Recent Advances in Sulfur-Containing Heterocycle Formation via Direct C–H Sulfuration with Elemental Sulfur

Saiwen Liu; Guo-Jun Deng; Huawen Huang

doi:10.1055/s-0040-1707217

Synlett, Table of Contents

Synlett 2021; 32(02): 142-158
DOI: 10.1055/s-0040-1707217

cluster

Recent Advances in Sulfur-Containing Heterocycle Formation via Direct C–H Sulfuration with Elemental Sulfur

Saiwen Liu

^aCollege of Materials and Chemical Engineering, Hunan City University, Yiyang 413000, P. R. of China

^bKey Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. of China Email: gjdeng@xtu.edu.cn Email: hwhuang@xtu.edu.cn

,

Guo-Jun Deng∗

^bKey Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. of China Email: gjdeng@xtu.edu.cn Email: hwhuang@xtu.edu.cn

,

Huawen Huang∗

^bKey Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. of China Email: gjdeng@xtu.edu.cn Email: hwhuang@xtu.edu.cn

› Author Affiliations

Abstract

All articles of this category

Published as part of the Cluster Modern Heterocycle Synthesis and Functionalization

Abstract

The synthesis of sulfur heterocycles via the construction of C–S bonds has received considerable attention due to their biological value and extensive pharmaceutical application. While diverse sulfurating agents have been developed over the past few decades, in this regard, elemental sulfur, with advantages of low toxicity, odorless nature and chemical stability, has great potential for the construction of diverse sulfur heterocycles through its direct incorporation into the target molecules in a concise way. Direct functionalization of inert C–H bonds can shorten the number of reaction steps and minimize the amount of waste formed. Hence, heteroannulations via direct C–H sulfuration is considered to be an attractive strategy for the synthesis of sulfur heterocycles. In the last few years, a vast array of concise systems have been reported for the synthesis of some valuable sulfur heterocycles such as thiophenes, thienoindoles, thienothiazoles, thiazoles, benzothiazoles, and thiadiazoles through direct C–H sulfuration/annulations with elemental sulfur. These are discussed in detail in this review.

1 Introduction

2 Thiophenes

3 Thienoindoles

4 Thienothiazoles

5 Other Fused Thiophenes

6 Thiazoles

7 Benzothiazoles

8 Thiadiazoles

9 Others

10 Summary and Outlook

Key words

sulfur heterocycles - C–H sulfuration - elemental sulfur - concise synthesis - multicomponent reactions

Full Text

References

References and Notes

1a Domling A, Beck B, Eichelberger U, Sakamuri S, Menon S, Chen QZ, Lu Y, Wessjohann LA. Angew. Chem. Int. Ed. 2006; 45: 7235
1b Tomasic T, Katsamakas S, Hodnik Z, Ilas J, Brvar M, Solmajer T, Montalvao S, Tammela P, Banjanac M, Ergovic G, Anderluh M, Peterlin Masic L, Kikelj D. J. Med. Chem. 2015; 58: 5501
1c Wojtas KP, Riedrich M, Lu JY, Winter P, Winkler T, Walter S, Arndt HD. Angew. Chem. Int. Ed. 2016; 55: 9772
1d Zhao J, Jiang X. Chin. Chem. Lett. 2018; 29: 1079
1e Feng MH, Tang BQ, Liang SH, Jiang XF. Curr. Top. Med. Chem. 2016; 16: 1200
1f Wang NZ, Saidhareddy P, Jiang XF. Nat. Prod. Rep. 2020; 37: 246

2 Kanbe K, Naganawa H, Nakamura KT, Okami Y, Takeuchi T. Biosci., Biotechnol., Biochem. 1993; 57: 632
3 Schentag J.-J, Smith LL, Swanson DJ, DeAngelis C, Fracasso JE, Vari A, Vance JW. Am. J. Med. 1984; 77: 43
4 Tishler RB, Lamppu DM, Park S, Brendan DP. Cancer Res. 1995; 55: 6021

