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Synlett 2019; 30(18): 2041-2050
DOI: 10.1055/s-0037-1611905
DOI: 10.1055/s-0037-1611905
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Recent Advances in the Synthesis of Thiadiazoles
We thank the National Natural Science Foundation of China (No. 21572025, 21602019, 21672028), “Innovation & Entrepreneurship Talents” Introduction Plan of Jiangsu Province, Natural Science Foundation of Jiangsu Province (BK20171193), Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology (BM2012110), and the Advanced Catalysis and Green Manufacturing Collaborative Innovation Center for financial support.Further Information
Publication History
Received: 03 July 2019
Accepted after revision: 16 July 2019
Publication Date:
05 September 2019 (online)
Abstract
Thiadiazole moieties are present in many natural products and pharmaceutical compounds that possess a broad spectrum of biological activities, serving as antidepressant, anxiolytic, antimicrobial, antitubercular, antiinflammatory, antidiabetic, anticancer, antihypertensive, or antifungal drugs. Many excellent methods have been reported for accessing such frameworks. In this review, we summarize advances made within the past ten years in the synthesis of various types of thiadiazole.
1 Introduction
2 Synthesis of Thiadiazoles
2.1 Synthesis of 1,2,3-Thiadiazoles
2.1.1 Synthesis of 1,2,3-Thiadiazoles from Diazo/Azide Compounds
2.1.2 Synthesis of 1,2,3-Thiadiazoles from Sulfonyl Hydrazines or N-Tosylhydrazones
2.2 Synthesis of 1,2,4-Thiadiazoles
2.2.1 Synthesis of 1,2,4-Thiadiazoles from Thioamides or their Derivatives
2.2.2 Synthesis of 1,2,4-Thiadiazoles from Amidines or 2-Aminopyridines
2.3 Synthesis of 1,3,4-Thiadiazoles
2.4 Synthesis of 1,2,5-Thiadiazoles
3 Conclusion
-
References
- 1a Vadivelu A, Gopal V, Reddy CU. M, Evanjelene VK. J. Chem. Pharm. Res. 2014; 6: 855
- 1b Haider S, Alam MS, Hamid H. Eur. J. Med. Chem. 2015; 92: 156
- 1c Hu Y, Li C.-Y, Wang X.-M, Yang Y.-H, Zhu H.-L. Chem. Rev. 2014; 114: 5572
- 1d Jain AK, Sharma S, Vaidya A, Ravichandran V, Agrawal RK. Chem. Biol. Drug Des. 2013; 81: 557
- 1e Christoforou IC, Koutentis PA, Michaelidou SS. ARKIVOC 2006; (vii): 207
- 1f Khazi IA. M, Gadad AK, Lamani RS, Bhongade BA. Tetrahedron 2011; 67: 3289
- 2a Jatav V, Mishra P, Kashaw S, Stables JP. Eur. J. Med. Chem. 2008; 43: 1945
- 2b Sharma R, Prasad Y, Mishra GP, Chaturvedi SC. Med. Chem. Res. 2014; 23: 252 DOI: 10.1007/s00044-013-0626-0
