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Articles

A convenient synthesis of thiazol-2(3H)-one skeletons from a reaction involving terminal alkynes, elemental sulfur, and isocyanates

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Pages 258-270 | Received 16 Oct 2019, Accepted 05 Dec 2019, Published online: 29 Dec 2019

References

  • Gao K, Wu J. Synthesis of Functionalized 1,2-Dihydroisoquinolines via Multicomponent One-Pot Reaction of 2-Alkynylbenzaldehyde, Amine, Zinc, and Allylic Bromide or BenzylBromide. J. Org. Chem. 2007;72:8611–8613. doi: 10.1021/jo7016839
  • Evano G, Blanchard N, Toumi M. Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis. Chem. Rev. 2008;108:3054–3131. doi: 10.1021/cr8002505
  • Potuganti GR, Indukuri DR, Nanubolu JB, et al. Copper-catalyzed Domino Addition, Hydroamination and Cyclization: A Multicomponent Approach to Spiro Oxazolidinone Derivatives. J. Org. Chem. 2018;83:15186–15190. doi: 10.1021/acs.joc.8b02461
  • Yang T, Lin C, Fu H, et al. Copper-Catalyzed Synthesis of Medium and Large-Sized Nitrogen Heterocycles via N-Arylation of Phosphoramidates and Carbamates. Organic Lett. 2005;7:4781–4784. doi: 10.1021/ol052126c
  • Guo XX, Gu DW, Wu Z, et al. Copper-Catalyzed C–H Functionalization Reactions: Efficient Synthesis of Heterocycles. Chem. Rev. 2015;11:1622–1651. doi: 10.1021/cr500410y
  • Ghazanfarpour-Darjani M, Babapour-Kooshalshahi M, Mousavi-Safavi SM, et al. Copper-Catalyzed Domino Addition-Cyclization Reaction between Terminal Alkynes, Carbon Disulfide, and Oxiranes. Synlett. 2016;27:259–261. doi: 10.1055/s-0035-1560486
  • Samzadeh-Kermani A. Silver Salt Catalyzed Synthesis of 1,4-Oxathian-3-imine Derivatives. Tetrahedron. 2016;72:5301–5303. doi: 10.1016/j.tet.2016.06.072
  • Samzadeh-Kermani A, Ghasemi S. A Catalytic Route to Pyrrole Derivatives via Copper-catalyzed Multicomponent Reaction. J. Het. Chem. 2019;56:2202–2209. doi: 10.1002/jhet.3614
  • Meldal M, Tornøe CW. Cu-Catalyzed Azide-Alkyne Cycloaddition. Chem. Rev. 2008;108:2952–3015. doi: 10.1021/cr0783479
  • Ranjan A, Mandal A, Yerande SG, et al. Asymmetric Alkynylation/Hydrothiolation Cascade: Enantioselec tive Synthesis of Thiazolidine-2-imines from Imine, Acetylene and Isothiocyanate. Chem. Commun. 2015;51:14215–14219. doi: 10.1039/C5CC05549K
  • Knöpfel TF, Carreira EM. The First Conjugate Addition Reaction of Terminal Alkynes Catalytic in Copper: Conjugate Addition of Alkynes in Water. J. Am. Chem. Soc. 2003;125:6054–6055. doi: 10.1021/ja035311z
  • Varmazyar A, Nozad Goli-Kand A, Sedaghat S, et al. Copper Salt Catalyzed Synthesis of Functionalized 2H-Pyranes. J. Heterocyclic Chem. 2019;56:1850–1856. doi: 10.1002/jhet.3570
  • Varmazyar A, Nozad Goli-Kand A, Sedaghat S, Khalaj M, Arab-Salmanabadi S. Domino ring opening/cyclization of oxiranes for synthesis of functionalized 2H-pyran-5-carboxylate. 2019..
  • Li C, Mo F, Li W, et al. AuPPh3Cl/AgOTf-catalyzed reaction of terminal alkynes: nucleophilic addition to activated CO bond. Tetrahedron Letters. 2009;50:6053–6056. doi: 10.1016/j.tetlet.2009.08.049
