Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 17, Pages 3635-3643Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202000789
Keywords
2-Mercaptoimidazole; beta-Aminoacrylate; Isocyanides; alpha-Diazoacetates; Tandem Reaction
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Funding
- National Natural Science Foundation of China [21801050]
- Scientific Research Project of Guangzhou Municipal Colleges and Universities [201831816]
- Guangzhou University [2700050378]
- Natural Science Foundation of Shandong Province [ZR2018BB026]
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We have developed a palladium-catalyzed cross-coupling reaction of isocyanides with alpha-diazoacetates to form active ketenimines and following a 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed aza-Mannich type reaction with various 2-mercaptoimidazoles for the synthesis of 1,3-bis(beta-aminoacrylate)-substituted 2-mercaptoimidazole derivatives with structural diversity. In addition, the use of 1H-benzo[d]imidazol-2-ol as the reaction partner also allowed the formation of 1,3-bis(beta-aminoacrylate)-substituted 2-benzimidazolinone derivatives with moderate yields (34-52%). In the aza-Mannich reaction, the regioselectiveN-attack rather than S-attack or O-attack at the electrophilic central carbon of ketenimines was observed. This tandem sequence is efficient since two C=C and two C-N bonds are consecutively created in one-pot.
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