Rapid Access to 1,2,3,4-Tetrasubstituted Benzenes and 3-Alkenyl-1,2-dihydropyridines
ACS OMEGA, vol.11, no.19, pp.29061-29084, 2026 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 11 Issue: 19
- Publication Date: 2026
- Doi Number: 10.1021/acsomega.6c02327
- Journal Name: ACS OMEGA
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Directory of Open Access Journals
- Page Numbers: pp.29061-29084
- Middle East Technical University Affiliated: Yes
Abstract
Herein, we report unprecedented protocols for the synthesis of 1,2,3,4-tetrasubstituted benzenes and 3-alkenyl-1,2-dihydropyridines from readily available N-methyl-N-propargyl beta-enaminones. When subjected to the reaction with dialkyl acetylenedicarboxylates in refluxing toluene under gold catalysis, N-methyl-N-propargyl beta-enaminones afforded 1,2,3,4-tetrasubstituted benzenes. On the other hand, the reaction of N-methyl-N-propargyl beta-enaminones with dialkyl acetylenedicarboxylates in refluxing acetonitrile under copper catalysis formed 3-alkenyl-1,2-dihydropyridines as the major product, accompanied by 1,2,3,4-tetrasubstituted benzenes as the minor product. An internal alkyne-tethered N-methyl-N-propargyl beta-enaminone yielded a pentasubstituted benzene derivative under both gold and copper catalysis. The skeletal diversity of the synthesized 1,2,3,4-tetrasubstituted benzenes and 3-alkenyl-1,2-dihydropyridines may be of use in medicinal and pharmaceutical chemistry as new and novel molecular entities and structural leads.