Abstract
An efficient method for the synthesis of polysubstituted cyclopentene and cyclopenta[b]carbazole derivatives through the iodine-promoted electrocyclization of substituted indoles and 4-arylidene-3,6-diarylhex-2-en-5-ynal derivatives is reported. Polysubstituted cyclopentene derivatives were produced through 4π electrocyclization reactions with indole, 7-methylindole, and 5-bromoindole as coupling partners, whereas cyclopenta[b]carbazole derivatives were produced via 6π electrocyclization in the case of methoxy (-OMe)-substituted indoles. The methods reported herein diastereo- and regioselectively proceed under straightforward and mild conditions.
| Original language | English |
|---|---|
| Pages (from-to) | 3036-3044 |
| Number of pages | 9 |
| Journal | Journal of Organic Chemistry |
| Volume | 84 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 2019 Mar 15 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Synthesis of Polysubstituted Cyclopentene and Cyclopenta[ b]carbazole Analogues from Unsymmetrical 4-Arylidene-3,6-diarylhex-2-en-5-ynal and Indole Derivatives via an Iodine Mediated Electrocyclization Reaction. / Bandi, Vijayalakshmi; Kavala, Veerababurao; Konala, Ashok; Hsu, Che Hao; Villuri, Bharath Kumar; Reddy, Sabbasani Rajasekhara; Lin, Lichun; Kuo, Chun Wei; Yao, Ching Fa.
In: Journal of Organic Chemistry, Vol. 84, No. 6, 15.03.2019, p. 3036-3044.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Synthesis of Polysubstituted Cyclopentene and Cyclopenta[ b]carbazole Analogues from Unsymmetrical 4-Arylidene-3,6-diarylhex-2-en-5-ynal and Indole Derivatives via an Iodine Mediated Electrocyclization Reaction
AU - Bandi, Vijayalakshmi
AU - Kavala, Veerababurao
AU - Konala, Ashok
AU - Hsu, Che Hao
AU - Villuri, Bharath Kumar
AU - Reddy, Sabbasani Rajasekhara
AU - Lin, Lichun
AU - Kuo, Chun Wei
AU - Yao, Ching Fa
PY - 2019/3/15
Y1 - 2019/3/15
N2 - An efficient method for the synthesis of polysubstituted cyclopentene and cyclopenta[b]carbazole derivatives through the iodine-promoted electrocyclization of substituted indoles and 4-arylidene-3,6-diarylhex-2-en-5-ynal derivatives is reported. Polysubstituted cyclopentene derivatives were produced through 4π electrocyclization reactions with indole, 7-methylindole, and 5-bromoindole as coupling partners, whereas cyclopenta[b]carbazole derivatives were produced via 6π electrocyclization in the case of methoxy (-OMe)-substituted indoles. The methods reported herein diastereo- and regioselectively proceed under straightforward and mild conditions.
AB - An efficient method for the synthesis of polysubstituted cyclopentene and cyclopenta[b]carbazole derivatives through the iodine-promoted electrocyclization of substituted indoles and 4-arylidene-3,6-diarylhex-2-en-5-ynal derivatives is reported. Polysubstituted cyclopentene derivatives were produced through 4π electrocyclization reactions with indole, 7-methylindole, and 5-bromoindole as coupling partners, whereas cyclopenta[b]carbazole derivatives were produced via 6π electrocyclization in the case of methoxy (-OMe)-substituted indoles. The methods reported herein diastereo- and regioselectively proceed under straightforward and mild conditions.
UR - http://www.scopus.com/inward/record.url?scp=85055640907&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85055640907&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.8b02168
DO - 10.1021/acs.joc.8b02168
M3 - Article
C2 - 30359006
AN - SCOPUS:85055640907
VL - 84
SP - 3036
EP - 3044
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 6
ER -