Chemoselectivity in Coupling of Azides with Thioacids in Solution-Phase and Solvent-Free Conditions

REFERENCES

• Tinnis , F. ; Adolfsson , H. Asymmetric transfer hydrogenation of ketones catalyzed by rhodium complexes containing amino acid triazole ligand . Org. Biomol. Chem. 2010 , 8 , 4536 – 4539 .
   PubMed Web of Science ®Google Scholar
• Zenker , N. ; Hubbard , L. S. ; Wright , W. Inhibition of dopamine β-hydroxylase by goitrin, a natural antithyroid compound . J. Nat. Prod. 1988 , 51 , 862 – 865 .
   PubMed Web of Science ®Google Scholar
• Jagodziński , T. S. Thioamides as useful synthons in the synthesis of heterocycles . Chem. Rev. 2003 , 103 , 197 – 228 .
   PubMed Web of Science ®Google Scholar
• Wipf , P. ; Miller , C. P. ; Venkatraman , S. ; Fritch , P. C. Thiolysis of oxazolines: A new, selective method for the direct conversion of peptide oxazolines into thiazolines . Tetrahedron Lett. 1995 , 36 , 6395 – 6398 .
   Web of Science ®Google Scholar
• (a) Petersson , M. J. ; Marchal , C. ; Loughlin , W. A. ; Jenkins , I. D. ; Healy , P. C. ; Almesáker , A. Unexpected regiospecific reactivity of a substituted phthalic anhydride . Tetrahedron 2007 , 63 , 1395 – 1401 ; (b) Maki , T. ; Ishihara , K. ; Yamamoto , H. New boron(III)-catalyzed amide and ester condensation reactions . Tetrahedron 2007 , 63 , 8645 – 8657 ; (c) Perreux , L. ; Loupy , A. ; Volatron , F. Solvent-free preparation of amides from acids and primary amines under microwave irradiation . Tetrahedron 2002 , 58 , 2155 – 2162 .
   Web of Science ®Google Scholar
• (a) Staudinger , H. ; Meyer , J. Über neue organische phosphorverbindungen III: Phosphinmethylenderivate und phosphinimine . Helv. Chim. Acta 1919 , 2 , 635 – 646 ; (b) Gololobov , Y. G. ; Zhmurova , I. N. ; Kasukhin , L. F. Frequency and type of confrontation over time within the first therapy interview . Tetrahedron 1981 , 37 , 437 – 472 ; (c) Gololobov , Y. G. ; Kasukhin , L. F. Recent advances in the Staudinger reaction . Tetrahedron 1992 , 48 , 1353 – 1406 .
   Web of Science ®Google Scholar
• (a) García , J. ; Urpí , F. ; Vilarrasa , J. New synthetic “tricks”: Triphenylphosphine-mediated amide formation from carboxylic acids and azides . Tetrahedron Lett. 1984 , 25 , 4841 – 4844 ; (b) Kovács , L. ; Osz , E. ; Domokos , V. ; Holzer , W. ; Györgydesk , Z. An easy access to anomeric glycosyl amides and imines (Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides . Tetrahedron 2001 , 57 , 4609 – 4621 ; (c) Malkinson , J. P. ; Falconer , R. A.; Toth I. Synthesis of C-terminal glycopeptides from resin-bound glycosyl azides via a modified Staudinger reaction . J. Org. Chem. 2000 , 65 , 5249 – 5252 ; (d) Urpí , F. ; Vilarrasa , J. New synthetic “tricks”: Advantages of using triethylphosphine in some phosphorus-based reactions . Tetrahedron Lett. 1986 , 27 , 4623 – 4624 ; (e) Shalev , D. E. ; Chiacchiera , S. M. ; Radkowsky , A. E. ; Kosower , E. M. Sequence of reactant combination alters the course of the Staudinger reaction of azides with acyl derivatives. Bimanes, 30 . J. Org. Chem. 1996 , 61 , 1689 – 1701 ; (f) Bosch , I. ; González , A. ; Urpí , F. ; Vilarrasa , J. On the reaction of acyl chlorides and carboxylic anhydrides with phosphazenes . J. Org. Chem. 1996 , 61 , 5638 – 5643 .
