Department of Chemistry, Institute of Chemical Technology , Mumbai 400019, India.
J Org Chem. 2017 Jun 2;82(11):5769-5781. doi: 10.1021/acs.joc.7b00570. Epub 2017 May 12.
This work reports tert-butyl nitrite (TBN) as a multitask reagent for (1) the controlled synthesis of N-nitrosoamide from N-alkyl amides, (2) hydrolysis of N-methoxyamides to carboxylic acids, (3) metal- and oxidant-free benzocoumarin synthesis from ortho-aryl-N-methoxyamides via N-H, C-N, and C-H bond activation, and (4) isocoumarin synthesis using Ru(II)/PEG as a recyclable catalytic system via ortho-C-H activation and TBN as an oxygen source. The sequential functional group interconversion of amide to acid has also been examined using IR spectroscopic analysis. Additionally, this methodology is highly advantageous due to short reaction time, gram scale synthesis, and broad substrate scope.
这项工作报道了叔丁基亚硝酸盐（TBN）作为一种多任务试剂，可用于（1）通过 N-烷基酰胺控制合成 N-亚硝基酰胺，（2）通过 N-甲氧基酰胺的水解生成羧酸，（3）通过 N-H、C-N 和 C-H 键的活化，从邻芳基-N-甲氧基酰胺合成无金属和氧化剂的苯并[g]色满，以及（4）使用 Ru(II)/PEG 通过邻-C-H 活化和 TBN 作为氧源作为可回收催化体系合成异香豆素。酰胺到酸的连续官能团转化也通过红外光谱分析进行了检查。此外，由于反应时间短、克级合成和广泛的底物范围，该方法具有很高的优势。
