmacy – name: College of Pharmacy |
| Author_xml | – sequence: 1 givenname: Rong surname: Zeng fullname: Zeng, Rong organization: College of Pharmacy – sequence: 2 givenname: Changyu surname: Shan fullname: Shan, Changyu organization: College of Pharmacy – sequence: 3 givenname: Ming surname: Liu fullname: Liu, Ming organization: College of Pharmacy – sequence: 4 givenname: Kun surname: Jiang fullname: Jiang, Kun email: kjiang125@hotmail.com organization: College of Pharmacy – sequence: 5 givenname: Ying surname: Ye fullname: Ye, Ying organization: College of Pharmacy – sequence: 6 givenname: Tian-Yu surname: Liu fullname: Liu, Tian-Yu organization: College of Pharmacy – sequence: 7 givenname: Ying-Chun orcidid: 0000-0003-1902-0979 surname: Chen fullname: Chen, Ying-Chun email: ycchen@scu.edu.cn organization: Department of Medicinal Chemistry, West China School of Pharmacy |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30900459$$D View this record in MEDLINE/PubMed |
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| Keywords | ORGANOCATALYTIC CYCLOPROPANATION MEDIATED CYCLOPROPANATION CYCLOADDITION HETEROCYCLES CONSTRUCTION AMMONIUM YLIDES LEAVING GROUP PYRIDINES 3-EXO-TET CYCLIZATION 1,3-DIHALOPROPANES |
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| Snippet | An unexpected [4 + 1 + 1] annulation between α-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2H)-ones or... An unexpected [4 + 1 + 1] annulation between alpha-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2H)-ones or... An unexpected [4 + 1 + 1] annulation between α-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2 H)-ones or 2-methylenebenzo[... An unexpected [4 + 1 + 1] annulation between α-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2H)-ones or... |
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| Title | [4 + 1 + 1] Annulations of α‑Bromo Carbonyls and 1‑Azadienes toward Fused Benzoazaheterocycles |
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