A new approach to construct a fused 2-ylidene chromene ring: highly regioselective synthesis of novel chromeno quinoxalines

Organic & Biomolecular Chemistry
K Shiva KumarManojit Pal

Abstract

Regioselective construction of a fused 2-ylidene chromene ring was achieved for the first time by using AlCl(3)-induced C-C bond formation followed by Pd/C-Cu mediate coupling-cyclization strategy. A number of chromeno[4,3-b]quinoxaline derivatives were prepared by using this strategy. Single crystal X-ray diffraction study of a representative compound e.g. 6-(2,2-dimethylpropylidene)-4-methyl-6H-chromeno[4,3-b]quinoxalin-3-ol confirmed the presence of an exocyclic C-C double bond with Z-geometry. The crystal structure analysis and hydrogen bonding patterns of the same compound along with its structure elaboration via propargylation followed by Sonogashira coupling of the resulting terminal alkyne is presented. A probable mechanism for the formation of 2-ylidene chromene ring is discussed. Some of the compounds synthesized showed anticancer properties when tested in vitro.

References

Jan 1, 1992·Acta Oncologica·S Lundgren
Sep 10, 2004·Journal of the American Chemical Society·Tuanli YaoRichard C Larock
Mar 12, 2005·The Journal of Organic Chemistry·Manojit PalSrinivas Padakanti
Mar 12, 2005·CA: a Cancer Journal for Clinicians·D Max ParkinPaola Pisani
Feb 28, 2007·Chemical Communications : Chem Comm·Nalivela Kumara SwamyManojit Pal
Aug 21, 2007·Journal of Medicinal Chemistry·Andrew R HudsonLin Zhi

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Citations

Jun 25, 2013·Chemical Reviews·Rafael Chinchilla, Carmen Nájera
Aug 8, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Dahye LeeJae Hong Seo
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ana BornadiegoCarlos F Marcos

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