1,3,5-Trithianes and sulfur monochloride/sodium sulfide: an alternative route to 3,5-disubstituted 1,2,4-trithiolanes

References

• Vazquez-Prieto MA, Miatello RM. Organosulfur compounds and cardiovascular disease. Mol Aspects Med. 2010;31:540–545. doi: 10.1016/j.mam.2010.09.009
   PubMed Web of Science ®Google Scholar
• Parcell S. Sulfur in human nutrition and applications in medicine. Altern Med Rev. 2002;7:22–44.
   PubMedGoogle Scholar
• Angeli A, Tanini D, Capperucci A, et al. Synthesis of different thio-scaffolds bearing sulfonamide with subnanomolar carbonic anhydrase II and IX inhibitory properties and X-ray investigations for their inhibitory mechanism. Bioorg Chem. 2018;81:642–648. doi: 10.1016/j.bioorg.2018.09.028
   PubMed Web of Science ®Google Scholar
• Tanini D, Capperucci A, Supuran CT, et al. Sulfur, selenium and tellurium containing amines act as effective carbonic anhydrase activators. Bioorg Chem. 2019;87:516–522. doi: 10.1016/j.bioorg.2019.03.062
   PubMed Web of Science ®Google Scholar
• Viglianisi C, Vasa K, Menichetti S, et al. Ditocopheryl sulfides and disulfides: synthesis and antioxidant profile. Chem Eur J. 2019;25:9108–9116. doi: 10.1002/chem.201901537
   PubMed Web of Science ®Google Scholar
• Devendar P, Yang G. Sulfur-containing agrochemicals. Top Curr Chem. 2017;375:82. DOI:10.1007/s41061-017-0169-9 and references cited therein.
   Web of Science ®Google Scholar
• Liu Y-C, Qu R-Y, Chen Q, et al. Efficient synthesis of functionalized 6-substituted-thiosalicylates via microwave-promoted Suzuki cross-coupling reaction. Tetrahedron Lett. 2007;48:6048–6050. doi: 10.1016/j.tetlet.2007.06.074
   Google Scholar
• Block E. Garlic and other alliums: the lore and the science. Cambridge, U.K.: RSC Publishing; 2010; and references cited therein.
   Google Scholar
• Qian MC, Fan X, Mahattanatawee K. Volatile sulfur compounds in food. ACS symposium series. Washington (DC): ACS Books; 2011.
   Google Scholar
• Mottram DS, Mottram HR, editors. An overview of the contribution of sulfur-containing compounds to the aroma in heated foods. ACS symposium series. Washington (DC): ACS Books; 2002.
   Google Scholar
• Wang DY, Guo W, Yongzhu F. Organosulfides: an emerging class of cathode materials for rechargeable lithium batteries. Acc Chem Res. 2019;52:2290–2300. doi: 10.1021/acs.accounts.9b00231
   PubMed Web of Science ®Google Scholar
• Mutlu H, Theato P, et al. Sulfur chemistry in polymer and materials science. Macromol Rapid Commun. 2019;40:1800650. doi:10.1002/marc.201800650.
   Web of Science ®Google Scholar
• Capperucci A, Tanini D, Degl’Innocenti A, et al. Thiosilane and organoselenosilane-mediated novel access to 3,7-disubstituted-1,2,5-trithiepanes and -1,2,5-dithiaselenepanes. Heteroat Chem. 2014;25:678–683. doi: 10.1002/hc.21157
   Web of Science ®Google Scholar
• Capperucci A, Salles C, Tanini D, et al. Selective access to sulfurated and selenated heterocycles by intramolecular cyclization of β-substituted sulfides and selenides. Phosphorus Sulfur Silicon Relat Elem. 2017;192:172–174. doi: 10.1080/10426507.2016.1252364
   Web of Science ®Google Scholar
• Mloston G, Capperucci A, Tanini D, et al. Dialkyl dicyanofumarates as oxidizing reagents for the conversion of thiols into disulfides and selenols into diselenides. Eur J Org Chem. 2017;2017:6831–6839. doi: 10.1002/ejoc.201701066
   Web of Science ®Google Scholar
• Obijalska E, Pawelec M, Mlostoń M, et al. A remarkable influence of a trifluoromethyl group on the reactions of β-mercaptoalcohols with fluorinated α-bromoenones. Eur J Org Chem. 2018;2018:3716–3723. doi: 10.1002/ejoc.201701752
   Web of Science ®Google Scholar
• Tanini D, Ermini E, Capperucci A. Seleno-michael reaction of stable functionalised alkyl selenols: a versatile tool for the synthesis of acyclic and cyclic unsymmetrical alkyl and vinyl selenides. Adv Synth Catal. 2019;361:2337–2346. doi: 10.1002/adsc.201900168
   Web of Science ®Google Scholar
