Chemoselectivity in coupling of azides with thioacids in solution-phase and solvent-free conditions

Synthetic Communications

Volumn 43, Issue 5, 2013, Pages 668-680

  Nagarajan, Sangaraiah ^a   Shanmugavelan, Poovan ^a   Sathishkumar, Murugan ^a   Priyadharshini, Namachivayam ^a   Sudakar, Padmanaban ^a   Ponnuswamy, Alagusundaram ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

Amide; chemoselectivity; glycerol bath; MW irradiation; solvent free; thioamide

Indexed keywords

AZIDE; CARBOXYLIC ACID DERIVATIVE; PHOSPHINE DERIVATIVE; THIOACID;

ARTICLE; METHODOLOGY; REACTION TIME; SOLUTION AND SOLUBILITY;

EID: 84869411359     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.606043     Document Type: Article

References (29)

1. 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.
2. Zenker, N.; Hubbard, L. S.; Wright, W. Inhibition of dopamine b-hydroxylase by goitrin, a natural antithyroid compound. J. Nat. Prod. 1988, 51, 862-865.
3. Jagodzinski, T. S. Thioamides as useful synthons in the synthesis of heterocycles. Chem. Rev. 2003, 103, 197-228.
4. 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.
5. (a) Petersson, M. J.; Marchal, C.; Loughlin, W. A.; Jenkins, I. D.; Healy, P. C.; Almesaker, A. Unexpected regiospecific reactivity of a substituted phthalic anhydride. Tetrahedron 2007, 63, 1395-1401; (Pubitemid 44969422)
6. (b) Maki, T.; Ishihara, K.; Yamamoto, H. New boron(III)-catalyzed amide and ester condensation reactions. Tetrahedron 2007, 63, 8645-8657; (Pubitemid 47068735)
7. (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. (Pubitemid 34185529)
8. (a) Staudinger, H.; Meyer, J. Uber neue organische phosphorverbindungen III: Phosphinmethylenderivate und phosphinimine. Helv. Chim. Acta 1919, 2, 635-646;
9. (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;
10. (c) Gololobov, Y. G.; Kasukhin, L. F. Recent advances in the Staudinger reaction. Tetrahedron 1992, 48, 1353-1406.
11. (a) Garca, J.; Urp, F.; Vilarrasa, J. New synthetic "tricks": Triphenylphosphine-mediated amide formation from carboxylic acids and azides. Tetrahedron Lett. 1984, 25, 4841-4844;
12. (b) Kovacs, L.; Osz, E.; Domokos, V.; Holzer, W.; Gyorgydesk, Z. An easy access to anomeric glycosyl amides and imines (Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides. Tetrahedron 2001, 57, 4609-4621; (Pubitemid 32441858)
13. (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; (Pubitemid 30666436)
14. (d) Urp, F.; Vilarrasa, J. New synthetic "tricks": Advantages of using triethylphosphine in some phosphorus-based reactions. Tetrahedron Lett. 1986, 27, 4623-4624;
15. (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;
16. (f) Bosch, I.; Gonzalez, A.; Urp, F.; Vilarrasa, J. On the reaction of acyl chlorides and carboxylic anhydrides with phosphazenes. J. Org. Chem. 1996, 61, 5638-5643. (Pubitemid 126532266)
17. (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; (Pubitemid 37141087)
18. (b) Charette, A. B.; Grenon, M. Mild method for the conversion of amides to thioamides. J. Org. Chem. 2003, 68, 5792-5794; (Pubitemid 36830550)
19. (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.
20. Kolakowski, R. V.; Shangguan, N.; Williams, L. J. Thioamides via thiatriazolines. Tetrahedron Lett. 2006, 47, 1163-1166. (Pubitemid 43084754)
21. 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. (Pubitemid 35222948)
22. 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.
23. 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.
24. 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.
25. 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. (Pubitemid 36789754)
26. Shi, M.; Cui, S.-C. Transamidation catalyzed by a recoverable and reusable polyDMAPbased hafnium chloride and montmorillonite KSF. Synth. Commun. 2005, 35, 2847-2858. (Pubitemid 41806182)
27. 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.
28. Yoo, W.-J.; Li, C.-J. Highly efficient oxidative amidation of aldehydes with amine hydrochloride salts. J. Am. Chem. Soc. 2006, 128, 13064-13065. (Pubitemid 44527671)
29. 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.