5a Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
5b Lee CF, Liu YC, Badsara SS. Chem. Asian J. 2014; 9: 706
5c Liu H, Jiang X. Chem. Asian J. 2013; 8: 2546
5d Shen C, Zhang P, Sun Q, Bai S, Hor TS, Liu X. Chem. Soc. Rev. 2015; 44: 291
5e Qiao Z, Jiang X. Org. Biomol. Chem. 2017; 15: 1942
5f Liu J, Zheng L. Adv. Synth. Catal. 2019; 361: 1710
5g Wang M, Li YP, Jiang XF. Aldrichimica Acta 2020; 53: 19

6a Nguyen TB. Adv. Synth. Catal. 2017; 359: 1066
6b Nguyen TB. Adv. Synth. Catal. 2020;
6c Fedenok LG, Fedotov KY, Pritchina EA, Polyakov NE. Tetrahedron Lett. 2016; 57: 1273
6d Huang MQ, Li TJ, Liu JQ, Shatskiy A, Kärkäs MD, Wang XS. Org. Lett. 2020; 22: 3454
6e Petrov V, Dooley RJ, Marchione AA, Diaz EL, Clem BS. J. Fluorine Chem. 2019; 225: 1
6f Ying J, Wang H, Qi XX, Peng JB, Wu XF. Eur. J. Org. Chem. 2018; 688
6g Sakai N, Horikawa S, Ogiwara Y. Synthesis 2018; 50: 565
6h Petrov V, Marchione AA, Dooley R. Chem. Commun. 2018; 54: 9298
6i Ibragimov AG, Makhmudiyarov GA, Shaibakova MG, Khalilov LM, Dzhemilev UM. Russ. J. Org. Chem. 2019; 55: 1890

7a Liu W, Chen C, Liu H. Adv. Synth. Catal. 2015; 357: 4050
7b Zhang G, Yi H, Chen H, Bian C, Liu C, Lei A. Org. Lett. 2014; 16: 6156

8a Jiang P, Che X, Liao Y, Huang H, Deng G.-J. RSC Adv. 2016; 6: 41751
8b Nguyen LA, Ngo QA, Retailleau P, Nguyen TB. Green Chem. 2017; 19: 4289
8c Nguyen TB, Ermolenko L, Retailleau P, Al-Mourabit A. Angew. Chem. Int. Ed. 2014; 53: 13808
8d Siva ReddyA, Kumara SwamyK. C. Org. Lett. 2015; 17: 2996
8e Xie H, Li G, Zhang F, Xiao F, Deng G.-J. Green Chem. 2018; 20: 827
8f Yang Z, Hu R, Li X, Wang X, Gu R, Han S. Tetrahedron Lett. 2017; 58: 2366
8g Wang M, Fan QL, Jiang XF. Org. Lett. 2016; 18: 5756

9a Chen FJ, Liao G, Li X, Wu J, Shi BF. Org. Lett. 2014; 16: 5644
9b Chen J, Li G, Xie Y, Liao Y, Xiao F, Deng GJ. Org. Lett. 2015; 17: 5870
9c Xie H, Cai J, Wang Z, Huang H, Deng GJ. Org. Lett. 2016; 18: 2196
9d Chen S, Wang M, Jiang X. Acta Phys.-Chim. Sin. 2019; 35: 954

10a Colletto C, Islam S, Julia-Hernandez F, Larrosa I. J. Am. Chem. Soc. 2016; 138: 1677
10b Sudo Y, Yamaguchi E, Itoh A. Org. Lett. 2017; 19: 1610
10c Tang DT, Collins KD, Glorius F. J. Am. Chem. Soc. 2013; 135: 7450
10d Zhang Y, Zhao H, Zhang M, Su W. Angew. Chem. Int. Ed. 2015; 54: 3817

11a Bharathiraja G, Sathishkannan G, Punniyamurthy T. J. Org. Chem. 2016; 81: 2670
11b Jullien H, Quiclet-Sire B, Tetart T, Zard SZ. Org. Lett. 2014; 16: 302
11c Pigulski B, Mecik P, Cichos J, Szafert S. J. Org. Chem. 2017; 82: 1487
11d Talbi I, Alayrac C, Lohier JF, Touil S, Witulski B. Org. Lett. 2016; 18: 2656

