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

TETRAHEDRON LETTERS

卷:56

Article

Lambert, Daniel J.¹  Parikh, Nigam¹  Messham, Stephen J.¹  Edwards, Giles²  Hieu Van Truong¹  Dempster, Nicola M.¹  Drew, Michael G. B.³  Nahar, Lutfun¹  Sarker, Satyajit D.¹  Ismail, Fyaz M. D.¹ 

[1] Liverpool John Moores Univ, Sch Pharm & Biomol Sci, Med Chem & Nat Prod Res Grp, Liverpool L3 3AF, Merseyside, England

[2] Univ Manchester, Manchester Interdisciplinary Bioctr, Manchester M1 7DN, Lancs, England

[3] Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England

关键词: Cinnoline;    Antimalarial;    Quinone-methide;    One-pot;    Negative ion electrospray mass spectrometry;    Heme binding;   

DOI  :  10.1016/j.tetlet.2015.10.104

来源: Elsevier

【 摘 要 】

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. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

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