Iron-Catalyzed One-pot Synthesis of Indole-tethered Tetrasubstituted Pyrroles and Their Transformations to Indolizino[8,7-b]indole Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Xue Xiao ◽  
Xiao-Hui Chen ◽  
Xian-Xun Wang ◽  
Wan-Zhen Li ◽  
Hai-Lei Cui

We have developed an efficient iron-catalyzed one-pot reaction of tryptamines, ynones and nitroolefins affording indole-tethered tetrasubstituted pyrroles in acceptable to good yields. Other aromatic and aliphatic amines can also be utilized in this process delivering corresponding highly functionalized tetrasubstituted pyrroles. Indolizino[8,7-b]indole derivatives could be obtained through TFA, TfOH or Fe(OTf)3-mediated cyclizations via dearomatization of indole. Unexpected dibrominated products, 7,9-dibromo-6,11-dihydro-5H-indolizino[8,7-b]indoles, were formed when PTAP was employed as electrophilic cyclization promoter.

2017 ◽  
Vol 53 (34) ◽  
pp. 4718-4721 ◽  
Author(s):  
Xi Mao ◽  
Tao Tong ◽  
Senbao Fan ◽  
Liting Fang ◽  
Jingyi Wu ◽  
...  

A novel and expedient one-pot synthesis of thiazino[2,3,4-hi]indole derivatives was developed through a tandem oxidative coupling/heteroannulation process.


Molecules ◽  
2007 ◽  
Vol 12 (7) ◽  
pp. 1438-1446 ◽  
Author(s):  
Hossien Oskooie ◽  
Majid Heravi ◽  
Farahnaz Behbahani

ChemInform ◽  
2007 ◽  
Vol 38 (15) ◽  
Author(s):  
Jingliang Jiao ◽  
Yang Zhang ◽  
Robert A. II Flowers

2014 ◽  
Vol 20 (44) ◽  
pp. 14344-14350 ◽  
Author(s):  
Srinivas Samala ◽  
Pragyan Pallavi ◽  
Ravi Kumar ◽  
Rajesh K Arigela ◽  
Gajendra Singh ◽  
...  

ChemInform ◽  
2016 ◽  
Vol 47 (3) ◽  
Author(s):  
Jagatheeswaran Kothandapani ◽  
Asaithampi Ganesan ◽  
Subramaniapillai Selva Ganesan

Synlett ◽  
2006 ◽  
Vol 2006 (19) ◽  
pp. 3355-3357 ◽  
Author(s):  
Robert Flowers II ◽  
Jingliang Jiao ◽  
Yang Zhang

2014 ◽  
Vol 24 (18) ◽  
pp. 4501-4503 ◽  
Author(s):  
B.V. Subba Reddy ◽  
A. Venkata Ganesh ◽  
M. Vani ◽  
T. Ramalinga Murthy ◽  
Shasi V Kalivendi ◽  
...  

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