12a Gewald K. Chem. Ber. 1965; 98: 3571
12b Gewald K, Schinke E. Chem. Ber. 1966; 99: 2712
12c Gewald K, Schinke E, Böttcher H. Chem. Ber. 1966; 99: 94

13 Shao W, Kaldas SJ, Yudin AK. Chem. Sci. 2017; 8: 4431
14 Thomas J, Jana S, Sonawane M, Fiey B, Balzarini J, Liekens S, Dehaen W. Org. Biomol. Chem. 2017; 15: 3892
15 Kavitha K, Srikrishna D, Dubey PK, Aparna P. J. Sulfur Chem. 2019; 40: 195
16 Nguyen TT. T, Le VA, Retailleau P, Nguyen TB. Adv. Synth. Catal. 2019; 362: 160
17 Nguyen TB, Pasturaud K, Ermolenko L, Al-Mourabit A. Org. Lett. 2015; 17: 2562
18 Nguyen TB, Retailleau P. Green Chem. 2018; 20: 387
19 Nguyen TB, Retailleau P. Org. Lett. 2017; 19: 4858
20 Nguyen TB, Retailleau P. Org. Lett. 2018; 20: 186
21 Wang Z, Qu Z, Xiao F, Huang H, Deng G.-J. Adv. Synth. Catal. 2018; 360: 796

22a Adib M, Rajai-Daryasarei S, Pashazadeh R, Jahani M, Amanlou M. Synlett 2018; 29: 1583
22b Adib M, Rajai-Daryasarei S, Pashazadeh R, Jahani M, Yazzaf R, Amanlou M. Eur. J. Org. Chem. 2018; 3001

23 Sakai S, Sato K, Yoshida K. Tetrahedron Lett. 2020; 61: 151476
24 Fukutani T, Hirano K, Satoh T, Miura M. J. Org. Chem. 2011; 76: 2867
25 Moon S, Kato M, Nishii Y, Miura M. Adv. Synth. Catal. 2020; 362: 1669
26 Meng L, Fujikawa T, Kuwayama M, Segawa Y, Itami K. J. Am. Chem. Soc. 2016; 138: 10351
27 Shoji T, Miura K, Ohta A, Sekiguchi R, Ito S, Endo Y, Nagahata T, Mori S, Okujima T. Org. Chem. Front. 2019; 6: 2801
28 Wu J, He D, Wang Y, Su F, Guo Z, Lin J, Zhang HJ. Org. Lett. 2018; 20: 6117
29 Su F, Chen S, Mo X, Wu K, Wu J, Lin W, Lin Z, Lin J, Zhang H.-J, Wen T.-B. Chem. Sci. 2020; 11: 1503
30 Chen L, Xia P, Du T, Deng Y, Xiao Y. Org. Lett. 2019; 21: 5529
31 Pedras MS, Suchy M. Bioorg. Med. Chem. 2006; 14: 714
32 Baert F, Cabanetos C, Allain M, Silvestre V, Leriche P, Blanchard P. Org. Lett. 2016; 18: 1582
33 Liao Y, Peng Y, Qi H, Deng GJ, Gong H, Li CJ. Chem. Commun. 2015; 51: 1031
34 Li B, Ni P, Huang H, Xiao F, Deng G.-J. Adv. Synth. Catal. 2017; 359: 4300

35a Chen S, Li Y, Ni P, Huang H, Deng GJ. Org. Lett. 2016; 18: 5384
35b Chen S, Li Y, Ni P, Yang B, Huang H, Deng GJ. J. Org. Chem. 2017; 82: 2935
35c Chen S, Wang L, Zhang J, Hao Z, Huang H, Deng GJ. J. Org. Chem. 2017; 82: 11182

