TY - JOUR
T1 - Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols
AU - Seregin, Ilya V.
AU - Schammel, Alex W.
AU - Gevorgyan, Vladimir
N1 - Funding Information:
The support of the National Institutes of Health (Grant GM-64444) and National Science Foundation (Grant CHE 0354613) is gratefully acknowledged.
PY - 2008/7/14
Y1 - 2008/7/14
N2 - Two complementary protocols for assembly of multisubstituted N-fused heterocycles have been developed. It was demonstrated that 1,3-disubstituted N-fused heterocycles, including indolizines, pyrroloquinoxalines, and pyrrolothiazoles can easily be synthesized via an exceptionally mild and efficient method involving a novel silver-catalyzed cycloizomerization of propargyl-containing heterocycles. Alternatively, 1,2-disubstituted heterocycles can be accessed through the novel cascade transformation involving an alkyne-vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, stannyl, or germyl groups. This mild and simple method allows for selective and highly efficient synthesis of indolizines, pyrroloisoquinolines, pyrroloquinoxalines, pyrrolopyrazines, and pyrrolothiazoles.
AB - Two complementary protocols for assembly of multisubstituted N-fused heterocycles have been developed. It was demonstrated that 1,3-disubstituted N-fused heterocycles, including indolizines, pyrroloquinoxalines, and pyrrolothiazoles can easily be synthesized via an exceptionally mild and efficient method involving a novel silver-catalyzed cycloizomerization of propargyl-containing heterocycles. Alternatively, 1,2-disubstituted heterocycles can be accessed through the novel cascade transformation involving an alkyne-vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, stannyl, or germyl groups. This mild and simple method allows for selective and highly efficient synthesis of indolizines, pyrroloisoquinolines, pyrroloquinoxalines, pyrrolopyrazines, and pyrrolothiazoles.
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U2 - 10.1016/j.tet.2008.04.023
DO - 10.1016/j.tet.2008.04.023
M3 - Article
C2 - 19606205
AN - SCOPUS:44949130561
SN - 0040-4020
VL - 64
SP - 6876
EP - 6883
JO - Tetrahedron
JF - Tetrahedron
IS - 29
ER -