PMID: 28497830DOI: 10.1039/c7ob00715aMay 13, 2017Paper
FeCl3 catalysed 7-membered ring formation in a single pot: a new route to indole-fused oxepines/azepines and their cytotoxic activity
Organic & Biomolecular Chemistry
K Shiva KumarRama Krishna Kancha
Abstract
Various oxepine and azepine fused N-heterocyclic derivatives were synthesized using a new and one-pot reaction of 2,3-dichloro quinoxaline/pyrazine with 2-(1H-indol-2-yl)phenol/aniline in the presence of 25 mol% FeCl3. The reaction proceeded via C-C bond followed by C-X (X = O or N) bond formation to construct the central 7-membered ring, affording the desired products in good yields. The structure assignment was confirmed by the single crystal X-ray analysis of a synthesized oxepine fused N-heterocycle derivative. Most of the synthesized compounds were found to be promising when tested for their anti-proliferative properties against cervical and breast cancer cell lines.
References
Jan 1, 1999·Bioorganic & Medicinal Chemistry Letters·K ZimmermannP Waldmeier
Oct 13, 2000·British Journal of Pharmacology·Y SagotA C Kato
May 25, 2002·The Journal of Organic Chemistry·Mark LautensSandrine Piguel
May 23, 2003·Molecular Pharmacology·Hanlin GaoRobert M Snapka
Dec 9, 2004·Chemical Reviews·Carsten BolmLorenzo Zani
Mar 12, 2005·CA: a Cancer Journal for Clinicians·D Max ParkinPaola Pisani
Sep 10, 2005·The Journal of Organic Chemistry·Seiji YamaguchiYoshiro Hirai
Oct 21, 2005·Organic Letters·Mónica CarrilEsther Domínguez
Mar 28, 2006·Journal of Natural Products·George R PettitGordon M Cragg
Apr 22, 2008·Journal of Natural Medicines·Hideji ItokawaKuo-Hsiung Lee
May 24, 2008·Chemical Society Reviews·Arkaitz CorreaCarsten Bolm
Jul 8, 2008·Chemistry : a European Journal·Peter Spiteller
Dec 6, 2008·Organic Letters·Kazuhiro HiguchiTomomi Kawasaki
Apr 7, 2009·Bioorganic & Medicinal Chemistry Letters·Suh-Hee LeeWon-Jea Cho
Jun 27, 2009·Chemical Communications : Chem Comm·Jacob AndersenKristian Strømgaard
Jul 25, 2009·Bioorganic & Medicinal Chemistry Letters·Santhosh F NeelamkavilGiuseppe Terracina
Apr 14, 2010·Journal of Natural Products·Yulin RenA Douglas Kinghorn
Apr 16, 2010·The Journal of Organic Chemistry·Nitin T PatilBalasubramanian Sridhar
May 8, 2010·Angewandte Chemie·Alejandro Varela-FernándezCarlos Saá
Aug 12, 2010·The Journal of Organic Chemistry·Hai-Ming GuoGui-Rong Qu
Aug 31, 2010·Bioorganic & Medicinal Chemistry·Liang SunIwao Ojima
Jan 27, 2011·Chemistry : a European Journal·Ella Min Ling SzePhilip Wai Hong Chan
Jun 24, 2011·Bioorganic & Medicinal Chemistry Letters·Jianwei XieYiqian Wan
Jul 13, 2011·The Journal of Organic Chemistry·Xufen Yu, Xiyan Lu
Jul 26, 2011·Planta medica·Wisinee ChanmahasathienPornngarm Limtrakul
Feb 10, 2012·Bioorganic & Medicinal Chemistry·K Shiva KumarManojit Pal
Sep 6, 2012·Organic Letters·Jun Liu, Yuanhong Liu
Dec 12, 2012·Chemical Communications : Chem Comm·Peng SangYuhong Zhang
Jan 25, 2013·Organic Letters·Xiu-Hua XuNorio Shibata
Aug 29, 2014·Organic Letters·Peng ZhangBin-Gui Wang
Transition-metal-free synthesis of indole-fused dibenzo[b,f][1,4]oxazepines via Smiles rearrangement
Nov 16, 2016·Organic & Biomolecular Chemistry·Fangdong HuChen Ma
Dec 3, 2016·Organic & Biomolecular Chemistry·K Shiva KumarManojit Pal
❮ Previous
Next ❯
Citations
Oct 31, 2019·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Suman ChirraVenkatathri Narayanan
Apr 4, 2020·Organic & Biomolecular Chemistry·Siddi Ramulu MeesaK Shiva Kumar
May 19, 2021·The Journal of Organic Chemistry·Zong-Wang QiuXiang-Zhi Zhang
Sep 22, 2018·Organic Letters·K Shiva KumarPraveen Kumar Naikawadi
❮ Previous
Next ❯
Related Concepts
Related Feeds
Related Papers
Organic Letters
Bhimapaka China RajuBalasubramanian Sridhar
Bioorganic & Medicinal Chemistry Letters
Naveen MulakayalaManojit Pal
Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Sobhi M GomhaYahia N Mabkhot
Bioorganic & Medicinal Chemistry
K Shiva KumarManojit Pal
Organic & Biomolecular Chemistry
Surjeet SinghRamendra Pratap