TY - JOUR
T1 - One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines
AU - Guggenheim, Kathryn G.
AU - Toru, Hannah
AU - Kurth, Mark J.
PY - 2012/7/20
Y1 - 2012/7/20
N2 - An operationally simple, one-pot, two-step cascade method has been developed to afford quinazolino[1,2,3]triazolo[1,4]benzodiazepines. This unique, atom-economical transformation engages five reactive centers (amide, aniline, carbonyl, azide, and alkyne) and employs environmentally benign iodine as a catalyst. The method proceeds via sequential quinazolinone-forming condensation and intramolecular azide-alkyne 1,3-dipolar cycloaddition reactions. Substrate scope, multicomponent examples, and mechanistic insights are discussed.
AB - An operationally simple, one-pot, two-step cascade method has been developed to afford quinazolino[1,2,3]triazolo[1,4]benzodiazepines. This unique, atom-economical transformation engages five reactive centers (amide, aniline, carbonyl, azide, and alkyne) and employs environmentally benign iodine as a catalyst. The method proceeds via sequential quinazolinone-forming condensation and intramolecular azide-alkyne 1,3-dipolar cycloaddition reactions. Substrate scope, multicomponent examples, and mechanistic insights are discussed.
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U2 - 10.1021/ol301592z
DO - 10.1021/ol301592z
M3 - Article
C2 - 22746550
AN - SCOPUS:84864124114
VL - 14
SP - 3732
EP - 3735
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 14
ER -