- 3a Clerici F, Pocar D, Guido M, Loche A, Perlini V, Brufani M. J. Med. Chem. 2001; 44: 931
- 3b Jubie S, Dhanabal P, Azam MA, Kumar NS, Ambhore N, Kalirajan R. Med. Chem. Res. 2015; 24: 1605 ; DOI: 10.1007/s00044-014-1235-2
- 4a Manjunatha K, Poojary B, Kumar V, Lobo PL, Fernandes J, Chandrashekhar C. Pharma Chem. 2015; 7: 207
- 4b Farghaly TA, Abdallah MA, Masaret GS, Muhammad ZA. Eur. J. Med. Chem. 2015; 97: 320
- 5a Kolavi G, Hegde V, Khazi I, Gadad P. Bioorg. Med. Chem. 2006; 14: 3069
- 5b Oruc EE, Rollas S, Kandemirli F, Shvets N, Dimoglo AS. J. Med. Chem. 2004; 47: 6760
- 5c Barday M, Janot C, Halcovitch NR, Muir J, Aïssa C. Angew. Chem. Int. Ed. 2017; 56: 13117
- 6a Salgin-Gökşen U, Gökhan-Kelekçi N, Göktaş Ö, Köysal Y, Kılıç E, Işık S, Aktay G, Özalp M. Bioorg. Med. Chem. 2007; 15: 5738
- 6b Chidananda N, Poojary B, Sumangala V, Kumari NS, Shetty P, Arulmoli T. Eur. J. Med. Chem. 2012; 51: 124
- 7 Lee J, Lee S.-H, Seo HJ, Son E.-J, Lee SH, Jung ME, Lee MW, Han HK, Kim J, Kang J, Lee J. Bioorg. Med. Chem. 2010; 18: 2178
- 8a Kumar D, Kumar NM, Chang KH, Shah K. Eur. J. Med. Chem. 2010; 45: 4664
- 8b Megally Abdo NY, Kamel MM. Chem. Pharm. Bull. 2015; 63: 369
- 9a Hasui T, Matsunaga N, Ora T, Ohyabu N, Nishigaki N, Imura Y, Igata Y, Matsui H, Motoyaji T, Tanaka T, Habuka N, Sogabe S, Ono M, Siedem CS, Tang TP, Gauthier C, De Meese LA, Boyd SA. Fukumoto S. 2011; 54: 8616
- 9b Samel AB, Pai NR. J. Chin. Chem. Soc. (Weinheim, Ger.) 2010; 57: 1327
- 10a Zoumpoulakis P, Camoutsis C, Pairas G, Soković M, Glamočlija J, Potamitis C, Pitsas A. Bioorg. Med. Chem. 2012; 20: 1569
- 10b Rezki N, Al-Yahyawi AM, Bardaweel SK, Al-Blewi FF, Aouad MR. Molecules 2015; 20: 16048
- 11a Jiang J, Li G, Zhang F, Xie H, Deng G.-J. Adv. Synth. Catal. 2018; 360: 1622
- 11b Adib M, Rajai-Daryasarei S, Pashazadeh R, Jahani M, Amanlou M. Synlett 2018; 29: 1583
- 12 Chen Z, Brown J, Drees M, Seger M, Hu Y, Xia Y, Boudinet D, McCray M, Delferro M, Marks TJ, Liao C.-Y, Ko C.-W, Chang Y.-M, Facchetti A. Chem. Mater. 2016; 28: 6390
- 13a Dai H, Ge S, Li G, Chen J, Shi Y, Ye L, Ling Y. Bioorg. Med. Chem. Lett. 2016; 26: 4504
- 13b Hayat F, Salahuddin A, Zargan J, Azam A. Eur. J. Med. Chem. 2010; 45: 6127
- 13c Chen L, Zhu Y.-J, Fan Z.-J, Guo X.-F, Zhang Z.-M, Xu J.-H, Song Y.-Q, Yurievich MY, Belskaya NP, Bakulev VA. J. Agric. Food Chem. 2017; 65: 745
- 13d Wang H, Yang Z, Fan Z, Wu Q, Zhang Y, Mi N, Wang S, Zhang Z, Song H, Liu F. J. Agric. Food Chem. 2011; 59: 628
