Abstract
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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3732-3735 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 14 |
| Issue number | 14 |
| DOIs | |
| State | Published - Jul 20 2012 |
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ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
Cite this
One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines. / Guggenheim, Kathryn G.; Toru, Hannah; Kurth, Mark J.
In: Organic Letters, Vol. 14, No. 14, 20.07.2012, p. 3732-3735.Research output: Contribution to journal › Article
}
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.
UR - http://www.scopus.com/inward/record.url?scp=84864124114&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84864124114&partnerID=8YFLogxK
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 -