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
N1 - Funding Information:
Financial support by the Ministry of Science and Technology of the Republic of China (MOST 103-2113-M −003-008-MY3), National Taiwan Normal University (103-07-C), and Instrumentation Centre at National Taiwan Normal University is gratefully acknowledged. The authors are grateful to Ms. Hsiu- Ni Huang, Ms. Chiu-Hui He, and Mr. Ting-Shen Kuo for providing HRMS, NMR spectral, and crystallographic data, respectively.
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 -