33.1.14.3 3,4-Dihydro-2H-thiopyrans and Derivatives (Update 2019)

Abstract

This chapter is an update to the earlier Science of Synthesis contribution (Section 33.1.14) describing methods for the synthesis of 3,4-dihydro-2H-thiopyrans and their derivatives. The most common routes to 2H-thiopyrans, 4H-thiopyrans, 3,4-dihydro-2H-thiopyrans, 4H-1-benzothiopyrans, 1H-2-benzothiopyrans, 2H-1-benzothiopyrans, and their derivatives are based on ring-closure reactions, ring transformation, elimination process, and the elaboration of substituents attached to the thiopyran ring.

Key words

2H-thiopyrans - 4H-thiopyrans - 3,4-dihydro-2H-thiopyrans - 4H-1-benzothiopyrans - 1H-2-benzothiopyrans - 2H-1-benzothiopyrans - sigmatropic rearrangement - base-induced cyclization - hetero-Diels–Alder reaction - domino Knoevenagel/hetero-Diels–Alder reaction - intramolecular cyclization - radical cyclization - hydrothiolation of alkynes

• 1 Ingall AH, In: Comprehensive Heterocyclic Chemistry II Katritzky AR, Rees CW, Scriven EFV. Pergamon New York 1996; 5. 501

• 2 Kuthan J, Sebek P, Böhm S. Adv. Heterocycl. Chem. 1994; 59: 179

• 3 Weissenfels M, Pulst M, Greif D. Sulfur Rep. 1993; 15: 161

• 4 Ingall AH, In: Comprehensive Heterocyclic Chemistry Katritzky AR, Rees. C. W. Eds. Pergamon New York 1984; 3. 885

• 5 Majumdar KC, Pal AK. J. Sulfur Chem. 2009; 30: 481

• 6 Majumdar KC, Pal AK. Can. J. Chem. 2008; 86: 72

• 7 Majumdar KC, Islam R, Alam S. Synth. Commun. 2008; 38: 754

• 8 Hatial I, Das J, Ghosh AK, Basak A. Eur. J. Org. Chem. 2015; 6017

• 9 Hossain MS, Schwan AL. Org. Lett. 2011; 13: 5330

• 10 Ho LU, Shkoor MGh, Hossain MS, Deen MC, Soldatov DV, Schwan AL. J. Sulfur Chem. 2013; 34: 79

• 11 Shyshkina OO, Tkachuk TM, Volovnenko TA, Volovenko YM, Zubatyuk RI, Medviediev VV, Shishkin OV. Tetrahedron Lett. 2012; 53: 4296

• 12 Lozynskyi A, Zimenkovsky B, Lesyk R. Sci. Pharm. 2014; 82: 723

• 13 Lozynskyi A, Zimenkovsky B, Karkhut A, Polovkovych S, Gzella AK, Lesyk R. Tetrahedron Lett. 2016; 57: 3318

• 14 Kaminskyy D, Vasylenko O, Atamanyuk D, Gzella A, Lesyk R. Synlett 2011; 1385

• 15 Zelisko N, Atamanyuk D, Ostapiuk Y, Bryhas A, Matiychuk V, Gzella A, Lesyk R. Tetrahedron 2015; 71: 9501

• 16 Zelisko N, Atamanyuk D, Vasylenko O, Grellier P, Lesyk R. Bioorg. Med. Chem. Lett. 2012; 22: 7071

• 17 Metwally NH, Badawy MA, Okpy DS. Chem. Pharm. Bull. 2015; 63: 495

• 18 Metwally NH. Heterocycles 2008; 75: 319

• 19 Lozynskyi A, Zimenkovsky B, Nektegayev I, Lesyk R. Heterocycl. Commun. 2015; 21: 55

• 20 Metwally NH. J. Sulfur Chem. 2014; 35: 528

• 21 Atamanyuk D, Zimenkovsky B, Lesyk R. J. Sulfur Chem. 2008; 29: 151

• 22 Badawy MA, Metwally NH, Okpy DS. J. Sulfur Chem. 2015; 36: 511

• 23 Polovkovych SV, Karkhut AI, Marintsova NG, Lesyk RB, Zimenkovsky BS, Novikov VP. J. Heterocycl. Chem. 2013; 50: 1419

• 24 Metwally NH. Phosphorus, Sulfur Silicon Relat. Elem. 2008; 183: 2073

• 25 Zayeda SE, El-Maghrabya AM, Hassan EA. Phosphorus, Sulfur Silicon Relat. Elem. 2014; 189: 1682

