En Route to 2-(Cyclobuten-1-yl)-3-(trifluoromethyl)-1H-indole.

  title={En Route to 2-(Cyclobuten-1-yl)-3-(trifluoromethyl)-1H-indole.},
  author={Martin Gazvoda and Marko Krivec and Zdenko {\vC}asar and Janez Ko{\vs}mrlj},
  journal={The Journal of organic chemistry},
  volume={83 4},
A six-step synthetic route from 4-chloro-2-methylaniline to 5-chloro-2-(cyclobut-1-en-1-yl)-3-(trifluoromethyl)-1H-indole (1) has been reported. Compound 1a is a key impurity of reverse transcriptase inhibitor efavirenz, an important anti-HIV/AIDS drug. Synthetic challenges, dead ends, and detours are discussed. 
4 Citations
An entry to 2-(cyclobut-1-en-1-yl)-1H-indoles through a cyclobutenylation/deprotection cascade.
Preliminary experimental and density functional theory calculations suggest that a Boc-group transfer is involved in the underlying mechanism of the synthesis of 2-(cyclobut-1-en- 1-yl)-1H-indoles. Expand
Oxidative ring-opening of isatins for the synthesis of 2-aminobenzamides and 2-aminobenzoates
Abstract An efficient and practical isatin-based oxidative domino protocol has been developed for the facile synthesis of 2-aminobenzamides and 2-aminobenzoates. The robust nature of this reactionExpand
Synthesis and properties of highly organosoluble aromatic polyimides containing N-(4-(di(1H-indole-3-yl)methyl)phenyl) moieties
A new diamine monomer containing indole unit, 3,5-diamino-N-(4-(di(1H-indol-3-yl)methyl)phenyl)benzamide, was successfully synthesized and applied in the preparation of a series of polyimides (PIs)Expand