Abstract
A transition metal-free, one-pot protocol has been developed for the synthesis of 11H-indolo[3,2-c]isoquinolin-5-amines via the atom economical annulation of ethyl (2-cyano-phenyl)carbamates and 2-cyanobenzyl bromides. This method proceeds via sequential N-alkylation and base-promoted cyclization. Optimization data, substrate scope, mechanistic insights, and photoluminescence properties are discussed.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 5429-5433 |
| Number of pages | 5 |
| Journal | Tetrahedron Letters |
| Volume | 56 |
| Issue number | 40 |
| DOIs | |
| State | Published - Sep 30 2015 |
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Keywords
- Domino process
- Indolo[3,2-c]isoquinoline
- One-pot
- Photoluminescence
- Tandem cyclization
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-Alkylation/tandem cyclization. / Nguyen, Huy H.; Fettinger, James C.; Haddadin, Makhluf J.; Kurth, Mark J.
In: Tetrahedron Letters, Vol. 56, No. 40, 30.09.2015, p. 5429-5433.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-Alkylation/tandem cyclization
AU - Nguyen, Huy H.
AU - Fettinger, James C.
AU - Haddadin, Makhluf J.
AU - Kurth, Mark J.
PY - 2015/9/30
Y1 - 2015/9/30
N2 - A transition metal-free, one-pot protocol has been developed for the synthesis of 11H-indolo[3,2-c]isoquinolin-5-amines via the atom economical annulation of ethyl (2-cyano-phenyl)carbamates and 2-cyanobenzyl bromides. This method proceeds via sequential N-alkylation and base-promoted cyclization. Optimization data, substrate scope, mechanistic insights, and photoluminescence properties are discussed.
AB - A transition metal-free, one-pot protocol has been developed for the synthesis of 11H-indolo[3,2-c]isoquinolin-5-amines via the atom economical annulation of ethyl (2-cyano-phenyl)carbamates and 2-cyanobenzyl bromides. This method proceeds via sequential N-alkylation and base-promoted cyclization. Optimization data, substrate scope, mechanistic insights, and photoluminescence properties are discussed.
KW - Domino process
KW - Indolo[3,2-c]isoquinoline
KW - One-pot
KW - Photoluminescence
KW - Tandem cyclization
UR - http://www.scopus.com/inward/record.url?scp=84940706032&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84940706032&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2015.08.006
DO - 10.1016/j.tetlet.2015.08.006
M3 - Article
VL - 56
SP - 5429
EP - 5433
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 40
ER -