One-pot synthesis and negative ion mass spectrometric investigation of a densely functionalized cinnoline. Issue 50 (16th December 2015)

• Record Type: Journal Article
• Authors: Lambert, Daniel J.; Parikh, Nigam; Messham, Stephen J.; Edwards, Giles; van Truong, Hieu; Dempster, Nicola M.; Drew, Michael G.B.; Nahar, Lutfun; Sarker, Satyajit D.; Ismail, Fyaz M.D.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 50(2015)
• Page Start: 6980
• Page End: 6983
• Publication Date: 2015-12-16
• Subjects: UGNWTBMOAKPKBL-UHFFFAOYSA-N -- LDVFTBNTUGZYBM-UHFFFAOYSA-N -- CUONGYYJJVDODC-UHFFFAOYSA-N; Cinnoline -- Antimalarial -- Quinone-methide -- One-pot -- Negative ion electrospray mass spectrometry -- Heme binding; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.10.104
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Known, densely substituted 3-amino-5, 7, 8-trichloro-6-hydroxycinnoline-4-carbonitrile was synthesized using a one pot synthetic protocol under base-mediated conditions in a polar medium. Condensation of excess malononitrile with chloranil in ethanol at reflux gave quinone methide—2-(2, 4, 5-trichloro-3-hydroxy-6-oxocyclohexa-2, 4-dien-1-ylidene)malononitrile which was isolated as the triethylamine salt. This represents an atom efficient, simple, and effective procedure for the preparation of a highly substituted cinnolines that may serve as relay materials for antimalarial prototypes.