How to cite this paper
Sinenko, V., Slivchuk, S & Brovarets, V. (2018). Lithiation of 2-bromo-4-(1,3-dioxolan-2-yl)-1,3-thiazole.Current Chemistry Letters, 7(1), 1-8.
Refrences
1. Giroud M., Ivkovic J., Martignoni M., Fleuti M., Trapp N., Haap W., Kuglstatter A., Benz J., Kuhn B., Schirmeister T., Diederich F. (2017) Inhibition of the Cysteine Protease Human Cathepsin L by Triazine Nitriles: Amide Heteroarene π-Stacking Interactions and Chalcogen Bonding in the S3 Pocket. Chem. Med. Chem., 12 (3) 257-270.
2. Suzuki T., Muto N., Bando M., Itoh Y., Masaki A., Ri M., Ota Y., Nakagawa H., Iida S., Shirahige K., Miyata N. (2014) Design, Synthesis, and Biological Activity of NCC149 Derivatives as Histone Deacetylase 8-Selective Inhibitors. Chem. Med. Chem., 9 (3) 657-664.
3. Murphy J. M., Armijo A. L., Nomme J., Lee C. H., Smith Q. A., Li Z., Campbell D. O., Liao H.-I., Nathanson D. A., Austin W. R., Lee J. T., Darvish R., Wei L., Wang J., Su Y., Damoiseaux R., Sadeghi S., Phelps M. E., Herschman H. R., Czernin J., Alexandrova A.N., Jung M. E., Lavie A., Radu C. G. (2013) Development of New Deoxycytidine Kinase Inhibitors and Noninvasive in Vivo Evaluation Using Positron Emission Tomography. J. Med. Chem., 56 (17) 6696-6709.
4. James D. I., Smith K. M., Jordan A. M., Fairweather E. E., Griffiths L. A., Hamilton N. S., Hitchin J. R., Hutton C. P., Jones S., Kelly P., McGonagle A. E., Small H., Stowell A. J., Tucker J., Waddell I. D., Waszkowycz B., Ogilvie D. J. (2016) First-in-class chemical probes against poly(ADP-ribose) glycohydrolase (PARG) inhibit DNA repair with differential pharmacology to olaparib. ACS Chem. Biol., 11 (11) 3179-3214.
5. Sznaidman M. L., Haffner C. D., Maloney P. R., Fivush A., Chao E., Goreham D., Sierra M. L., LeGrumelec C., Xu H. E., Montana V. G., Lambert M. H., Willson T. M., Oliver W. R. Jr., Sternbach D. D. (2003) Novel Selective Small Molecule Agonists for Peroxisome Proliferator-Activated Receptorδ (PPAR δ) - Synthesis and Biological Activity. Bioorg. Med. Chem. Lett., 13 (9) 1517-1521.
6. Wei Z., Kozikowski A. P. (2003) A Short and Efficient Synthesis of the Pharmacological Research Tool GW501516 for the Peroxisome Proliferator-Activated Receptor δ. J. Org. Chem., 68 (23) 9116-9118.
7. Louvel J., Guo D., Soethoudt M., Mocking T., Lenselink E.B., Mulder-Krieger T., Heitman L. H., Ijzerman A. P. (2015) Structure-kinetics relationships of Capadenoson derivatives as adenosine A1 receptor agonists. Eur. J. Med. Chem., 101 681-691.
8. Brunschweiger A., Koch P., Schlenk M., Rafehi M., Radjainia H., Küppers P., Hinz S., Pineda F., Wiese M., Hockemeyer J., Heer J., Denonne F., Müller C. E. (2016) 8-Substituted 1,3-dimethyltetrahydropyrazino[2,1-f]purinediones: Water-soluble adenosine receptor antagonists and monoamine oxidase B inhibitors. Bioorg. Med. Chem., 24 (21) 5462-5481.
9. Siegrist R., Pozzi D., Jacob G., Torrisi C., Colas K., Braibant B., Mawet J., Pfeifer T., DeKanter R., Roch C., Kessler M., Corminboeuf O., Bezençon O. (2016) Structure-Activity Relationship, Drug Metabolism and Pharmacokinetics Properties Optimization, and in Vivo Studies of New Brain Penetrant Triple T-Type Calcium Channel Blockers. J.Med. Chem., 59 (23) 10661-10675.
10. Cockerill G. S., Lackey K. E. (2005) Anilinoquinazolines as proteintyrosine kinase inhibitors. US Patent 6933299B1.
11. Athmani S., Bruce A., lddon B. (1992) Azoles. Part 8. Metallation and Bromine-Lithium Exchange Reactions of Polyhalogenothiazoles. J. Chem. Soc. Perkin Trans. I, 2 215-219.
12. Dillender S. C., Greenwood T. D., Hendi M. S., Wolfe J. F. (1986) Reactions of 2-Halothiazoles with Ketone Enolates and Nitrile Carbanions. J. Org. Chem., 51 (8) 1184-1188.
