DMSO as a dual carbon synthon in one-pot tandem synthesis of N-alkylated quinazolinones from anthranilamides and acetophenones

Abstract

A new, efficient, metal-free, and DMSO intervened approach for the synthesis of N-alkylated quinazolinones from readily available 2-aminobenzamide and aryl methyl ketones in the presence of an oxidizing agent has...

Transition-metal-free C–S bond cleavage and transformation of organosulfur compounds

“…38 DMSO can be activated by K 2 S 2 O 8 to generate the sulfonium ion 12A , which is used as a source of the methenyl (CH) or methylene (CH 2 ) group. 39,40 In 2019, the Wu group developed a K 2 S 2 O 8 -initiated cycloaddition reaction of pyridinium salts 86 with DMSO in the presence of TFA and trimethylethylenediamine (TMEDA). In this process, the inexpensive K 2 S 2 O 8 compound activates DMSO to form the sulfonium ion 12A , which is converted into the final indolizine derivatives 87 (Scheme 16a).…”

“…39 Following this, the Tiwari group then performed a one-pot tandem reaction of anthranilamides 88 , aryl methyl ketones 75 and DMSO using K 2 S 2 O 8 for the synthesis of N -alkylated quinazolinones 89 (Scheme 16b). 40…”

DMSO arbitrated Oxidative Annulation Followed by Homologated N-Alkylation: Microwave-Assisted Efficient and Greener Approach to Access 3-(3-Oxo-3-arylpropyl) Quinazolinones

“…Furthermore, a very recent report demonstrated the synthesis of 3-(3-oxo-3-phenylpropyl)quinazolin-4(3 H )-one from readily available starting materials using a conventional synthetic method. 12 All the above-mentioned methods have few drawbacks of preparation of reaction intermediates, use of metal catalyst, and long reaction time. To overcome all the aforesaid inadequacies, there is a need to develop a new synthetic strategy.…”

Base-Promoted Annulated Aromatization of Aryl Acetylenes with Dimethyl Sulfoxide to Access Symmetrical/Unsymmetric m-Terphenyl

“…Herein, we disclosed a novel protocol for the selective and efficient synthesis of symmetrical and unsymmetrical m -terphenyls mediated by KOH and methanol (Scheme c). In this annulated aromatization reaction, two molecules of aryl acetylene contribute four carbons, and DMSO, as a dual carbon donor, provides two carbons to a new aromatic ring. This protocol can be tolerated for the electron-donating or disubstituted phenylacetylenes as well as the heterocyclic substituted acetylene derivatives and it is gram-scalable.…”