• 26 Lozynskyi A, Golota S, Zimenkovsky B, Atamanyuk D, Gzella A, Lesyk R. Phosphorus, Sulfur Silicon Relat. Elem. 2016; 191: 1245

• 27 Erol S, Dogan I. Tetrahedron 2013; 69: 1337

• 28 Zelisko N, Atamanyuk D, Vasylenko O, Bryhas A, Matiychuk V, Gzella A, Lesyk R. Tetrahedron 2014; 70: 720

• 29 Pokhodylo NT, Obushak MD, Matiychuk VS. Chem. Heterocycl. Compd. (Engl. Transl.) 2011; 47: 1053

• 30 Hegab MI, Elmalah TAG, Gad FA. Phosphorus, Sulfur Silicon Relat. Elem. 2009; 184: 1665

• 31 Mlostoń G, Grzelak P, Mikina M, Linden A, Heimgartner H. Beilstein J. Org. Chem. 2015; 11: 576

• 32 Matiychuk VS, Lesyk RB, Obushak MD, Gzella A, Atamanyuk DV, Ostapiuk YV, Kryshchyshyn AP. Tetrahedron Lett. 2008; 49: 4648

• 33 Pokhodylo NT, Savka RD, Obushak MD. Chem. Heterocycl. Compd. (Engl. Transl.) 2014; 50: 544

• 34 Saito T, Kobayashi S, Otani T, Iwanami H, Soda T. Heterocycles 2008; 76: 227

• 35 Siry SA, Timoshenko VM, Vlasenko YG, Baranova GV, Zagorodnya SD, Nesterova NV. Chem. Heterocycl. Compd. (Engl. Transl.) 2014; 50: 467

• 36 Parmar BD, Sutariya TR, Brahmbhatt GC, Parmar NJ, Kant R, Gupta VK, Murumkar PR, Sharma MK, Yadav MR. Mol. Diversity 2016; 20: 639

• 37 Parmar NJ, Parmar BD, Sutariya TR, Kant R, Gupta VK. Tetrahedron Lett. 2014; 55: 6060

• 38 Zhang Y, Wang S, Wu S, Zhu S, Dong G, Miao Z, Yao J, Zhang W, Sheng C, Wang W. ACS Comb. Sci. 2013; 15: 298

• 39 Buchotte M, Muzard M, Plantier-Royon R. Eur. J. Org. Chem. 2008; 3529

• 40 Buchotte M, Bello C, Vogel P, Floquet N, Muzard M, Plantier-Royon R. Tetrahedron: Asymmetry 2009; 20: 2038

• 41 Kvasnica M, Rudovska I, Cisarova I, Sarek J. Tetrahedron 2008; 64: 3736

• 42 Oh K, Kim H, Cardelli F, Bwititi T, Martynow AM. J. Org. Chem. 2008; 73: 2432

• 43 Zhao Q, Li L, Fang Y, Sun D, Li C. J. Org. Chem. 2009; 74: 459

• 44 Pieroni M, Dimovska M, Brincat JP, Sabatini S, Carosati E, Massari S, Kaatz GW, Fravolini A. J. Med. Chem. 2010; 53: 4466

• 45 Abd El-Salam OI, Alsayed AS, Ali KA, Abd Elwahab AA, Amr AE.-GE, Awad HM. Molecules 2015; 20: 20 434

• 46 Grellepois F, Timoshenko VM, Rusanov EB, Shermolovich YG, Portella C. J. Fluorine Chem. 2010; 131: 937

• 47 Wang S, Zhang Y, Dong G, Wu S, Zhu S, Miao Z, Yao J, Li H, Li J, Zhang W, Sheng C, Wang W. Org. Lett. 2013; 15: 5570

• 48 Silveira CC, Rinaldi F, Bassaco MM, Kaufman TS. Tetrahedron Lett. 2008; 49: 5782

• 49 Koley S, Chowdhury S, Chanda T, Ramulu BJ, Singh MS. Tetrahedron 2013; 69: 8013

• 50 Li D, Xu X, Liu Q, Dong S. Synthesis 2008; 1895

• 51 Du D, Xu Q, Li X.-G, Shi M. Chem.–Eur. J. 2016; 22: 4733

• 52 Wen L.-R, Wang L.-J, Li M. Chin. J. Struct. Chem. 2011; 30: 867

• 53 Yamamoto T, Aoki K, Sugiyama A, Doi H, Kodama T, Shimizu Y, Kanai M. Chem.–Asian J. 2015; 10: 1071

