A Single-Reagent-Driven Multistep One-Pot Preparation of Thiazolines and 1,3-Thiazines from Aldoximes, Nitriles, and Carboxylic­ Acids

Abstract

N-(ω-Bromoalkyl)dichlorothiophosphoramidates have been designed as a new class of reagent for the single-reagent-driven multistep preparation of 2-substituted thiazolines and 1,3-thiazines from ald­oximes, nitriles, or carboxylic acids. A wide range of substrates both aromatic as well as aliphatic were investigated and found suitable for the developed protocol.

Key words

heterocycles - sulfur - tandem reaction - green chemistry - cyclization

• References

• 1a Eicher T, Hauptman S, Speicher A In The Chemistry of Heterocycles: Structure, Reactions, Syntheses and Applications . Wiley-VCH; New York: 2003
• 1b Katrizky AR, Pozhashii AF. Handbook of Heterocyclic Chemistry . Elsevier Science; Amsterdam: 2000
• 1c Gilman AG, Goodman LS. The Pharmacological Basis of Therapeutics . 10th ed. McGraw-Hill; New York: 2001
• 2a Pestka S, Brot N. J. Biol. Chem. 1971; 246: 7715
• 2b Burns DJ. W, Cundliffe E. J. Biochem. 1973; 37: 570
• 2c Robbe Y, Fernandez JP, Chapat JP, Sentence RH, Fatome M. Eur. J. Med. Chem. 1985; 20: 16
• 2d Sharrow SD, Novotny MV, Stone M. J. Biochem. 2003; 42: 6302
• 2e Bergeron RJ, Weigand J, Dionis JB, Karmakka ME, Frej J, Tencer AH. J. Med. Chem. 1991; 34: 2072
• 2f Hawkins CJ, Lavin MF, Marshall KA, vander Brenk AL, Watters DJ. J. Med. Chem. 1990; 33: 1634
• 2g Boyce RJ, Mulqueen GC, Pattenden G. Tetrahedron Lett. 1994; 35: 5705
• 3 Mellah M, Voituriez A, Schulz E. Chem. Rev. 2007; 107: 5133
• 4a Seijas JA, Tato MP. V, Campo JC. Tetrahedron 2008; 64: 9280
• 4b Vorbruggen H, Krolikiewicz K. Tetrahedron Lett. 1981; 22: 4471
• 4c Wipf P, Wang X. J. Comb. Chem. 2002; 4: 656
• 5a Petersson MJ, Jenkins ID, Loughlin WA. Org. Biomol. Chem. 2009; 7: 739
• 5b Kodama Y, Ori M, Nishio T. Helv. Chim. Acta 2005; 88: 187
• 5c Nishio T. Tetrahedron Lett. 1995; 36: 6113
• 5d Busacca CA, Dong Y, Spinelli EM. Tetrahedron Lett. 1996; 37: 2935
• 5e Padmavathi V, Reddy BC. O, Mohan AV. N, Padmaja A. J. Heterocycl. Chem. 2007; 44: 459
• 6a Kwiatkowski S, Crocker PJ, Chavan AJ, Nobuyuki I, Haley BE, Watt DS, Ho R.-j. Tetrahedron Lett. 1990; 31: 2093
• 6b Ramasamy KS, Bandaru R, Averett DJ. J. Org. Chem. 2000; 65: 5849
• 6c Yamakuchi M, Matsunaga H, Tokuda R, Ishizuka T, Nakajima M, Kunieda T. Tetrahedron Lett. 2005; 46: 4019
• 7a Bazgir A, Amini MM, Fazaeli Y. Open Catal. J. 2009; 2: 163 ; http://benthamopen.com/tocatj/home
• 7b Baltork M.-I, Moghadam M, Tangestaninejad S, Mirkhani V, Hojati SF. Catal. Commun. 2009; 9: 1153
• 7c Baltork M.-I, Moghadam M, Tangestaninejad S, Mirkhani V, Hojati SF. Polyhedron 2008; 27: 750
• 7d Shaabani A, Seyyedhamzeh M, Maleki A, Rezazadeh F. Appl. Catal. A 2009; 358: 146
• 7e Wu L. E-J. Chem. 2012; 9: 1035 ; http://www.hindawi.com/journals/jchem/
• 7f Li X, Zhou B, Zhang J, She M, An S, Ge H, Li C, Yin B, Li J, Shi Z. Eur. J. Org. Chem. 2012; 1626
• 7g Fache F, Cros F, Piva O, Lefebvre F. Synth. Commun. 2012; 42: 2098
• 7h Lu G, Yang L, Wu L. Phosphorus, Sulfur, Silicon Relat. Elem. 2012; 187: 403
• 7i Hojati SF, Baltork M.-I, Maleki B, Gholizadeh M, Shafiezadeh F, Haghdoust M. Can. J. Chem. 2010; 88: 135
• 8 Fernandez X, Fellous R, Dunach E. Tetrahedron Lett. 2000; 41: 3381
• 9 Pathak U, Bhattacharyya S, Dhruwansh V, Pandey LK, Tank R, Suryanarayana MV. S. Green Chem. 2011; 13: 1648
• 10 Pathak U, Bhattacharyya S, Pandey LK, Mathur S, Jain R. RSC Adv. 2014; 4: 3900
• 11 Goud DR, Pathak U. Synthesis 2012; 44: 3678
• 12 Kamila S, Biehl ER. J. Heterocycl. Chem. 2007; 44: 407
• 13 Harris RL. N. Aust. J. Chem. 1974; 27: 2635
• 14 Katritzky AR, Cai C, Suzuki K, Singh SK. J. Org. Chem. 2004; 69: 811
• 15 Manjula MK. Org. Chem.: Indian J. 2008; 4: 36
• 16 Caujolle R, Favrot JD, Loiseau PR, Payard M, Amarouch H, Lazrek H, Linas MD, Seguela JP, Loiseau PM. Pharm. Acta Helv. 1991; 66: 237