tert-Butyl Nitrite-Mediated Synthesis of N‑Nitrosoamides, Carboxylic Acids, Benzocoumarins, and Isocoumarins from Amides

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 b...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 82; no. 11; pp. 5769 - 5781
Main Authors Yedage, Subhash L, Bhanage, Bhalchandra M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.06.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
RECYCLABLE CATALYTIC-SYSTEM
TRANSAMIDATION REACTIONS
2-ARYLBENZOIC ACIDS
SOLVENT-FREE CONDITIONS
ONE-POT SYNTHESIS
3-SUBSTITUTED ISOCOUMARINS
EFFICIENT SYNTHESIS
ACTIVATION/ALKYNE ANNULATION
H BOND FUNCTIONALIZATION
BENZOIC-ACIDS
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00570