Copper‐Catalyzed Oxidative C−C Cleavage of Carbohydrates: An Efficient Access to Quinazolinone Scaffolds | Zendy

Philips Abigail | Zendy; Raja Dineshkumar | Zendy; Arumugam Ajithkumar | Zendy; Lin WeiYu | Zendy; Chandru Senadi Gopal | Zendy

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Copper‐Catalyzed Oxidative C−C Cleavage of Carbohydrates: An Efficient Access to Quinazolinone Scaffolds

Author(s) -

Philips Abigail,

Raja Dineshkumar,

Arumugam Ajithkumar,

Lin WeiYu,

Chandru Senadi Gopal

Publication year - 2021

Publication title -

asian journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.846

H-Index - 44

eISSN - 2193-5815

pISSN - 2193-5807

DOI - 10.1002/ajoc.202100317

Subject(s) - synthon , chemistry , quinazolinone , catalysis , oxidative phosphorylation , oxidative coupling of methane , combinatorial chemistry , organic chemistry , biochemistry

A copper‐catalyzed oxidative coupling strategy has been developed for the synthesis of 4(3 H )‐quinazolinones and benzoimidazoquinazoline using glucose as renewable C 1 synthon. Isotope labelling studies using 13 C 6 D ‐glucose and DMSO‐ d 6 confirmed the role of D ‐glucose as C 1 source. The significant features of this method include (i) utilization of 0.25 to 0.5 equiv., of D ‐glucose as a multi‐C 1 synthon; (ii) biomass‐derived platform chemical as carbon synthon; (iii) atom‐economical and benign conditions and; (iv) synthesis of naturally occurring alkaloid and precursor.

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