One-pot multicomponent synthesis of functionalized 2,5-disubstituted-1,3,4-thiadiazine derivatives

References

• Jacobson, A. K. Platelet ADP receptor antagonists: Ticlopidine and clopidogrel. Best Pract. Res. Clin. Haematol. 2004, 17, 55–64.
   PubMed Web of Science ®Google Scholar
• Kalinski, C.; Lemoine, H.; Schmidt, J.; Burdock, C.; Kolb, J.; Umkehrer, M.; Ross, G. Multicomponent reactions as a powerful tool for generic drug synthesis. Synthesis 2008, 24, 4007–4011.
   Web of Science ®Google Scholar
• Savi, P.; Zachayus, J. L.; Delesque-Touchard, N.; Labouret, C.; Herve’, C.; Uzabiaga, M. F.; Pereillo, J. M.; Culouscou, J. M.; Bono, F.; Ferrara, P.; Herbert, J. M. The active metabolite of clopidogrel disrupts P2Y12 receptor oligomers and partitions them out of lipid rafts. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 11069–11074.
   PubMed Web of Science ®Google Scholar
• Xu, L. W.; Xia, C. G.; Li, L. Transition metal salt–catalyzed direct three-component Mannich reactions of aldehydes, ketones, and carbamates: Efficient synthesis of N-protected beta-aryl-beta-amino ketone compounds. J. Org. Chem. 2004, 69, 8482–8484.
   PubMed Web of Science ®Google Scholar
• Musonda, C. C.; Taylor, D.; Lehman, J.; Gut. J.; Rosenthal, P. J.; Chibale, K. Application of multi-component reactions to antimalarial drug discover, part 1: Parallel synthesis and antiplasmodial activity of new 4-aminoquinoline Ugi adducts. Bioorg. Med. Chem. Lett. 2004, 14, 3901–3905.
   PubMed Web of Science ®Google Scholar
• Umkehrer, M.; Kalinski, C.; Kolb, J.; Burdack, C. A new and versatile one-pot synthesis of indol-2-ones by a novel Ugi four-component Heck reaction. Tertahedron Lett. 2006, 47, 2391–2393.
   Web of Science ®Google Scholar
• Xia, Q.; Ganem, B. Metal-promoted variants of the Passerini reaction leading to functionalized heterocycles. Org. Lett. 2002, 4, 1631–1634.
   PubMed Web of Science ®Google Scholar
• Ramazani, A.; Kazemizadeh, A. R.; Ahmadi, E.; Noshiranzadeh, N.; Souldozi, A. Synthesis and reactions of stabilized phosphorus ylides. Curr. Org. Chem. 2008, 12, 59–82.
   Web of Science ®Google Scholar
• Ohno, H.; Ohta, Y.; Oishi, S.; Fujii, N. Direct synthesis of 2-(aminomethyl)indoles through copper(I)-catalyzed domino three-component coupling and cyclization reactions. Angew. Chem. Int. Ed. 2007, 46, 2295–2298.
   PubMed Web of Science ®Google Scholar
• Bonne, D.; Dekhane, M.; Zhu, J. Modulating the reactivity of a-isocyanoacetates: Multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones. Angew. Chem. Int. Ed. 2007, 46, 2485–2488.
   PubMed Web of Science ®Google Scholar
• Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. CO2 incorporation reaction using arynes: Straightforward access to benzoxazinone. J. Am. Chem. Soc. 2006, 128, 11040–11041.
   PubMed Web of Science ®Google Scholar
• Geary, L. M.; Hultin, P. G. Modular construction of 2-substituted benzo[b]furans from 1,2-dichlorovinyl ethers. Org. Lett. 2009, 11, 5478–5481.
   PubMed Web of Science ®Google Scholar
• Dudley, M. E.; Morshed, M. M.; Hossain, M. M. A convenient method of synthesizing 3-ethoxycarbonylbenzofurans from salicylaldehydes and ethyl diazoacetate. Synthesis 2006, 10, 1711–1714.
   Google Scholar
• Buu-Hoï, N. P.; Bisagni, E.; Royer, R.; Routier, C. Spasmolytic ketones in the benzofuran series, and related compounds. J. Chem. Soc. 1957, 625–628.
   Web of Science ®Google Scholar
• Schneiders, G. E.; Stevenson, R. Synthesis of (+-)-machicendiol. J. Org. Chem. 1979, 44, 4710–4711.
   Web of Science ®Google Scholar
• Santana, L.; Teijeira, M.; Uriarte, E.; Teran, C.; Linares, B.; Villar, R.; Laguna, R.; Cano, E. AM1 theoretical study, synthesis and biological evaluation of some benzofuran analogues of anti-inflammatory arylalkanoic acids. Eur. J. Pharm. Sci. 1998, 7, 161–166.
   Web of Science ®Google Scholar
• Findlay, J. A.; Buthelezi, S.; Guoqiang, L.; Michelle, S. Insect toxins from an endophytic fungus from wintergreen. J. Nat. Prod. 1997, 60, 1214–1215.
   Web of Science ®Google Scholar
• Leonardi, A.; Nava, G.; Nardi, D. Farmaco Ed. Sci. 1997, 38, 290.
   Google Scholar
• Dawood, K. M.; Gawad, H. A.; Rageb, E. A.; Ellithey, M.; Mohamed, H. A. Synthesis, anticonvulsant, and anti-inflammatory evaluation of some new benzotriazole and benzofuran-based heterocycles. Bioorg. Med. Chem. 2006, 14, 3672–3680.
