253
Views
7
CrossRef citations to date
0
Altmetric
Articles

Rapid and highly efficient synthesis of thioureas in biocompatible basic choline hydroxide

&
Pages 548-554 | Received 18 Jan 2017, Accepted 02 May 2017, Published online: 23 May 2017

References

  • Chauhan K, Sharma M, Singh P, et al. Discovery of a new class of dithiocarbamates and rhodanine scaffolds as potent antifungal agents: synthesis, biology and molecular docking. MedChemComm. 2012;3:1104–1110. doi: 10.1039/c2md20109g
  • Kumar D, Sonawane M, Pujala B, et al. Supported protic acid-catalyzed synthesis of 2,3-disubstituted thiazolidin-4-ones: enhancement of the catalytic potential of protic acid by adsorption on solid supports. Green Chem. 2013;15:2872–2884. doi: 10.1039/c3gc41218k
  • Kommi DN, Kumar D, Chakraborti AK. “All water chemistry” for a concise total synthesis of the novel class anti-anginal drug (RS), (R), and (S)-ranolazine. Green Chem. 2013;15:756–767. doi: 10.1039/c3gc36997h
  • Abelló S, Medina F, Rodríguez X, et al. Supported choline hydroxide (ionic liquid) as heterogeneous catalyst for aldol condensation reactions. Chem Commun. 2004;1096–1097. doi: 10.1039/B401448K
  • Lakshmi Kantam M, Sudarshan Reddy R, Pal U, et al. Transfer hydrogenation of carbonyl compounds catalyzed by ruthenium nanoparticles stabilized on nanocrystalline magnesium oxide by ionic liquids. Adv Synth Catal. 2008;350:2231–2235. doi: 10.1002/adsc.200800342
  • Fan M, Huang J, Yang J, et al. Biodiesel production by transesterification catalyzed by an efficient choline ionic liquid catalyst. Appl Energy. 2013;108:333–339. doi: 10.1016/j.apenergy.2013.03.063
  • Zhu A, Bai S, Li L, et al. Choline hydroxide: an efficient and biocompatible basic catalyst for the synthesis of biscoumarins under mild conditions. Catal Lett. 2015;145:1089–1093. doi: 10.1007/s10562-015-1487-6
  • Lu W, Ma J, Hu J, et al. Choline hydroxide promoted chemical fixation of CO2 to quinazoline-2,4(1H,3H)-diones in water. RSC Adv. 2014;4:50993–50997. doi: 10.1039/C4RA08551E
  • Vadagaonkar KS, Kalmode HP, Prakash S, et al. Greener [3+3] tandem annulation–oxidation approach towards the synthesis of substituted pyrimidines. N J Chem. 2015;39:3639–3645. doi: 10.1039/C4NJ02345E
  • Azizi N, Edrisi M. Biodegradable choline hydroxide promoted environmentally benign thiolysis of epoxides. Tetrahedron Lett. 2016;57:525–528. doi: 10.1016/j.tetlet.2015.12.080
  • Pereira MDF, Picot L, Guillon J, et al. Efficient synthesis of novel pentacyclic 6,7-dihydro-5a,7a,13,14-tetraaza-pentaphene-5,8-diones. Tetrahedron Lett. 2005;46:3445–3447. doi: 10.1016/j.tetlet.2005.03.133
  • Maki T, Tsuritani T, Yasukata T. A mild method for the synthesis of carbamate-protected guanidines using the burgess reagent. Org Lett. 2014;16:1868–1871. doi: 10.1021/ol5002208
  • Schreiner PR. Metal-free organocatalysis through explicit hydrogen bonding interactions. Chem Soc Rev. 2003;32:289–296. doi: 10.1039/b107298f
  • Cho E, Kim TH. Direct asymmetric aldol reaction co-catalyzed by l-proline and isothiouronium salts. Tetrahedron Lett. 2014;55:6470–6473. doi: 10.1016/j.tetlet.2014.10.009
  • Lutete LM, Miyamoto T, Ikemoto T. Tertiary amino thiourea-catalyzed asymmetric cross aldol reaction of aryl methyl ketones with aryl trifluoromethyl ketones. Tetrahedron Lett. 2016;57:1220–1223. doi: 10.1016/j.tetlet.2016.02.001
  • Fukata Y, Asano K, Matsubara S. Asymmetric synthesis of 1,3-oxazolidines via intramolecular Aza-Michael addition by bifunctional organocatalysts. Chem Lett. 2013;42:355–357. doi: 10.1246/cl.121245
