Cyanuric Chloride Catalyzed Mild Protocol for Synthesis of Biologically Active Dihydro/Spiro Quinazolinones and Quinazolinone-glycoconjugates

We have developed an efficient cyanuric chloride (2,4,6-trichloro-1,3,5-triazine, TCT) catalyzed approach for the synthesis of 2,3-dihydroquinazolin-4­(1H)-one (3a–3x), 2-spiroquinazolinone (5, 7), and glycoconjugates of 2,3-dihydroquinazolin-4­(1H)-one (10a, 10b) derivatives. The reaction allows ra...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-01, Vol.77 (2), p.929-937
Main Authors: Sharma, Moni, Pandey, Shashi, Chauhan, Kuldeep, Sharma, Deepty, Kumar, Brijesh, Chauhan, Prem M. S
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Cyclization
Exact sciences and technology
Glycoconjugates - chemical synthesis
Glycoconjugates - chemistry
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Imines - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
ortho-Aminobenzoates
Preparations and properties
Quinazolinones - chemical synthesis
Quinazolinones - chemistry
Triazines - chemistry
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Summary:We have developed an efficient cyanuric chloride (2,4,6-trichloro-1,3,5-triazine, TCT) catalyzed approach for the synthesis of 2,3-dihydroquinazolin-4­(1H)-one (3a–3x), 2-spiroquinazolinone (5, 7), and glycoconjugates of 2,3-dihydroquinazolin-4­(1H)-one (10a, 10b) derivatives. The reaction allows rapid cyclization (8–20 min) with 10 mol % cyanuric chloride to give skeletal complexity in good to excellent yield. We believe that this novel procedure may open the door for the easy generation of new and bioactive quinazolinones.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo2020856