Potent triazine-based dehydrocondensing reagents substituted by an amido group

• Munetaka Kunishima,
• Daiki Kato,
• Nobu Kimura,
• Masanori Kitamura,
• Kohei Yamada and
• Kazuhito Hioki

Beilstein J. Org. Chem. 2016, 12, 1897–1903, doi:10.3762/bjoc.12.179

• reactions; amido substituents; dehydrocondensing reactions; Fischer-type esterification; triazines; Introduction We previously reported that dehydrocondensing reactions between carboxylic acids 1 and amines 2 to give amides 3 efficiently proceed in water or alcohols in the presence of the dehydrocondensing

• -forming reactions. Time courses of the basic Fischer-type esterification. Dehydrocondensing reactions using DMT-MM or DMT-Am, and a catalytic amide-forming reaction. Synthesis of amido-substituted chlorotriazines. Amide-forming reactions using chlorotriazines (I–VI) or triazinylammonium salts (VII–X

• of 1b was suitable to investigate the reaction rates for X and DMT-MM. Although the final yields of the amide were almost the same for both triazines, the rate of the reaction with X was faster than that with DMT-MM, particularly in THF. Similarly, time courses of the basic Fischer-type

Directed aromatic functionalization in natural-product synthesis: Fredericamycin A, nothapodytine B, and topopyrones B and D

• Charles Dylan Turner and
• Marco A. Ciufolini

Beilstein J. Org. Chem. 2011, 7, 1475–1485, doi:10.3762/bjoc.7.171

• converted into an acetate ester (Fischer-type esterification). Compound 15, a form of 4 suitable for the conduction of subsequent operations, was secured by deacetylation of 14 and Swern oxidation. Fragment 5 was best produced in the guise of compound 20, the construction of which also relied upon DAF