13. Katritzky A. R., Laurenz K. S., Relyea D. I. (1988) The preparation and fungicidal activity of a series of thiazolyl- and isothiazolyl-diarylcarbinols. Can. J. Chem., 66 (7) 1617-1624.
14. Tsutsumi S., Okonogi T., Shibahara S., Ohuchi S., Hatsushiba E., Patchett A. A. Christensen B. G. (1994) Synthesis and Structure-Activity Relationships of Peptidyl a-Keto Heterocycles as Novel Inhibitors of Prolyl Endopeptidase. J. Med. Chem., 37 (21) 3492-3502.
15. Dunst C., Knochel P. (2011) Regioselective Functionalization of the Thiazole Scaffold Using TMPMgCl·LiCl and TMP2Zn·2MgCl2·2LiCl. J. Org. Chem., 76 (16) 6972–6978.
16. Kienle M., Dunst C., Knoche P. (2009) Oxidative Amination of Heteroaromatic Zinc Reagents Mediated by PhI(OAc)2. Org. Lett., 11 (22) 5158-5161.
17. Dunst C., Kienle M., Knoche P. (2010) Preparation of Heterocyclic Amines via a Copper(I)-Mediated Oxidative Cross-Coupling of Organozinc Reagents with Lithium Amides. Synthesis, 13 2313–2318.
18. Wunderlih S. H., Knochel P. (2007) (tmp)2Zn·2MgCl2·2LiCl: A Chemoselective Base for the Directed Zincation of Sensitive Arenes and Heteroarenes. Angew. Chem. Int. Ed., 46 (40) 7685–7688.
19. McDonald S. L, Hendrick C.E., Wang Q. (2014) Copper-Catalyzed Electrophilic Amination of Heteroarenes and Arenes by C-H Zincation. Angew. Chem. Int. Ed., 53 (18) 4667-4670.
20. Sinenko V. O., Slivchuk S. R., Mityukhin O. P., Brovarets V. S. (2017) Synthesis of new 1,3-thiazolecarbaldehydes. Zh. Obshch. Khim., 87 (12) 1947-1956.
21. Zambon A., Borsato G., Brussolo S., Frascella P. Lucchini V. (2008) Efficient access to 5-substituted thiazoles by a novel metallotropic rearrangement. Tetrahedron Lett., 49 (1) 66–69.
22. Stanetty P., Schnurch M., Mereiter K., Mihovilovic M. D. (2005) Investigations of the Halogen Dance Reaction on N-Substituted 2-Thiazolamines. J. Org. Chem., 70 (2) 567-574.
23. Stangeland E. L., Sammakia T. (2004) Use of Thiazoles in the Halogen Dance Reaction: Application to the Total Synthesis of WS75624B. J. Org. Chem., 69 (7) 2381-2385.
2. Suzuki T., Muto N., Bando M., Itoh Y., Masaki A., Ri M., Ota Y., Nakagawa H., Iida S., Shirahige K., Miyata N. (2014) Design, Synthesis, and Biological Activity of NCC149 Derivatives as Histone Deacetylase 8-Selective Inhibitors. Chem. Med. Chem., 9 (3) 657-664.
3. Murphy J. M., Armijo A. L., Nomme J., Lee C. H., Smith Q. A., Li Z., Campbell D. O., Liao H.-I., Nathanson D. A., Austin W. R., Lee J. T., Darvish R., Wei L., Wang J., Su Y., Damoiseaux R., Sadeghi S., Phelps M. E., Herschman H. R., Czernin J., Alexandrova A.N., Jung M. E., Lavie A., Radu C. G. (2013) Development of New Deoxycytidine Kinase Inhibitors and Noninvasive in Vivo Evaluation Using Positron Emission Tomography. J. Med. Chem., 56 (17) 6696-6709.
4. James D. I., Smith K. M., Jordan A. M., Fairweather E. E., Griffiths L. A., Hamilton N. S., Hitchin J. R., Hutton C. P., Jones S., Kelly P., McGonagle A. E., Small H., Stowell A. J., Tucker J., Waddell I. D., Waszkowycz B., Ogilvie D. J. (2016) First-in-class chemical probes against poly(ADP-ribose) glycohydrolase (PARG) inhibit DNA repair with differential pharmacology to olaparib. ACS Chem. Biol., 11 (11) 3179-3214.
5. Sznaidman M. L., Haffner C. D., Maloney P. R., Fivush A., Chao E., Goreham D., Sierra M. L., LeGrumelec C., Xu H. E., Montana V. G., Lambert M. H., Willson T. M., Oliver W. R. Jr., Sternbach D. D. (2003) Novel Selective Small Molecule Agonists for Peroxisome Proliferator-Activated Receptorδ (PPAR δ) - Synthesis and Biological Activity. Bioorg. Med. Chem. Lett., 13 (9) 1517-1521.