- 13e Cikotiene I, Kazlauskas E, Matuliene J, Michailoviene V, Torresan J, Jachno J, Matulis D. Bioorg. Med. Chem. Lett. 2009; 19: 1089
- 13f Balasankar T, Gopalakrishnan M, Nagarajan S. Eur. J. Med. Chem. 2005; 40: 728
- 14a Hurd CD, Mori RI. J. Am. Chem. Soc. 1955; 77: 5359
- 14b Attanasi OA, Baccolini G, Boga C, De Crescentini L, Filippone P, Mantellini F. J. Org. Chem. 2005; 70: 4033
- 14c Hu Y, Baudart S, Porco JA. J. Org. Chem. 1999; 64: 1049
- 16 Sheehan JC, Izzo PT. J. Am. Chem. Soc. 1949; 71: 4059
- 17 Singh MS, Nagaraju A, Verma GK, Shukla G, Verma RK, Srivastava A, Raghuvanshi K. Green Chem. 2013; 15: 954
- 18 Filimonov VO, Dianova LN, Galata KA, Beryozkina TV, Novikov MS, Berseneva VS, Eltsov OS, Lebedev AT, Slepukhin PA, Bakulev VA. J. Org. Chem. 2017; 82: 4056
- 19 Zhang L, Sun B, Liu Q, Mo F. J. Org. Chem. 2018; 83: 4275
- 20 Kumar A, Muthyala MK, Choudhary S, Tiwari RK, Parang K. J. Org. Chem. 2012; 77: 9391
- 21 Chen J, Jiang Y, Yu J.-T, Cheng J. J. Org. Chem. 2016; 81: 271
- 22 Ishikawa T, Kimura M, Kumoi T, Iida H. ACS Catal. 2017; 7: 4986
- 23 Mo S.-K, Teng Q.-H, Pan Y.-M, Tang H.-T. Adv. Synth. Catal. 2019; 361: 1756
- 24 Liu BB, Bai H.-W, Liu H, Wang S.-Y, Ji S.-J. J. Org. Chem. 2018; 83: 10281
- 25a Yajima K, Yamaguchi K, Mizuno N. Chem. Commun. 2014; 50: 6748
- 25b Yoshimura A, Nguyen KC, Klasen SC, Saito A, Nemykin VN, Zhdankin VV. Chem. Commun. 2015; 51: 7835
- 25c Shah A.-ul-HA, Khan ZA, Choudhary N, Lohӧlter C, Schäfer S, Marie GP. L, Farooq U, Witulski B, Wirth T. Org. Lett. 2009; 11: 3578
- 25d Vanajatha G, Reddy VP. Tetrahedron Lett. 2016; 57: 2356
- 25e Mahajan PS, Tanpure SD, More NA, Gajbhiye JM, Mhaske SB. RSC Adv. 2015; 5: 101641
- 25f Sun Y, Wu W, Jiang H. Eur. J. Org. Chem. 2014; 4239
- 25g Davison EK, Sperry J. Org. Chem. Front. 2016; 3: 38
- 25h Frija LM. T, Pombeiro AJ. L, Kopylovich MN. Eur. J. Org. Chem. 2017; 19: 2670
- 25i Wang B, Meng Y, Zhou Y, Ren L, Wu J, Yu W, Chang J. J. Org. Chem. 2017; 82: 5898
- 25j Wang Z.-Q, Meng X.-J, Li Q.-Y, Tang H.-T, Wang H.-S, Pan Y.-M. Adv. Synth. Catal. 2018; 360: 4043
- 25k Mayhoub AS, Kiselev E, Cushman M. Tetrahedron Lett. 2011; 52: 4941
- 25l Mayhoub AS, Marler L, Kondratyuk TP, Park E.-J, Pezzuto JM, Cushman M. Bioorg. Med. Chem. 2012; 20: 510
- 26 Noei J, Khosropour AR. Tetrahedron Lett. 2013; 54: 9
- 27a Chai L, Xu Y, Ding T, Fang X, Zhang W, Wang Y, Lu M, Xu H, Yang X. Org. Biomol. Chem. 2017; 15: 8410
- 27b Tumula N, Krishna PR, Balasubramanian S, Nakka M. Adv. Synth. Catal. 2018; 360: 2806