36 Ni P, Li B, Huang H, Xiao F, Deng G.-J. Green Chem. 2017; 19: 5553
37 Nguyen TT, Tran PH. RSC Adv. 2020; 10: 9663
38 Zhang H.-L, Wen F, Sheng W.-B, Yin P, Zhang C.-T, Peng C.-Y, Peng D.-M, Liao D.-F, Fu R.-G. Tetrahedron Lett. 2019; 60: 80
39 Lu C, Huang H, Tuo X, Jiang P, Zhang F, Deng G.-J. Org. Chem. Front. 2019; 6: 2738
40 Liu Z, Gao R, Lou J, He Y, Yu Z. Adv. Synth. Catal. 2018; 360: 3097
41 Liu J, Zhang Y, Yue Y, Wang Z, Shao H, Zhuo K, Lv Q, Zhang Z. J. Org. Chem. 2019; 84: 12946
42 Huang H, Xu Z, Ji X, Li B, Deng GJ. Org. Lett. 2018; 20: 4917
43 Huang H, Wang Q, Xu Z, Deng GJ. Adv. Synth. Catal. 2018; 361: 591
44 Huang H, Qu Z, Ji X, Deng G.-J. Org. Chem. Front. 2019; 6: 1146

45a Tang X, Yang J, Zhu Z, Zheng M, Wu W, Jiang H. J. Org. Chem. 2016; 81: 11461
45b Zhu Z, Tang X, Cen J, Li J, Wu W, Jiang H. Chem. Commun. 2018; 54: 3767

46 Zhou P, Huang Y, Wu W, Yu W, Li J, Zhu Z, Jiang H. Org. Biomol. Chem. 2019; 17: 3424
47 Pham PH, Nguyen KX, Pham HT. B, Tran TT, Nguyen TT, Phan NT. S. RSC Adv. 2020; 10: 11024
48 Zhang W, Tao SQ, Ge HB, Li Q, Ai ZK, Li XX, Zhang BB, Sun FX, Xu XQ, Du YF. Org. Lett. 2020; 22: 448
49 Pham PH, Nguyen KX, Pham HT. B, Nguyen TT, Phan NT. S. Org. Lett. 2019; 21: 8795
50 Zhou P, Huang Y, Wu W, Zhou J, Yu W, Jiang H. Org. Lett. 2019; 21: 9976
51 Pham PH, Nguyen KX, Nguyen NP, Pham HT. B, Nguyen TT, Phan NT. S. Asian J. Org. Chem. 2020; 9: 622
52 Shi T, Zerio CJ, Sivinski J, Ambrose AJ, Moore KT, Buckley T, Kaneko L, Zhang M, Zhang DD, Chapman E. Eur. J. Org. Chem. 2019; 3269

53a Ravi C, Adimurthy S. Chem. Rec. 2017; 17: 1019
53b Ravi C, Joshi A, Adimurthy S. Eur. J. Org. Chem. 2017; 3646

54 Semwal R, Ravi C, Saxena S, Adimurthy S. J. Org. Chem. 2019; 84: 14151
55 Xu Z, Deng GJ, Zhang F, Chen H, Huang H. Org. Lett. 2019; 21: 8630
56 Teja C, Nawaz Khan FR. Org. Lett. 2020; 22: 1726
57 Zhang P, Chen W, Liu M, Wu H. Org. Lett. 2019; 21: 9326
58 Wilson ZE, Fenner S, Ley SV. Angew. Chem. Int. Ed. 2015; 54: 1284

59a Hantzsch A. Ber. Dtsch. Chem. Ges. 1888; 21: 942
59b Kumar SV, Parameshwarappa G, Ila H. J. Org. Chem. 2013; 78: 7362