6. Wei Z., Kozikowski A. P. (2003) A Short and Efficient Synthesis of the Pharmacological Research Tool GW501516 for the Peroxisome Proliferator-Activated Receptor δ. J. Org. Chem., 68 (23) 9116-9118.
7. Louvel J., Guo D., Soethoudt M., Mocking T., Lenselink E.B., Mulder-Krieger T., Heitman L. H., Ijzerman A. P. (2015) Structure-kinetics relationships of Capadenoson derivatives as adenosine A1 receptor agonists. Eur. J. Med. Chem., 101 681-691.
8. Brunschweiger A., Koch P., Schlenk M., Rafehi M., Radjainia H., Küppers P., Hinz S., Pineda F., Wiese M., Hockemeyer J., Heer J., Denonne F., Müller C. E. (2016) 8-Substituted 1,3-dimethyltetrahydropyrazino[2,1-f]purinediones: Water-soluble adenosine receptor antagonists and monoamine oxidase B inhibitors. Bioorg. Med. Chem., 24 (21) 5462-5481.
9. Siegrist R., Pozzi D., Jacob G., Torrisi C., Colas K., Braibant B., Mawet J., Pfeifer T., DeKanter R., Roch C., Kessler M., Corminboeuf O., Bezençon O. (2016) Structure-Activity Relationship, Drug Metabolism and Pharmacokinetics Properties Optimization, and in Vivo Studies of New Brain Penetrant Triple T-Type Calcium Channel Blockers. J.Med. Chem., 59 (23) 10661-10675.
10. Cockerill G. S., Lackey K. E. (2005) Anilinoquinazolines as proteintyrosine kinase inhibitors. US Patent 6933299B1.
11. Athmani S., Bruce A., lddon B. (1992) Azoles. Part 8. Metallation and Bromine-Lithium Exchange Reactions of Polyhalogenothiazoles. J. Chem. Soc. Perkin Trans. I, 2 215-219.
12. Dillender S. C., Greenwood T. D., Hendi M. S., Wolfe J. F. (1986) Reactions of 2-Halothiazoles with Ketone Enolates and Nitrile Carbanions. J. Org. Chem., 51 (8) 1184-1188.
13. Katritzky A. R., Laurenz K. S., Relyea D. I. (1988) The preparation and fungicidal activity of a series of thiazolyl- and isothiazolyl-diarylcarbinols. Can. J. Chem., 66 (7) 1617-1624.
14. Tsutsumi S., Okonogi T., Shibahara S., Ohuchi S., Hatsushiba E., Patchett A. A. Christensen B. G. (1994) Synthesis and Structure-Activity Relationships of Peptidyl a-Keto Heterocycles as Novel Inhibitors of Prolyl Endopeptidase. J. Med. Chem., 37 (21) 3492-3502.
15. Dunst C., Knochel P. (2011) Regioselective Functionalization of the Thiazole Scaffold Using TMPMgCl·LiCl and TMP2Zn·2MgCl2·2LiCl. J. Org. Chem., 76 (16) 6972–6978.
16. Kienle M., Dunst C., Knoche P. (2009) Oxidative Amination of Heteroaromatic Zinc Reagents Mediated by PhI(OAc)2. Org. Lett., 11 (22) 5158-5161.
17. Dunst C., Kienle M., Knoche P. (2010) Preparation of Heterocyclic Amines via a Copper(I)-Mediated Oxidative Cross-Coupling of Organozinc Reagents with Lithium Amides. Synthesis, 13 2313–2318.
18. Wunderlih S. H., Knochel P. (2007) (tmp)2Zn·2MgCl2·2LiCl: A Chemoselective Base for the Directed Zincation of Sensitive Arenes and Heteroarenes. Angew. Chem. Int. Ed., 46 (40) 7685–7688.
19. McDonald S. L, Hendrick C.E., Wang Q. (2014) Copper-Catalyzed Electrophilic Amination of Heteroarenes and Arenes by C-H Zincation. Angew. Chem. Int. Ed., 53 (18) 4667-4670.
20. Sinenko V. O., Slivchuk S. R., Mityukhin O. P., Brovarets V. S. (2017) Synthesis of new 1,3-thiazolecarbaldehydes. Zh. Obshch. Khim., 87 (12) 1947-1956.
21. Zambon A., Borsato G., Brussolo S., Frascella P. Lucchini V. (2008) Efficient access to 5-substituted thiazoles by a novel metallotropic rearrangement. Tetrahedron Lett., 49 (1) 66–69.
22. Stanetty P., Schnurch M., Mereiter K., Mihovilovic M. D. (2005) Investigations of the Halogen Dance Reaction on N-Substituted 2-Thiazolamines. J. Org. Chem., 70 (2) 567-574.
23. Stangeland E. L., Sammakia T. (2004) Use of Thiazoles in the Halogen Dance Reaction: Application to the Total Synthesis of WS75624B. J. Org. Chem., 69 (7) 2381-2385.