Plant-Based Bronsted Acidic Polyphenol Catalyzed Synthesis of 3'-Phenyl-1'H-Spiro[Cyclohexane-1,2'-Quinazolin]-4'(3'H)-Ones and 3'-Phenyl-1'H-Spiro[Cyclopentane-1,2'-Quinazolin]-4'(3'H)-One Derivatives

Abstract

An efficient, metal-free method for the synthesis of 3'-phenyl-1'H-spiro[cyclohexane-1,2'-quinazolin]-4'(3'H)-ones, 4-(tert-butyl)-3'-phenyl-1'H-spiro[cyclohexane-1,2'-quinazolin]-4'(3'H)-ones and 3'-phenyl-1'H-spiro[cyclopentane-1,2'-quinazolin]-4'(3'H)-one derivatives was developed using isatoic anhydride, cycloalkanone and different anilines through one-pot three-component cyclocondensation by utilizing tannic acid(TA)—a weakly acidic natural polyphenol, as a novel inexpensive greener catalyst. The reaction allows rapid cyclocondensation (10–30 min) at reflux condition with 5 mol% of tannic acid to give diversely functionalized spiroquinazolinones in good to excellent yield. This green protocol is of big interest due to employing simple, nontoxic and inexpensive tannic acid as a catalyst and environmentally benign aqueous ethanol as green solvent without the use of any harmful mineral acid and toxic transition metal catalyst.

Graphical Abstract

Keywords:

• tannic acid
• Spiroquinazolinones
• nitrogen heterocycles
• isatoic anhydride
• cyclic ketones
• multicomponent reaction

Correction Statement

This article has been corrected with minor changes. These changes do not impact the academic content of the article.

Acknowledgements

The authors are thankful to Faculty of Department of Chemistry, Arignar Anna Government Arts College, Cheyyar, India-604407 and Faculty of Department of Chemistry, Madras Christian College, Chennai, India-600059.

Disclosure statement

No potential conflict of interest was reported by the author(s).