• Tanini D, Lupori B, Malevolti G, et al. Direct biocatalysed synthesis of first sulfur-, selenium- and tellurium- containing L-ascorbyl hybrid derivatives with radical trapping and GPx-like properties. Chem Commun. 2019;55:5705–5708. doi: 10.1039/C9CC02427A
   PubMed Web of Science ®Google Scholar
• Tanini D, D’Esopo V, Tatini D, et al. Selenated and sulfurated analogues of triacyl glycerols: selective synthesis and structural characterization. Chem Eur J. 2020;26:2719–2725. doi: 10.1002/chem.201904686
   PubMed Web of Science ®Google Scholar
• Mlostoń G, Romański J, Weigand W, et al. Organic and coordination chemistry of 1,2,4-trithiolanes. Eur J Org Chem. 2019;2019:1867–1875. doi: 10.1002/ejoc.201801708
   Web of Science ®Google Scholar
• Berger RG, editor. Flavours and fragrances. Chap. 12.3 and 13.6. Berlin: Springer-Verlag; 2007.
   Google Scholar
• Wratten SJ, Faulkner DJ. Cyclic polysulfides from the red alga Chondria californica. J Org Chem. 1976;41:2465–2467. doi: 10.1021/jo00876a025
   PubMed Web of Science ®Google Scholar
• Tjan SB, Haakmanc JC, Teunis CJ, et al. Synthesis of 3,5-dialkyl-1,2,4-trithiolanes. Assignment of configuration and conformational analysis by PMR. Tetrahedron. 1972;28:3489–3500 and references cited therein. doi: 10.1016/0040-4020(72)88110-9
   Web of Science ®Google Scholar
• Dorofeev IA, Shagun LG, Tokareva IA, et al. New synthesis of 1,2,4-trithiolane derivatives. Russ J Org Chem. 2008;44:1403–1405. doi: 10.1134/S1070428008090303
   Web of Science ®Google Scholar
• Boelens M, Van der Linde LM, De Valois PJ, et al. Organic sulfur compounds from fatty aldehydes, hydrogen sulfide, thiols, and ammonia as flavor constituents. J Agric Food Chem. 1974;22:1071–1076. doi: 10.1021/jf60196a036
   Web of Science ®Google Scholar
• Krafft C, Brennecke S, Weber B, et al. High-impact sulfur compounds: constitutional and configurational assignment of sulfur-containing heterocycles. Chem Biodivers. 2008;5:1204–1212. doi: 10.1002/cbdv.200890097
   PubMed Web of Science ®Google Scholar
• Ott F, Kindel G, Ley J, et al. Disubstituted tetrathianes as fragrances of flavourings. Int. Patent Pub. Num. WO 2006/027352 A1. 2006.
   Google Scholar
• Takikawa Y, Makabe T, Hirose N, et al. A novel method for the generation of thial S-sulfides from 2,4,6-trisubstituted 5,6-dihydro-1,3,5-dithiazines. Chem Lett. 1988;17:1517–1520. doi: 10.1246/cl.1988.1517
   Google Scholar
• Akhmetova VR, Dzhemileva UM, Tyumkina TY, et al. Regiodirected synthesis and stereochemistry of 2,4,8-trialkyl-3-thia-1,5-diazabicyclo[3.2.1]octanes and α,ω-bis(2,4,6-trialkyl-1,3,5-dithiazinane-5-yl)alkanes. J Heterocycl Chem. 2015;52:1037–1045. doi: 10.1002/jhet.2095
   Web of Science ®Google Scholar
• Okuma K, Shibata S, Shioji K, et al. A new simple synthesis of cis- and trans-3,5-di-tert-butyl-3,5-diaryl-1,2,4-trithiolanes from ketones and tetraphosphorus decasulfide. Chem Commun. 2000;2000(16):1535–1536. doi: 10.1039/b004013o
   Google Scholar
• Ishii A, Oshida H, Nakayama J. Structure elucidation of 6-t-butyl-6-phenylpentathiane monoxides by X-ray crystallography and DFT calculations. Bull Chem Soc Jpn. 2002;75:319–328. doi: 10.1246/bcsj.75.319
   Web of Science ®Google Scholar
• Mlostoń G, Celeda M, Linden A, et al. Synthesis of hetaryl-substituted 1,2,4-trithiolanes via a three-component reaction with dihetaryl thioketones, benzyl azide, and 2,2,4,4-tetramethyl-3-thioxocyclobutanone. J Sulfur Chem. 2016;37:14–22 and references cited therein. doi: 10.1080/17415993.2015.1082182
   Web of Science ®Google Scholar
• Mlostoń G, Heimgartner H. 103. Bildung von 1,2,4-trithiolanen in dreikomponenten-gemischen aus phenyl-azid, aromatischen thioketonen und 2,2,4,4-tetramethylcyclobutanthionen: eine schwefel-transfer-reaktion unter bildung von ‘thiocarbonylthiolaten’ ((alkylidensulfonio)thiolaten) als reaktive zwischenstufen. Helv Chim Acta. 1995;78:1298–1310. doi: 10.1002/hlca.19950780520
   Web of Science ®Google Scholar
• Mlostoń G, Romański J, Heimgartner H. Sulfur centered 1,3-dipoles. An efficient trapping of adamantanethione-S-sulfide generated in the reaction of adamantanethione with organic azides. Pol J Chem. 1996;70:437–445.