  • Dorel R, Echavarren AM. Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity. Chem. Rev. 2015;115:9028–9072. doi: 10.1021/cr500691k
  • Mayer R, Gewald K. The Action of Carbon Disulfide and Sulfur on Enamines. Ketimines, and CH Acids. Angew. Chem. internat. Edit. 1967;6:294–306. doi: 10.1002/anie.196702941
  • Khalaj M, Sadeghpour M, Mousavi Safavi SM, et al. Copper-catalyzed synthesis of thiazolidine derivatives via multicomponent reaction of terminal alkynes, elemental sulfur, and aziridines. Monatshefte für Chemie – Chemical Monthly. 2019;150:1085–1091. doi: 10.1007/s00706-019-2363-7
  • Samzadeh-Kermani A. A Novel Three-Component Reaction Involving Terminal Alkynes, Elemental Sulfur, and Strained Heterocycles. Synlett. 2015;26:643–645. doi: 10.1055/s-0034-1379949
  • Jin Q, Fu Z, Guan L, et al. Syntheses of Benzo[d]Thiazol-2(3H)-One Derivatives and Their Antidepressant and Anticonvulsant Effects. Mar. Drugs. 2019;17:430–439. doi: 10.3390/md17070430
  • Wang S, Chen Y, Zhao S, et al. Synthesis and biological evaluation of a series of benzoxazole/benzothiazole-containing 2,3-dihydrobenzo[b][1,4] dioxine derivatives as potential antidepressants. Bioorg. Med. Chem. Lett. 2014;24:1766–1770. doi: 10.1016/j.bmcl.2014.02.031
  • Liu DC, Zhang HJ, Jin CM, et al. Synthesis and biological evaluation of novel benzothiazole derivatives as potential anticonvulsant agents. Molecules. 2016;21:1635–1652. doi: 10.3390/molecules21121635
  • Nicolaou KC, Yin J, Mandal D, et al. Total Synthesis and Biological Evaluation of Natural and Designed Tubulysins. J. Am. Chem. Soc. 2016;138:698–1708.
  • Wilson ZE, Fenner S, Ley SV. Total syntheses of linear polythiazole/oxazole plantazolicin A and its biosynthetic precursor plantazolicin B. Angew. Chem. Int. Ed. 2015;54:1284–1288. doi: 10.1002/anie.201410063
  • Fürstner A, Langemann K. Total Syntheses of (+)-Ricinelaidic Acid Lactone and of (−)-Gloeosporone Based on Transition-Metal-Catalyzed C−C Bond Formations. J. Am. Chem. Soc. 1997;119:9130–9136. doi: 10.1021/ja9719945
  • Rist Q, Grimstrup M, Receveur JM, et al. Novel selective thiazoleacetic acids as CRTH2 antagonists developed from in silico derived hits. Part 1. Bioorganic & Medicinal Chemistry Letters. 2010;20:1177–1180. doi: 10.1016/j.bmcl.2009.12.008
  • Wipf P, Venkatraman S. A New Thiazole Synthesis by Cyclocondensation of Thioamides and Alkynyl(Aryl)Iodonium Reagents. J. Org. Chem. 1996;61:8004–8005. doi: 10.1021/jo961681c
  • Weiß KM, Wei S, Tsogoeva SB. Novel one-pot process for the synthesis of 1,3-thiazolesvia organocatalysed epoxidation of nitro-olefins. Org. Biomol. Chem. 2011;9:3457–3461. doi: 10.1039/c1ob05260h
  • Ghazanfarpour-Darjani M, Khodakarami A. Organocatalytic one-pot synthesis of functionalized 1,3-oxathiolanes and 1,3-thiazolidines. Monatshefte für Chemie – Chemical Monthly. 2016;147:829–835. doi: 10.1007/s00706-015-1543-3