   Google Scholar
• (a) Coats , S. J. ; Link , J. S. ; Hlasta , D. J. Alternative solvents for elevated-temperature solid-phase parallel synthesis: Application to thionation of amides . Org. Lett. 2003 , 5 , 721 – 724 ; (b) Charette , A. B. ; Grenon , M. Mild method for the conversion of amides to thioamides . J. Org. Chem. 2003 , 68 , 5792 – 5794 ; (c) Ilankumaran , P. ; Ramesha , A. R. ; Chandrasekaran , S. A facile conversion of amides and lactams to thioamides and thiolactams using tetrathiomolybdate . Tetrahedron Lett. 1995 , 36 , 8311 – 8314 and references quoted therein .
   PubMed Web of Science ®Google Scholar
• Kolakowski , R. V. ; Shangguan , N. ; Williams , L. J. Thioamides via thiatriazolines . Tetrahedron Lett. 2006 , 47 , 1163 – 1166 .
   Web of Science ®Google Scholar
• Park , S.-D. ; Oh , J.-H. ; Lim , D. A new type of amide formation from thiocarboxylic acid and alkyl azide . Tetrahedron Lett. 2002 , 43 , 6309 – 6311
   Web of Science ®Google Scholar
• Sathishkumar , M. ; Shanmugavelan , P. ; Nagarajan , S. ; Maheswari , M. ; Dinesh , M. ; Ponnuswamy , A. Solvent-free protocol for amide bond formation via trapping of nascent phosphazenes with carboxylic acids. Tetrahedron Lett. 2011, 52, 2830–2833.
   Web of Science ®Google Scholar
• Sathishkumar , M. ; Nagarajan , S. ; Shanmugavelan , P. ; Dinesh , M. ; Ponnuswamy , A. Microwave-assisted clean synthesis of amides via aza-Witting reaction under solvent-free conditions . J. Braz. Chem. Soc. 2011 , 22 , 2065 – 2069 .
   Web of Science ®Google Scholar
• Rosen , T. ; Lico , I. M. ; Chu , D. T. W. A convenient and highly chemoselective method for the reductive acetylation of azides . J. Org. Chem. 1988 , 53 , 1580 – 1582 .
   Web of Science ®Google Scholar
• Shangguan , N. ; Katukojvala , S. ; Greenberg , R. ; Williams , L. J. The reaction of thio acids with azides: A new mechanism and new synthetic applications . J. Am. Chem. Soc. 2003 , 125 , 7754 – 7755 .
   PubMed Web of Science ®Google Scholar
• Shi , M. ; Cui , S.-C. Transamidation catalyzed by a recoverable and reusable polyDMAP-based hafnium chloride and montmorillonite KSF . Synth. Commun. 2005 , 35 , 2847 – 2858 .
   Web of Science ®Google Scholar
• Pathak , U. ; Pandey , L. K. ; Mathur , S. ; Suryanarayana , M. V. S. Ketoximes to N-substituted thioamides via PSCl3-mediated Beckmann rearrangement . Chem. Commun. 2009 , 5409 – 5411 .
   Web of Science ®Google Scholar
• Yoo , W.-J. ; Li , C.-J. Highly efficient oxidative amidation of aldehydes with amine hydrochloride salts . J. Am. Chem. Soc. 2006 , 128 , 13064 – 13065 .
   Web of Science ®Google Scholar
• Yde , B. ; Yousif , N. M. ; Pedersen , U. ; Thomsen , I. ; Lawesson , S.-O. Studies on organophosphorus compounds, XLVII: Preparation of thiated synthons of amides, lactams, and imides by use of some new p,s-containing reagents . Tetrahedron 1984 , 40 , 2047 – 2052 .
   Web of Science ®Google Scholar