   Google Scholar
• Capperucci A, Degl'Innocenti A, Ricci A, et al. Silicon assisted synthesis of thiocarbonyl derivatives and reactivity of dienophilic thioaldehydes. J Org Chem. 1991;56:7323–7328. doi: 10.1021/jo00026a025
   Web of Science ®Google Scholar
• Degl’Innocenti A, Capperucci A, et al. Hexamethyldisilathiane based thionation of carbonyl compounds: a versatile approach to sulfur containing heterocycles. Synlett. 2005:1965–1983. doi: 10.1055/s-2005-872235
   Web of Science ®Google Scholar
• Tanini D, Angeli A, Capperucci A. Ionic liquids as an alternative reaction medium for HMDST based synthesis of thioaldehydes. Phosphorus Sulfur Silicon Relat Elem. 2016;191:156–158. doi: 10.1080/10426507.2015.1114487
   Web of Science ®Google Scholar
• Drabowicz J, Kielbasinski P, Lyzwa P, et al. Alkanesulfonic acids and acyclic derivatives. Sci Synth. 2007;39:17–122 and references cited therein.
   Google Scholar
• Delaney PA, Johnstone RAW. Solvent effects in the chlorination of tetrahydrothiophens with N-chlorosuccinimide. Tetrahedron. 1985;41:3845–3851. doi: 10.1016/S0040-4020(01)91405-X
   Web of Science ®Google Scholar
• Amosova SV, Gostevskaya VI, Gavrilova GM, et al. Divinyl sulfide. XI. 1-chlorovinyl- and 1-chloroethyl sulfides. Zh Org Khim. 1984;20:2521–2526. doi:10.1002/chin.198518147.
   Google Scholar
• Brandsma L, Arens JF. Chemistry of acetylenic ethers XLIX: Vinylthioethyne and some of its derivatives. Recl Trav Chim Pays Bas. 1961;80:237–240. doi: 10.1002/recl.19610800302
   Google Scholar
• Weissflog E, Schmidt M. Synthese von 2.4-dibrom-3-thiapentan. Phosphorus Sulfur. 1978;4:383–384. doi: 10.1080/03086647808069853
   Web of Science ®Google Scholar
• Konstantinova LS, Rakitin OA. Sulfur monochloride in organic synthesis. Russ Chem Rev. 2014;83:225–250 and references cited therein. doi: 10.1070/RC2014v083n03ABEH004354
   Web of Science ®Google Scholar
• Mloston G, Majchrzak A, Senning A, et al. Highly sulfurated heterocycles via dithiiranes and trithietanes as key intermediates. J Org Chem. 2002;67:5690–5695. doi: 10.1021/jo025766r
   PubMed Web of Science ®Google Scholar
• Sonavane SU, Chidambaram M, Almog J, et al. Rapid and efficient synthesis of symmetrical alkyl disulfides under phase transfer conditions. Tetrahedron Lett. 2007;48:6048–6050. doi: 10.1016/j.tetlet.2007.06.074
   Web of Science ®Google Scholar
• Adesoga K. Trithiolaniacin, a novel trithiolan from Petiveria alliacea. J Chem Soc Chem Commun. 1974;1974:906–907. doi: 10.1039/c39740000906
   Google Scholar