11 research outputs found
Synthesis of Tetrahydro‑1<i>H</i>‑indeno[1,2‑<i>b</i>]pyridine via Cascade Cyclization and Friedel–Crafts Reaction
A convenient protocol
has been established for the synthesis of
1-tosyl-2,3,4,5-tetrahydro-1<i>H</i>-indenoÂ[1,2-<i>b</i>]Âpyridine via cascade cyclization and Friedel–Crafts
reaction of 4-methyl-<i>N</i>-(pent-4-yn-1-yl)Âbenzenesulfonamides
and aldehydes in good yields. The methodology has been used for the
total synthesis of the antidepressant agent (±)-5-phenyl-2,3,4,4a,5,9b-hexahydro-1<i>H</i>-indenoÂ[1,2-<i>b</i>]Âpyridine
Stereoselective Synthesis of Amido and Phenyl Azabicyclic Derivatives via a Tandem Aza Prins-Ritter/Friedel–Crafts Type Reaction of Endocyclic <i>N</i>‑Acyliminium Ions
A simple protocol is described for
the synthesis of amido and phenyl
hexahydroindolizin-3Â(2<i>H</i>)-one, hexahydro-1<i>H</i>-quinolizin-4Â(6<i>H</i>)-one, and 1,3,4,10<i>b</i>-tetrahydropyridoÂ[2,1<i>-a</i>]Âisoindol-6Â(2<i>H</i>)-one derivatives via endo-trig (aza-Prins type) cyclization
followed by an intermolecular Ritter/Friedel–Crafts reaction
of cyclic <i>N</i>-acyliminium ions, which are derived from
the boron trifluoride etherate treatment of regioselectively reduced <i>N</i>-homoallyl imides. The reactions are highly diastereoselective
with excellent yields
Synthesis of Tetrahydro‑1<i>H</i>‑indeno[1,2‑<i>b</i>]pyridine via Cascade Cyclization and Friedel–Crafts Reaction
A convenient protocol
has been established for the synthesis of
1-tosyl-2,3,4,5-tetrahydro-1<i>H</i>-indenoÂ[1,2-<i>b</i>]Âpyridine via cascade cyclization and Friedel–Crafts
reaction of 4-methyl-<i>N</i>-(pent-4-yn-1-yl)Âbenzenesulfonamides
and aldehydes in good yields. The methodology has been used for the
total synthesis of the antidepressant agent (±)-5-phenyl-2,3,4,4a,5,9b-hexahydro-1<i>H</i>-indenoÂ[1,2-<i>b</i>]Âpyridine
Diastereoselective Synthesis of Dihydropyrans via Prins Cyclization of Enol Ethers: Total Asymmetric Synthesis of (+)-Civet Cat Compound
Trimethylsilyl
trifluoromethanesulfonate (TMSOTf) can be efficiently
used for Prins cyclization of acrylyl enol ethers to 5,6-dihydro-2<i>H</i>-pyran-2-acetates stereo- and regioselectively in good
yields. The methodology was used for the total synthesis of natural
product (+)-civet
Diastereoselective Synthesis of Dihydropyrans via Prins Cyclization of Enol Ethers: Total Asymmetric Synthesis of (+)-Civet Cat Compound
Trimethylsilyl
trifluoromethanesulfonate (TMSOTf) can be efficiently
used for Prins cyclization of acrylyl enol ethers to 5,6-dihydro-2<i>H</i>-pyran-2-acetates stereo- and regioselectively in good
yields. The methodology was used for the total synthesis of natural
product (+)-civet
Stereoselective Synthesis of Amido and Phenyl Azabicyclic Derivatives via a Tandem Aza Prins-Ritter/Friedel–Crafts Type Reaction of Endocyclic <i>N</i>‑Acyliminium Ions
A simple protocol is described for
the synthesis of amido and phenyl
hexahydroindolizin-3Â(2<i>H</i>)-one, hexahydro-1<i>H</i>-quinolizin-4Â(6<i>H</i>)-one, and 1,3,4,10<i>b</i>-tetrahydropyridoÂ[2,1<i>-a</i>]Âisoindol-6Â(2<i>H</i>)-one derivatives via endo-trig (aza-Prins type) cyclization
followed by an intermolecular Ritter/Friedel–Crafts reaction
of cyclic <i>N</i>-acyliminium ions, which are derived from
the boron trifluoride etherate treatment of regioselectively reduced <i>N</i>-homoallyl imides. The reactions are highly diastereoselective
with excellent yields
Synthesis of Tetrahydro‑1<i>H</i>‑indeno[1,2‑<i>b</i>]pyridine via Cascade Cyclization and Friedel–Crafts Reaction
A convenient protocol
has been established for the synthesis of
1-tosyl-2,3,4,5-tetrahydro-1<i>H</i>-indenoÂ[1,2-<i>b</i>]Âpyridine via cascade cyclization and Friedel–Crafts
reaction of 4-methyl-<i>N</i>-(pent-4-yn-1-yl)Âbenzenesulfonamides
and aldehydes in good yields. The methodology has been used for the
total synthesis of the antidepressant agent (±)-5-phenyl-2,3,4,4a,5,9b-hexahydro-1<i>H</i>-indenoÂ[1,2-<i>b</i>]Âpyridine
Synthesis of Five‑, Six‑, and Seven-Membered 1,3- and 1,4-Heterocyclic Compounds via Intramolecular Hydroalkoxylation/Hydrothioalkoxylation of Alkenols/Thioalkenols
Intramolecular
hydroalkoxylation/hydrothioalkoxylation of nitrogen-tethered
alkenes and alcohols/thiols mediated by boron trifluoride etherate
leads to five-membered thiazolidine, six-membered 1,4-oxazines (morpholines)
and tetrahydro-2<i>H</i>-1,4-thiazines (thiomorpholines),
and seven-membered 1,4-oxazepanes in good yields