![6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-6-carboxylic acid structure](https://static.chemtradehub.com/structs/136/1369160-12-2-6524.webp "6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-6-carboxylic acid structure")
6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-6-carboxylic acid
CAS Number:
1369160-12-2
Molecular Formula:
C7H8N2O2
Synthesis of quinazolinones via radical cyclization of α-azidyl benzamides
Literature Information
Publication Date
2016-12-16
DOI
10.1039/C6QO00656F
Impact Factor
5.281
Authors
Tonghao Yang, Weixia Wang, Dian Wei, Tianqi Zhang, Bing Han, Wei Yu
View Original
Abstract
This paper reports a new radical-based method for the synthesis of quinazolinones from α-azidyl benzamides. Under the conditions of visible light irradiation with N-bromosuccinimide (NBS), α-azidyl benzamides were transformed into the corresponding iminyl radicals via regio-selective α-hydrogen abstraction and denitrogenation; the thus formed iminyl radicals then underwent cyclization to afford the quinazolinones. The scope of this method was examined by applying it to α-azidyl benzamides of different structural features. It was found that the key cyclization step is influenced by conformational effects as well as substituent effects. As the current approach can be implemented under mild tin-free conditions by using readily accessible precursors, it has practical applicability in the synthesis of quinazolinones.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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CAS Number:
1499167-72-4
Molecular Formula:
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2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraen-1-yloxy]-1,3-propanediol
CAS Number:
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Molecular Formula:
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