   PubMed Web of Science ®Google Scholar
• Musser, J. H.; Brown, R. E.; Love, B.; Bailey, K.; Jones, H.; Kahen, R.; Huang, F. C.; Khandurala, A.; Leibowitz, M.; Goldman, S.; Ruzza, D. Synthesis of 2-(2,3-dihydro-2-oxo-1,3,4-oxadiazol-5-yl) benzo heterocycles: A novel series of orally active antiallergic agents. J. Med. Chem. 1984, 27, 121–125.
   PubMed Web of Science ®Google Scholar
• Samia, M. R.; Soad, A. M.; Hawash, Aly, A.; Mostafa, M. M.; Meligy, E. Synthesis of novel benzofuran and related benzimidazole derivatives for evaluation of in vitro anti-HIV-1, anticancer and antimicrobial activities. Arch. Pharm. Res. 2006, 29, 826–833.
   PubMed Web of Science ®Google Scholar
• Farghaly, A. A.; Vanelle, P.; El-Kashef, H. S. Synthesis, reactions, and antimicrobial activity of some new 1,3,4-oxadiazoles, 1,2,4-triazoles, and 1,3,4-thiadiazines derived from pyrazole. Heterocycl. Commun. 2005, 11, 255–262.
   Web of Science ®Google Scholar
• Miao, R.; Wei, J.; Lv, M.; Cai, Y.; Du, Y.; Hui, X.; Wang, Q. Conjugation of substituted ferrocenyl to thiadiazine as apoptosis-inducing agents targeting the Bax/Bcl-2 pathway. Eur. J. Med. Chem. 2011, 46, 5000–5009.
   PubMed Web of Science ®Google Scholar
• Sarapultsev, P.; Chupakhin, O.; Sarapultsev, A.; Rantsev, M.; Sidorova, L.; Medvedeva, S.; Danilova, I. New insights in to the treatment of myocardial infarction. Int. J. Exp. Pathol. 2012, 93, 18–23.
   PubMed Web of Science ®Google Scholar
• Sarapultsev, P. A.; Chupakhin, O. N.; Medvedeva, S. U.; Mukhlynina, E. A.; Brilliant, S. A.; Sidorova, L. P.; Danilova, I. G.; Sarapultsev, A. P. The impact of immunomodulator compound from the group of substituted thiadiazines on the course of stress reaction. Int. Immunopharmacol. 2015, 25, 440–449.
   PubMed Web of Science ®Google Scholar
• Himmel, H. M.; Amos, G. J.; Wettwer, E.; Ravens, U. Effects of the calcium sensitizer [+]-EMD 60263 and its enantiomer [−]-EMD 60264 on cardiac ionic currents of guinea pig and rat ventricular myocytes. J. Cardiovasc. Pharmacol. 1999, 33, 301–308.
   PubMed Web of Science ®Google Scholar
• Tomita, Y.; Kabashima, S.; Okawara, T.; Yamasaki, T.; Furukawa, M. Heterocyclization of 2,4-disubstituted thiosemicarbazides with haloketones. J. Heterocycl. Chem. 1990, 27, 707–710.
   Web of Science ®Google Scholar
• Bondock, S.; Tarhoni, A. El-G.; Fadda, A. A. Heterocyclic synthesis with 4-benzoyl-1-cyanoacetylthiosemicarbazide: Selective synthesis of some thiazole, triazole, thiadiazine, pyrrylthiazole, and pyrazolo[1,5-a]triazine derivatives. Monatsh. Chem. 2008, 139, 153–159.
   Web of Science ®Google Scholar
• Busby, R. E.; Dominey, T. W. The rearrangement of 2-amino-1,3,4-thiadiazines to 3-amino-2-thiazolimines, part 1: The rates of rearrangement of a series of 5-alkyl- and 5-aryl-2-amino-1,3,4-thiadiazines at 30 and 50 °C. J. Chem. Soc., Perkin Trans. 2 1980, 6, 890–899.
   Google Scholar
• Mamedov, V. A.; Berdnikov, E. A.; Valeeva, V. N.; Ismaev, I. E.; Rizvanov, I. Ch.; Antokhina, L. A.; Nuretdinov, I. A.; Chernov, P. P. Six-membered cyclic semiaminal as intermediate in the synthesis of thiazoles from thiosemicarhazide and α-haloketones. Russ. Chem. Bull. 1993, 42, 1879–1882.
   Web of Science ®Google Scholar
• Schroder, J.; Henke, A.; Wenzel, H.; Brandstetter, H.; Stammler, H. G.; Stammler, A.; Pfeiffer, W. D.; Tschesche, H. Structure-based design and synthesis of potent matrix metalloproteinase inhibitors derived from a 6H-1,3,4-thiadiazine scaffold. J. Med. Chem. 2001, 44, 3231–3243.
   PubMed Web of Science ®Google Scholar
• Sugawara, H.; Endoh, M. (–)-Enantiomer EMD 57439 antagonizes the Ca2+ sensitizing effect of (+)-enantiomer EMD 57033 on diastolic function but not on systolic function in rabbit ventricular cardiomyocytes. Jpn. J. Pharmacol. 1999, 80, 55–65.
   PubMedGoogle Scholar
• Himmel, H. M.; Amos, G. J.; Wettwer, E. U. J. Ravens, Cardiovasc. Pharmacol. 1999, 33, 301.
   PubMed Web of Science ®Google Scholar
• Eggenweiler, H. M.; Wolf, M. Ger. Patent 10,150,517, 2003; Chem. Abstr. 2003, 138, 297702; Warner, J. M. PCT Int. Appl. WO Patent 2,004,067,006, 2004; Chem. Abstr. 2004, 141, 185092.
   Google Scholar
• Ludwig, A. F.; Kippur, P. R. U. S. Patent 2,726,263, 1955; Chem. Abst. 1956, 50, 10128.
   Google Scholar
• Olin Mathieson Chemical Crop, British Patent 754,756, 1956; Chem. Abstr. 1957, 8782h.
   Google Scholar