Abstract:This study presents a convenient synthesis of pyrrolo[1,2-a]quinolines and pyrrolo[2,1-a]isoquinolines with simple quinolines or isoquinolines and Morita−Baylis−Hillman carbonates in the presence of copper acetate. A range of functionalized benzoindolizines could be assembled through an S N 2′/deprotonation/1,5-electrocyclization/oxidation cascade pathway in a one-step process.
“…All reagents and solvents were obtained from commercial sources and used without further purification. Compound 1 and 4 were prepared according to our reported procedure …”
Section: Methodsmentioning
confidence: 99%
“…In addition, the combination of bromoisobutyrate and dimethyl sulfoxide can also act as the bromination reagent if pyrroloisoquinolines without a methoxy group are employed. Here, we present our development of formylation and bromination of pyrroloisoquinolines using bromoisobutyrate and dimethyl sulfoxide …”
We have developed an efficient formylation
of pyrroloisoquinolines
using bromoisobutyrate and dimethyl sulfoxide as carbonyl reagent.
Various formylated pyrroloisoquinolines could be prepared in good
yields (up to 94%). This formylation process can be easily scaled
up to gram scale with good yield. In most cases of pyrroloisoquinolines
without methoxy groups, the combination of bromoisobutyrate and dimethyl
sulfoxide could act as a bromination reagent, delivering brominated
pyrroloisoquinolines in acceptable to good yields (up to 82%).
“…All reagents and solvents were obtained from commercial sources and used without further purification. Compound 1 and 4 were prepared according to our reported procedure …”
Section: Methodsmentioning
confidence: 99%
“…In addition, the combination of bromoisobutyrate and dimethyl sulfoxide can also act as the bromination reagent if pyrroloisoquinolines without a methoxy group are employed. Here, we present our development of formylation and bromination of pyrroloisoquinolines using bromoisobutyrate and dimethyl sulfoxide …”
We have developed an efficient formylation
of pyrroloisoquinolines
using bromoisobutyrate and dimethyl sulfoxide as carbonyl reagent.
Various formylated pyrroloisoquinolines could be prepared in good
yields (up to 94%). This formylation process can be easily scaled
up to gram scale with good yield. In most cases of pyrroloisoquinolines
without methoxy groups, the combination of bromoisobutyrate and dimethyl
sulfoxide could act as a bromination reagent, delivering brominated
pyrroloisoquinolines in acceptable to good yields (up to 82%).
“…Functionalized ynone 2 a was used for a reaction with isoquinoline 1 a (Table 1). [15] To our delight, the desired imidazo[2,3‐ a ]isoquinoline 3 a can be isolated in 36% yield by stirring the reaction mixture at rt for 23 h (entry 1). The stereochemistry of compound 3 a was confirmed by X‐ray single crystal analysis [16] .…”
A mild dearomatization/annulation cascade sequence of isoquinolines and quinolines with ynones has been developed. Highly functionalized imidazo[2,3‐a]isoquinoline and imidazo[3,2‐a]quinoline derivatives could be prepared directly in moderate to excellent yields.
“…The mechanism of the last key step relies on the formation of vinylpyridinium ylides which are prone toward 1,5-electrocyclization. 65,66 The initially formed dihydroindolizine eliminates NO 2 − and furnishes the final aromatic product. The trouble with Kröhnke's approach is that it is mostly limited to explosive 1-chloro-2,4,6-trinitrobenzene.…”
Benzo[a]indolizines with an ordered arrangement of various electron-withdrawing substituents (NO2, CF3, CN, CO2R and COPh) were prepared directly from pyridinium salts and chloronitroarenes, allowing for refined control of the photophysical...
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