  • Alizadeh-Bami F, Mehrabi H, Ranjbar-Karimi R. One-pot three-component reaction of arylglyoxals with acetylthiourea and Meldrum’s acid or barbituric acid for synthesis of new 2-acetamido-4-arylthiazol-5-yl derivatives. Journal of Sulfur Chemistry. 2019;40:469–478. doi: 10.1080/17415993.2019.1602127
  • Saroha M, Khurana JM. Acetic acid mediated regioselective synthesis of 2,4,5-trisubstituted thiazoles by a domino multicomponent reaction. New J. Chem. 2019;43:8644–8650. doi: 10.1039/C9NJ01717H
  • Vishwanatha TV, Kurpiewska K, Kalinowska-Tłusćik J, et al. Cysteine Isocyanide in Multicomponent Reaction: Synthesis of Peptido-Mimetic 1,3-Azoles. J. Org. Chem. 2017;82:9585–9594. doi: 10.1021/acs.joc.7b01615
  • Mahesh TC, Shivani P, Palmi M, et al. Thiazole: A Review on Chemistry, Synthesis and Therapeutic Importance of its Derivatives. Current Topics in Medicinal Chemistry. 2016;16:2841–2862. doi: 10.2174/1568026616666160506130731
  • Nguyen TB, Retailleau P. Sulfur-Promoted Decarboxylative Sulfurative Hexamerization of Phenylacetic Acids: Direct Approach to Hexabenzylidyne Tetrasulfides. Org. Lett. 2019;21:279–282. doi: 10.1021/acs.orglett.8b03728
  • Nguyen TB, Retailleau P. Cooperative Activating Effect of Tertiary Amine/DMSO on Elemental Sulfur: Direct Access to Thioaurones from 2′-Nitrochalcones under Mild Conditions. Org. Lett. 2018;20:186–189. doi: 10.1021/acs.orglett.7b03547
  • Nguyen TB, Retailleau P. Sulfurative self-condensation of ketones and elemental sulfur: a three-component access to thiophenes catalyzed by aniline acid–base conjugate pairs. Green Chem. 2018;20:387–390. doi: 10.1039/C7GC03437G
  • Nguyen TB, Retailleau P. DIPEA-Promoted Reaction of 2-Nitrochalcones with Elemental Sulfur: An Unusual Approach to 2-Benzoylbenzothiophenes. Org. Lett. 2017;19:4858–4860. doi: 10.1021/acs.orglett.7b02321
  • Nguyen LA, Ngo QA, Retailleauc P, et al. Elemental sulfur as a polyvalent reagent in redox condensation with o-chloronitrobenzenes and benzaldehydes: three-component access to 2-arylbenzothiazoles. Green Chem. 2017;19:4289–4293. doi: 10.1039/C7GC01825H
  • Nguyen TB. Recent Advances in Organic Reactions Involving Elemental Sulfur. Adv. Synth. Catal. 2017;359:1066–1130. doi: 10.1002/adsc.201601329
  • Nguyen TB, Pasturaud K, Ermolenko L, et al. Concise Access to 2-Aroylbenzothiazoles by Redox Condensation Reaction between o-Halonitrobenzenes, Acetophenones, and Elemental Sulfur. Org. Lett. 2015;17:2562–2565. doi: 10.1021/acs.orglett.5b01182
  • Samzadeh-Kermani A. Copper Catalyzed Synthesis of Thiomorpholine Derivatives: A New Entry of Multicomponent Reaction Between Terminal Alkynes, Isothiocyanates, and Aziridines. J. Het. Chem. 2019;56:450–455. doi: 10.1002/jhet.3418
  • Samzadeh-Kermani A. Silver Iodide Catalyzed Three-Component Reaction between Terminal Alkynes, Carbon Disulfide, and Aziridines. Journal of Sulfur Chemistry. 2019;40:554–564. doi: 10.1080/17415993.2019.1631316

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