TY - JOUR
T1 - In Situ vinylpyrrole synthesis. Diels-alder reactions with maleimides to give tetrahydroindoles
AU - Noland, Wayland E.
AU - Lanzatella, Nicholas P.
AU - Sizova, Elena P.
AU - Venkatraman, Lakshmanan
AU - Afanasyev, Oleg V.
PY - 2009/5
Y1 - 2009/5
N2 - (Chemical Equation Presented) A series of 108 tetrahydroindoles has been prepared by a one-pot synthesis from 2-alkylpyrroles, cyclic ketones, maleimides, and an acid catalyst. A 5-vinylpyrrole is formed by an acid-catalyzed condensation of a 2-alkyl-substituted pyrrole with a ketone, which is subsequently trapped in situ by a maleimide in a predominantly endo-addition Diels-Alder reaction. Isomerization of the double bond into the pyrrole ring gives a tetrahydroindole with predominant cis-fusion of the cycloalkane ring.
AB - (Chemical Equation Presented) A series of 108 tetrahydroindoles has been prepared by a one-pot synthesis from 2-alkylpyrroles, cyclic ketones, maleimides, and an acid catalyst. A 5-vinylpyrrole is formed by an acid-catalyzed condensation of a 2-alkyl-substituted pyrrole with a ketone, which is subsequently trapped in situ by a maleimide in a predominantly endo-addition Diels-Alder reaction. Isomerization of the double bond into the pyrrole ring gives a tetrahydroindole with predominant cis-fusion of the cycloalkane ring.
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U2 - 10.1002/jhet.95
DO - 10.1002/jhet.95
M3 - Article
AN - SCOPUS:66349112905
SN - 0022-152X
VL - 46
SP - 503
EP - 534
JO - Journal of Heterocyclic Chemistry
JF - Journal of Heterocyclic Chemistry
IS - 3
ER -