One-pot synthesis and negative ion mass spectrometric investigation of a densely functionalized cinnoline

[Display omitted] 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-...

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Published inTetrahedron letters Vol. 56; no. 50; pp. 6980 - 6983
Main 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.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 16.12.2015
Elsevier
Subjects
Antimalarial
Chemistry
Chemistry, Organic
Cinnoline
Heme binding
Negative ion electrospray mass spectrometry
One-pot
Physical Sciences
Quinone-methide
Science & Technology
Antimalarial
Heme binding
Quinone-methide
LDVFTBNTUGZYBM-UHFFFAOYSA-N
UGNWTBMOAKPKBL-UHFFFAOYSA-N
Cinnoline
One-pot
CUONGYYJJVDODC-UHFFFAOYSA-N
Negative ion electrospray mass spectrometry
MECHANISM
DRUGS
ELECTRON OXIDATION
DERIVATIVES
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Summary:[Display omitted] 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.
Bibliography:researchfish
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.10.104