One-pot synthesis and negative ion mass spectrometric investigation of a densely functionalized cinnoline, 3-amino-5,7,8-trichloro-6-hydroxycinnoline-4-carbonitrile

Lambert, DJ, Parikh, N, Messham, SJ, Edwards, G, Truong, HV, Dempster, NM, Drew, MGB, Nahar, L, Sarker, SD and Ismail, FMD (2015) One-pot synthesis and negative ion mass spectrometric investigation of a densely functionalized cinnoline, 3-amino-5,7,8-trichloro-6-hydroxycinnoline-4-carbonitrile. Tetrahedron Letters, 56 (50). pp. 6980-6983. ISSN 0040-4039

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Abstract

Known densely substituted 3-amino-5,7,8-trichloro-6-hydroxycinnoline-4-carbonitrile was synthesized using a new synthetic protocol involving chloranil and malonitrile via quinone methide formation. This one-pot synthesis occurs under base mediated conditions in a polar medium. The method involves condensation of excess malononitrile with chloranil in ethanol at reflux to 2-(2,4,5-trichloro-3-hydroxy-6-oxocyclohexa-2,4-dien-1-ylidene) malononitrile. This is an atom efficient, simple and effective procedure for the preparation of a highly substituted cinnoline that can serve as a relay to antimalarial prototypes.

Item Type:	Article
Subjects:	R Medicine > RM Therapeutics. Pharmacology R Medicine > RS Pharmacy and materia medica
Divisions:	Pharmacy and Biomolecular Sciences
Publisher:	Elsevier
Date of acceptance:	29 October 2015
Date of first compliant Open Access:	4 December 2015
Date Deposited:	04 Dec 2015 13:19
Last Modified:	02 Mar 2022 12:06
URI:	https://ljmu-9.eprints-hosting.org/id/eprint/2433

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