60 Wu M, Jiang Y, An Z, Qi Z, Yan R. Adv. Synth. Catal. 2018; 360: 4236
61 Wang X, Qiu X, Wei J, Liu J, Song S, Wang W, Jiao N. Org. Lett. 2018; 20: 2632
62 Okesola BO, Mata A. Chem. Soc. Rev. 2018; 47: 3721
63 Jiang J, Huang H, Deng G.-J. Green Chem. 2019; 21: 986
64 Fu RG, Wang Y, Xia F, Zhang HL, Sun Y, Yang DW, Wang YW, Yin P. J. Org. Chem. 2019; 84: 12237
65 Ni P, Tan J, Li R, Huang H, Zhang F, Deng G.-J. RSC Adv. 2020; 10: 3931
66 Jonaghani MZ, Zali-Boeini H, Taheri R, Rudbari HA, Askari B. RSC Adv. 2016; 6: 34940
67 Li G, Xie H, Chen J, Guo Y, Deng G.-J. Green Chem. 2017; 19: 4043
68 Che X, Jiang J, Xiao F, Huang H, Deng GJ. Org. Lett. 2017; 19: 4576
69 Singh M, Awasthi P, Singh V. Eur. J. Org. Chem. 2020; 1023

70a Dang P, Zheng Z, Liang Y. J. Org. Chem. 2017; 82: 2263
70b Zhang X, Zeng W, Yang Y, Huang H, Liang Y. Org. Lett. 2014; 16: 876

71 Zhu X, Yang Y, Xiao G, Song J, Liang Y, Deng G. Chem. Commun. 2017; 53: 11917
72 Jiang J, Li G, Zhang F, Xie H, Deng G.-J. Adv. Synth. Catal. 2018; 360: 1622
73 Liu Y, Yuan X, Guo X, Zhang X, Chen B. Tetrahedron 2018; 74: 6057
74 Zhang J, Zhao X, Liu P, Sun P. J. Org. Chem. 2019; 84: 12596

75a Wang HM, Cao XX, Xiao FH, Liu SW, Deng GJ. Org. Lett. 2013; 15: 4900
75b Wu M, Hu X, Liu J, Liao Y, Deng GJ. Org. Lett. 2012; 14: 2722

76 Xing Q, Ma Y, Xie H, Xiao F, Zhang F, Deng GJ. J. Org. Chem. 2019; 84: 1238

77a Chen J, Chang D, Xiao F, Deng G.-j. Prog. Chem. 2018; 30: 564
77b Girard SA, Huang H, Zhou F, Deng G.-J, Li C.-J. Org. Chem. Front. 2015; 2: 279

78 Xu Z, Huang H, Chen H, Deng G.-J. Org. Chem. Front. 2019; 6: 3060
79 Wang Z, Xie H, Xiao F, Guo Y, Huang H, Deng G.-J. Eur. J. Org. Chem. 2017; 1604

80a Chen J, Jiang Y, Yu JT, Cheng J. J. Org. Chem. 2016; 81: 271
80b Zhou Z, Liu Y, Chen J, Yao E, Cheng J. Org. Lett. 2016; 18: 5268

81 Zhou Z, Liu M, Sun S, Yao E, Liu S, Wu Z, Yu J.-T, Jiang Y, Cheng J. Tetrahedron Lett. 2017; 58: 2571
82 Yang Z, Liang Y, Li A, Liu K, Li L, Yang T, Zhou C. J. Org. Chem. 2019; 84: 16262
83 Ishikawa T, Kimura M, Kumoi T, Iida H. ACS Catal. 2017; 7: 4986
84 Li W, He J, Liu P, Zhang J, Dai B. ChemistrySelect 2019; 4: 10587
85 Mo SK, Teng QH, Pan YM, Tang HT. Adv. Synth. Catal. 2019; 361: 1756
86 Nguyen TB, Retailleau P. Org. Lett. 2017; 19: 3879
87 Guo JR, Gong JF, Song MP. Org. Biomol. Chem. 2019; 17: 5029
88 Zhang J, Song C, Sheng L, Liu P, Sun P. J. Org. Chem. 2019; 84: 2191
89 Nguyen TB, Retailleau P. Org. Lett. 2019; 21: 279
90 Jiang J, Tuo X, Fu Z, Huang H, Deng GJ. Org. Biomol. Chem. 2020; 18: 3234
91 Chen Q, Xie R, Jia H, Sun J, Lu G, Jiang H, Zhang M. J. Org. Chem. 2020; 85: 5629