Synthesis of furan-linked iminomethyl 2-aminochromones via a base-promoted cascade reaction of 3-cyanochromones with β-ketodinitriles

Behnaz Farajpour; Fatima Khawari; Nafiseh Bakhshi Davoudi; Yazdanbakhsh Lotfi Nosood; Behrouz Notash; Salman Taheri; Fatemeh Moradkhani; Morteza Shiri; Ahmed Al-Harrasi; Faiq H. S. Hussain

doi:10.1039/D5OB01442E

Synthesis of furan-linked iminomethyl 2-aminochromones via a base-promoted cascade reaction of 3-cyanochromones with β-ketodinitriles

Behnaz Farajpour,

^a Fatima Khawari,^a Nafiseh Bakhshi Davoudi,^a Yazdanbakhsh Lotfi Nosood,

^b Behrouz Notash,

^c Salman Taheri,

^d Fatemeh Moradkhani,^e Morteza Shiri,

*^a Ahmed Al-Harrasi

*^b and Faiq H. S. Hussain

*^f

Author affiliations

* Corresponding authors

^a Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Vanak, Tehran 1993893973, Iran
E-mail: mshiri@alzahra.ac.ir

^b Natural and Medical Sciences Research Center, University of Nizwa, P. O. Box 33, Postal Code 616, Birkat Al Mauz, Nizwa, Sultanate of Oman

^c Department of Inorganic Chemistry, Shahid Beheshti University, Tehran 1983969411, Iran

^d Chemistry & Chemical Engineering Research Center of Iran, Tehran 1993893973, Iran

^e Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran P94V+8MF, Iran

^f Medical Analysis Department, Applied Science Faculty, Tishk International University, Erbil 44001 Kurdistan Region, Iraq

Abstract

A base-promoted reaction of 3-cyanochromones with β-ketodinitriles has been described to afford novel furan-linked iminomethyl 2-aminochromone derivatives in an efficient manner. This cascade reaction involves multiple transformations including the in situ generation of a 2-amino-furan intermediate/Michael-type addition/retro-Michael-type ring opening process/intramolecular O-cyclization/tautomerization under simple heating conditions. This facile process is distinguished by its operational simplicity, excellent atom efficiency, good functional group compatibility, easy purification, synthetically useful yields, and applicability for gram-scale synthesis.

Organic & Biomolecular Chemistry

Synthesis of furan-linked iminomethyl 2-aminochromones via a base-promoted cascade reaction of 3-cyanochromones with β-ketodinitriles

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Synthesis of furan-linked iminomethyl 2-aminochromones via a base-promoted cascade reaction of 3-cyanochromones with β-ketodinitriles

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