- 27c Chai L, Lai Z, Xia Q, Yuan J, Bian QM. Yu, Zhang W, Xu Y, Xu H. Eur. J. Org. Chem. 2018; 4338
- 28 Kim H.-Y, Kwak SH, Lee G.-H, Gong Y.-D. Tetrahedron 2014; 70: 8737
- 29 Yang L, Song L, Tang S, Li L, Li H, Yuan B, Yang G. Eur. J. Org. Chem. 2019; 1281
- 30 Xie H, Cai J, Wang Z, Huang H, Deng G.-J. Org. Lett. 2016; 18: 2196
- 31 Wang Z, Xie H, Xiao F, Guo Y, Huang H, Deng G.-J. Eur. J. Org. Chem. 2017; 1604
- 32 Zhou Z, Liu M, Sun S, Yao E, Liu S, Wu Z, Yu J.-T, Jiang Y, Cheng J. Tetrahedron Lett. 2017; 58: 2571
- 33 Tumula N, Jatangi N, Palakodety RK, Balasubramanian S, Nakka M. J. Org. Chem. 2017; 82: 5310
- 34 Yu W, Huang Y, Li J, Tang X, Wu W, Jiang H. J. Org. Chem. 2018; 83: 9334
- 35 Hu Y, Li C.-Y, Wang X.-M, Yang Y.-H, Zhu H.-L. Chem. Rev. 2014; 114: 5572
- 36 Yang S.-J, Lee S.-H, Kwak H.-J, Gong Y.-D. J. Org. Chem. 2013; 78: 438
- 37 Niu P, Kang J, Tian X, Song L, Liu H, Wu J, Yu W, Chang J. J. Org. Chem. 2015; 80: 1018
- 38 Singh SJ, Rajamanickam S, Gogoi A, Patel BK. Tetrahedron Lett. 2016; 57: 1044
- 39 Zhou Z, Liu Y, Chen J, Yao E, Cheng J. Org. Lett. 2016; 18: 5268
- 40 Zarei M. Tetrahedron 2017; 73: 1867
- 41a Koutentis PA. In Science of Synthesis, Vol 13. Storr RC, Gilchrist TL. Thieme; Stuttgart: 2003. Chap. 13.11, 297
- 41b Koutentis PA. In Comprehensive Heterocyclic Chemistry III, Vol. 5. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Oxford: 2008. Chap. 5.09, 515
- 41c Todres ZV. Chalcogenadiazoles: Chemistry and Applications . CRC Press; Boca Raton; Chap. 2,; 53:
- 41d Konstantinova LS, Knyazeva EA, Rakitin OA. Org. Prep. Proced. Int. 2014; 46: 475
- 42a Zibarev AV, Mews R. In Selenium and Tellurium Chemistry: From Small Molecules to Biomolecules and Materials . Woollins JD, Laitinen RS. Springer; Berlin: 2011: 123
- 42b Gritsan NP, Zibarev AV. Izv. Akad. Nauk., Ser. Khim. 2011; 2091 ; Russ. Chem. Bull. 2011, 60, 2131
- 43 Konstantinov LS, Bol’shakov OI, Obruchnikova NV, Golova SP, Nelyubina YV, Lyssenko KA, Rakitin OA. Tetrahedron 2010; 66: 4330
- 44 Rakitin OA, Zibarev AV. Asian J. Org. Chem. 2018; 7: 2397
- 45 Konstantinova LS, Knyazeva EA, Obruchnikova NV, Gatilov YV, Zibarev AV, Rakitin OA. Tetrahedron Lett. 2013; 54: 3075
- 46a Konstantinova LS, Knyazeva EA, Obruchnikova NV, Vasilieva NV, Irtegova IG, Nelyubina YV, Bagryanskaya IY, Shundrin LA, Sosnovskaya ZY, Zibarev AV, Rakitin OA. Tetrahedron 2014; 70: 5558
- 46b Konstantinova LS, Knyazeva EA, Rakitin OA. Molecules 2015; 20: 14522
- 47 Kalogirou AS, Kourtellaris A, Koutentis PA. Org. Lett. 2016; 18: 4056
For reviews, see: