Efficient synthesis of primary amides using 2-mercaptopyridone-1-oxide-based uronium salts

Authors
Bailen, MA Chinchilla, R Dodsworth, DJ Najera, C
Citation
Ma. Bailen et al., Efficient synthesis of primary amides using 2-mercaptopyridone-1-oxide-based uronium salts, TETRAHEDR L, 41(50), 2000, pp. 9809-9813
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
50
Year of publication
2000
Pages
9809 - 9813
Database
ISI
SICI code
0040-4039(200012)41:50<9809:ESOPAU>2.0.ZU;2-V
Abstract
S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium tetrafluoroborate (T OTT) and hexafluorophosphate (HOTT) are cheap and convenient reagents for t he rapid and high-yielding preparation of primary amides when reacted with carboxylic acids and ammonium chloride in the presence of diisopropylethyla mine. The reaction is chemoselective and undesired ammonolysis of other sen sitive functional groups is not observed. (C) 2000 Elsevier Science Ltd. Al l rights reserved.