• 54 Corce V, McSweeney L, Malone A, Scanlan EM. Chem. Commun. (Cambridge) 2015; 51: 8672

• 55 Cui Y, Floreancig PE. Org. Lett. 2012; 14: 1720

• 56 Feng J, Lv M, Lu G, Cai C. Eur. J. Org. Chem. 2014; 5312

• 57 Schneider CC, Bortolatto C, Back DF, Menezes PH, Zeni G. Synthesis 2011; 413

• 58 Minami Y, Kuniyasu H, Kambe N. Org. Lett. 2008; 10: 2469

• 59 Shi S, Sun L.-L, Liao Z.-Y, Zhang X.-G. Synthesis 2012; 44: 966

• 60 Zhou H, Xie Y, Ren L, Wang K. Adv. Synth. Catal. 2009; 351: 1289

• 61 Majumdar KC, Islam R. Synth. Commun. 2008; 38: 4053

• 62 Manna SK, Parai MK, Panda G. Tetrahedron Lett. 2011; 52: 5951

• 63 Shen C, Spannenberg A, Wu X.-F. Angew. Chem. Int. Ed. 2016; 55: 5067

• 64 Willy B, Frank W, Müller TJJ. Org. Biomol. Chem. 2010; 8: 90

• 65 Willy B, Müller TJJ. Synlett 2009; 1255

• 66 Palani T, Park K, Song KH, Lee S. Adv. Synth. Catal. 2013; 355: 1160

• 67 Bouisseau A, Glancy J, Willis MC. Org. Lett. 2016; 18: 5676

• 68 Volpe R, Aurelio L, Gillin MG, Krenske EH, Flynn BL. Chem.–Eur. J. 2015; 21: 10 191

• 69 Lee JI. Bull. Korean Chem. Soc. 2012; 33: 1375

• 70 Fuchs FC, Eller GA, Holzer W. Molecules 2009; 14: 3814

• 71 Yang X, Li S, Liu H, Jiang Y, Fu H. RSC Adv. 2012; 2: 6549

• 72 Lee JI. Bull. Korean Chem. Soc. 2009; 30: 710

• 73 Lee JI, Kim MJ. Bull. Korean Chem. Soc. 2011; 32: 1383

• 74 Szamosvári D, Reichle VF, Jureschi M, Böttcher T. Chem. Commun. (Cambridge) 2016; 52: 13 440

• 75 Choi EJ, Lee JI, Kim G.-H. Int. J. Mol. Med. 2012; 29: 252

• 76 Kumaraswamy G, Raghu N, Kumar RS. Org. Prep. Proced. Int. 2014; 46: 435

• 77 Mabe PJC, Knick SL, Shuler WG, Carlisle SS, Smith EA, Puciaty AJ, McFadden TMC, Potter C, Metz CR, Beam CF, Pennington WT, VanDerveer DG, McMillan CD. Ind. Eng. Chem. Res. 2015; 54: 7207

• 78 Kikionis S, McKee V, Markopoulos J, Igglessi-Markopoulou O. Tetrahedron 2008; 64: 5454

• 79 Metz CR, Knight JD, Pastine SJ, Pennington WT, Beam CF. J. Chem. Crystallogr. 2010; 40: 536

• 80 Vijay TAJ, Nandeesh KN, Raghavendra GM, Rangappa KS, Mantelingu K. Tetrahedron Lett. 2013; 54: 6533

• 81 Zhang Y, Tanimoto H, Nishiyama Y, Morimoto T, Kakiuchi K. Synlett 2012; 23: 367

• 82 Sabatini S, Gosetto F, Manfroni G, Tabarrini O, Kaatz GW, Patel D, Cecchetti V. J. Med. Chem. 2011; 54: 5722

• 83 Kitani S, Sugawara K, Tsutsumi K, Morimoto T, Kakiuchi K. Chem. Commun. (Cambridge) 2008; 2103

• 84 Huang C.-N, Chuang R.-R, Kuo P.-Y, Yang D.-Y. Synlett 2008; 1825

• 85 Wen L.-R, Ji C, Li M, Xie H.-Y. Tetrahedron 2009; 65: 1287

• 86 Wen L.-R, Sun J.-H, Li M, Sun E.-T, Zhang S.-S. J. Org. Chem. 2008; 73: 1852

