Selective Iodine-Catalyzed Intermolecular Oxidative Amination of C(sp3)H Bonds with ortho-Carbonyl-Substituted Anilines to Give Quinazolines
Access to quinazolines: The selective amination of C(sp3)H bonds adjacent to nitrogen or oxygen atoms of N‐alkylamides, ethers, or alcohols with ortho‐carbonyl‐substituted anilines constitutes the first step in a tandem annulation that leads to quinazolines in good to excellent yields (see scheme;...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2012-08, Vol.51 (32), p.8077-8081 |
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| creator | Yan, Yizhe Zhang, Yonghui Feng, Chengtao Zha, Zhenggen Wang, Zhiyong |
| description | Access to quinazolines: The selective amination of C(sp3)H bonds adjacent to nitrogen or oxygen atoms of N‐alkylamides, ethers, or alcohols with ortho‐carbonyl‐substituted anilines constitutes the first step in a tandem annulation that leads to quinazolines in good to excellent yields (see scheme; NIS=N‐Iodosuccinimide, TBHP=tert‐butyl hydroperoxide). The selectivity of the amination of primary and secondary CH bonds is also noteworthy (left: >3:1, right: >99:1). |
| doi_str_mv | 10.1002/anie.201203880 |
| format | Article |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Alcohols Amination Aniline Aniline Compounds - chemistry Carbonyl compounds Catalysis Chemical reactions CH functionalization Ethers Hydrogen Bonding Iodine Iodine - chemistry Molecular Structure Organic chemistry Oxidation-Reduction oxidative coupling Oxygen atoms quinazolines Quinazolines - chemical synthesis Quinazolines - chemistry Selectivity |
| title | Selective Iodine-Catalyzed Intermolecular Oxidative Amination of C(sp3)H Bonds with ortho-Carbonyl-Substituted Anilines to Give Quinazolines |
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