  • Chikushi N, Nishikami Y, Nishide H. Interaction of tris(2-aminoethyl)amine-based ureas and thiourea with superoxide anion and peroxide dianion through multiple hydrogen bonding. Chem Lett. 2014;43:760–762. doi: 10.1246/cl.140038
  • Yuan YX, Wang L, Han YF, et al. A novel azo-thiourea based visible light switchable anion receptor. Tetrahedron Lett. 2016;57:878–882. doi: 10.1016/j.tetlet.2016.01.037
  • Azizi N, Saidi MR. Lithium perchlorate diethyl ether solution: A highly efficient media for the Abramov reaction. Phosphorus Sulfur Silicon Relat Elem. 2003;178:1255–1259. doi: 10.1080/10426500307904
  • Katritzky AR, Ledoux S, Witek RM, et al. 1-(Alkyl/Arylthiocarbamoyl)benzotriazoles as stable isothiocyanate equivalents: synthesis of Di- and trisubstituted thioureas. J Org Chem. 2004;69:2976–2982. doi: 10.1021/jo035680d
  • Sharma S. Thiophosgene in organic synthesis. Synthesis. 1978:803–820. doi: 10.1055/s-1978-24896
  • Varun BV, Prabhu KR. A non-isothiocyanate route to synthesize trisubstituted thioureas of arylamines using in situ generated dithiocarbamates. RSC Adv. 2013;3:3079–3087. doi: 10.1039/c2ra23257j
  • Chau C-M, Chuan T-J, Liu K-M. A highly efficient one-pot method for the synthesis of thioureas and 2-imino-4-thiazolidinones under microwave conditions. RSC Adv. 2014;4:1276–1282. doi: 10.1039/C3RA46270F
  • Azizi N, Khajeh-Amiri A, Ghafuri H, et al. Toward a practical and waste-free synthesis of thioureas in water. Mol Divers. 2011;15:157–161. doi: 10.1007/s11030-010-9236-7
  • Kidwai M, Venkataramanan R, Dave B. Solventless synthesis of thiohydantoins over K2CO3. Green Chem. 2001;3:278–279. doi: 10.1039/b106034c
  • Gan SF, Wan JP, Pan YJ, et al. Highly efficient and catalyst-free synthesis of substituted thioureas in water. Mol Divers. 2011;15:809–815. doi: 10.1007/s11030-010-9298-6
  • Kumavat PP, Jangale AD. Green synthesis of symmetrical N, N0-disubstituted thiourea derivatives in water using solar energy. Environ Chem Lett. 2013;11:177–182. doi: 10.1007/s10311-012-0394-y
  • Maddani MR, Prabhu KR. A concise synthesis of substituted thiourea derivatives in aqueous medium. J Org Chem. 2010;75:2327–2332. doi: 10.1021/jo1001593
  • Sahu S, Sahoo R, Patel S, et al. Oxidation of thiourea and substituted thioureas: a review. J Sulfur Chem. 2011;32:171–197. doi: 10.1080/17415993.2010.550294
  • Liang F, Tan J, Piao C, et al. Carbon tetrabromide promoted reaction of amines with carbon disulfide: facile and efficient synthesis of thioureas and thiuram disulfides. Synthesis. 2008;2008:3579–3584. doi: 10.1055/s-0028-1083199
  • Halimehjani AZ, Farahbakhsh F. Synthesis of thioureas in ionic liquid medium. J Sulfur Chem. 2013;34:284–288. doi: 10.1080/17415993.2012.739623
  • Jangale AD, Kumavat PP, Wagh YB, et al. Green process development for the synthesis of aliphatic symmetrical N,N′-disubstituted thiourea derivatives in aqueous medium. Synth Commun. 2015;45:236–244. doi: 10.1080/00397911.2014.960939
  • Azizi N, Gholibeglo E. A highly efficient synthesis of dithiocarbamates in green reaction media. RSC Adv. 2012;2:7413–7416. doi: 10.1039/c2ra20615c
  • Azizi N, Mirmashhori B, Saidi MR. Lithium perchlorate promoted highly regioselective ring opening of epoxides under solvent-free conditions. Catal Commun. 2007;8:2198–2203. doi: 10.1016/j.catcom.2007.04.032
  • Azizi N, Ebrahimi F, Aakbari E, et al. Waste-free and environment-friendly uncatalyzed synthesis of dithiocarbamates under solvent-free conditions. Synlett. 2007;2007:2797–2800. doi: 10.1055/s-2007-991085
  • Azizi N, Aryanasab F, Torkiyan L. One-pot synthesis of dithiocarbamates accelerated in water. J Org Chem. 2006;71:3634–3635. doi: 10.1021/jo060048g

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.