• 87 Kanani MB, Patel MP. RSC Adv. 2014; 4: 28 798

• 88 Gu Z.-Y, Cao J.-J, Wang S.-Y, Ji S.-J. Chem. Sci. 2016; 7: 4067

• 89 Kobayashi K, Kobayashi A, Ezaki K. Heterocycles 2012; 85: 1997

• 90 Tabarrini O, Massari S, Daelemans D, Meschini F, Manfroni G, Bottega L, Gatto B, Palumbo M, Pannecouque C, Cecchetti V. ChemMedChem 2010; 5: 1880

• 91 Varedian M, Langer V, Bergquist J, Gogoll A. Tetrahedron Lett. 2008; 49: 6033

• 92 Mandal TK, Pal R, Mondal R, Dey SP, Mallik AK. J. Chem. 2013; 392 128

• 93 Yokoyama S, Hirose T, Matsuda K. Langmuir 2015; 31: 6404

• 94 Hirose T, Inoue Y, Hasegawa J.-Y, Higashiguchi K, Matsuda K. J. Phys. Chem. A 2014; 118: 1084

• 95 Frath D, Sakano T, Imaizumi Y, Yokoyama S, Hirose T, Matsuda K. Chem.–Eur. J. 2015; 21: 11 350

• 96 Huang H, Li J, Lescop C, Duan Z. Org. Lett. 2011; 13: 5252

• 97 Li J, Huang H, Liang W, Gao Q, Duan Z. Org. Lett. 2013; 15: 282

• 98 Inami T, Kurahashi T, Matsubara S. Org. Lett. 2014; 16: 5660

• 99 Inami T, Baba T, Kurahashi T, Matsubara S. Org. Lett. 2011; 13: 1912

• 100 Palanisamy P, Jenniefer SJ, Muthiah PT, Kumaresan S. RSC Adv. 2013; 3: 19 300

• 101 Mal K, Kaur A, Haque F, Das I. J. Org. Chem. 2015; 80: 6411

• 102 Duan Z, Wie Z, Xu W, Zhu D. Tetrahedron Lett. 2009; 50: 2597

• 103 Song Y.-L, Wu F, Zhang C.-C, Liang G.-C, Zhou G, Yu J.-J. Bioorg. Med. Chem. Lett. 2015; 25: 259

• 104 Yuasa H, Tanetani Y, Miyazaki T, Izumi M, Hashimoto H. Lett. Org. Chem. 2008; 5: 262

• 105 Yuasa H, Tsuruta O, Izumi T, Takahara T, Izumi M, Hashimoto H. Chem. Lett. 2008; 37: 1288

• 106 Goyard D, Baron M, Skourti PV, Chajistamatiou AS, Docsa T, Gergely P, Chrysina ED, Praly J.-P, Vidal S. Carbohydr. Res. 2012; 364: 28

• 107 Aitken RA, Hauduc C, Hossain MS, McHale E, Schwan AL, Slawin AMZ, Stewart CA. Aust. J. Chem. 2014; 67: 1288

• 108 Sangeetha S, Muthupandi P, Sekar G. Org. Lett. 2015; 17: 6006

• 109 Iaroshenko VO, Mkrtchyan S, Gevorgyan A, Vilches-Herrera M, Sevenard DV, Villinger A, Ghochikyan TV, Saghiyan A, Sosnovskikh VY, Langer P. Tetrahedron 2012; 68: 2532

• 110 Sevenard DV, Barabanov MA, Sosnovskikh VY. Russ. Chem. Bull. 2010; 59: 297

• 111 Siryi SA, Timoshenko VM, Vlasenko YG, Rusanov EB, Shermolovich YG. Chem. Heterocycl. Compd. (Engl. Transl.) 2015; 51: 630

• 112 Siry SA, Timoshenko VM. Tetrahedron Lett. 2011; 52: 6260

• 113 Klier LM, Bresser T, Nigst TA, Karaghiosoff K, Knochel P. J. Am. Chem. Soc. 2012; 134: 13 584

• 114 Hammann JM, Haas D, Knochel P. Angew. Chem. Int. Ed. 2015; 54: 4478

• 115 Narayan R, Antonchick AP. Chem.–Eur. J. 2014; 20: 4568

• 116 Deagostino A, Larini P, Occhiato EG, Pizzuto L, Prandi C, Venturello P. J. Org. Chem. 2008; 73: 1941

• 117 Bhattacharya C, Bonfante P, Deagostino A, Kapulnik Y, Larini P, Occhiato EG, Prandi C, Venturello P. Org. Biomol. Chem. 2009; 7: 3413