[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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Bibliographic Details
Published inOrganic letters Vol. 21; no. 7; pp. 2312 - 2316
Main Authors Zeng, Rong, Shan, Changyu, Liu, Ming, Jiang, Kun, Ye, Ying, Liu, Tian-Yu, Chen, Ying-Chun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.04.2019
Amer Chemical Soc
Subjects
chemical structure
Chemistry
Chemistry, Organic
cyclization reactions
Physical Sciences
pyridines
Science & Technology
ORGANOCATALYTIC CYCLOPROPANATION
MEDIATED CYCLOPROPANATION
CYCLOADDITION
HETEROCYCLES
CONSTRUCTION
AMMONIUM YLIDES
LEAVING GROUP
PYRIDINES
3-EXO-TET CYCLIZATION
1,3-DIHALOPROPANES
Online AccessGet full text
ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.9b00598

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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.9b00598