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Synthesis 2019; 51(20): 3765-3783
DOI: 10.1055/s-0037-1611863
DOI: 10.1055/s-0037-1611863
review
Recent Advances in the Synthesis of 5-Substituted 1H-Tetrazoles: A Complete Survey (2013–2018)
R.M. gratefully acknowledges University of Delhi for award of Non-Net Fellowship. S.K.A. acknowledges University of Delhi and DST Purse Grant Phase-II for research grant.Further Information
Publication History
Received: 06 April 2019
Accepted after revision: 16 May 2019
Publication Date:
01 July 2019 (online)
Dedicated in the memory of my beloved brother, the late Mr. Sushil Kumar Awasthi.
Abstract
Tetrazoles are synthetic organic heterocyclic compounds comprising of high nitrogen content among stable heterocycles. Tetrazoles, chiefly 5-substituted 1H-tetrazoles have been used as a bioisosteric replacement for carboxylic acids in medicinal chemistry. Various clinical drugs, including losartan, cefazolin, and alfentanil, contain the tetrazole moiety. There have been significant developments in the synthesis of 5-substituted 1H-tetrazoles. Researchers are still working to develop more efficient and ecofriendly methods for their synthesis. In this review, we provide a comprehensive discussion of the recent advancements in the field of synthesis of 5-substituted 1H-tetrazoles.
1 Introduction
2 The Role of 5-Substituted 1H-Tetrazoles in Medicinal Chemistry
3 Synthesis of 5-Substituted 1H-Tetrazoles
3.1 Microwave-Assisted Synthesis
3.2 Heterogeneous Catalysts
3.3 Nanoparticles as Heterogeneous Catalysts
3.4 Miscellaneous Methods
4 Sartans: A Class of Tetrazole-Based Commercial Drugs
5 Conclusions
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References
- 1 Bladin JA. Ber. Dtsch. Chem. Ges. 1885; 18: 1544
- 2 Bamberger E, De Gruyter P. Ber. Dtsch. Chem. Ges. 1893; 26: 2385
- 3 Butler RN. In Comprehensive Heterocyclic Chemistry II . Katritzky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996: 897
- 4 Jursic BS, Le Blanc BW. J. Heterocycl. Chem. 1998; 35: 405
- 5a Koldobskii GI, Ostrovskii VA. Usp. Khim. 1994; 63: 847
- 5b Izsák D, Klapötke TM, Lutter FH, Pflüger C. Eur. J. Inorg. Chem. 2016; 2016: 1720
- 5c Kumar D, He C, Mitchell LA, Parrish DA, Shreeve JM. J. Mater. Chem. A 2016; 4: 9220
- 5d Tang Y, He C, Imler GH, Parrish DA, Shreeve JM. J. Mater. Chem. A 2016; 4: 13923
- 5e Szimhardt N, Bölter MF, Born M, Klapötke TM, Stierstorfer J. Dalton Trans. 2017; 46: 5033
- 5f Kumar D, Imler GH, Parrish DA, Shreeve JM. J. Mater. Chem. A 2017; 5: 16767
- 5g Szimhardt N, Wurzenberger MH. H, Spieß P, Klapötke TM, Stierstorfer J. Propellants, Explos., Pyrotech. 2018; 43: 1
- 6 Ostrovskii VA, Pevzner MS, Kofman TP, Shcherbinin MB, Tselinskii IV. Targets Heterocycl. Syst. 1999; 3: 467
- 7 Singh H, Chawla AS, Kapoor VK, Paul D, Malhotra RK. Prog. Med. Chem. 1980; 17: 151
- 8 Okabayashi T, Kano H, Makisumi Y. Chem. Pharm. Bull. 1960; 8: 157
- 9 Sangal SK, Kumar A. J. Indian Chem. Soc. 1986; 63: 351
- 10 Witkowski JK, Robin RK, Sidwell RW, Simon LN. J. Med. Chem. 1972; 15: 1150
- 11 Barry VC, Conalty ML, O’Sullivan JP, Twomey D. Antitumour Activity of Tetrazolopyridazines and Tetrazolophthalazines . In Chemotherapy, Vol. 8. Williams JD, Geddes AM. Plenum Press; New York: 1976. 103
- 12 Maxwell JR, Wasdahl DA, Wolfson AC, Stenberg VI. J. Med. Chem. 1984; 27: 1565
- 13 Stewart KD. Bioorg. Med. Chem. Lett. 1998; 8: 529
- 14 Shishoo CJ, Devani MB, Karvekar MD, Vilas GV, Anantham S, Bhaati VS. Indian J. Chem., Sect. B 1982; 21: 666
- 15 Ray SM, Lahiri SC. J. Indian Chem. Soc. 1990; 67: 324
- 16 Sarro AD, Ammendola D, Zappala M, Grasso S, Sarro GB. D. Antimicrob. Agents Chemother. 1995; 39: 232
- 17 Mavromoustakos T, Kolocouris A, Zervou M, Roumelioti P, Matsoukas J, Weisemann R. J. Med. Chem. 1999; 42: 1714
- 18 Hayao S, Havera HJ, Strycker WG, Leipzig TJ, Rodriguez R. J. Med. Chem. 1965; 10: 400
- 19 Akimoto H, Ootsu K, Itoh F. EP 0530537, 1993 ; Chem. Abstr. 1993, 119, 226417.
- 20 Venkateshwarlu G, Rajanna KC, Saipprakash PK. Synth. Commun. 2009; 39: 426
- 21 Abell AD, Foulds GJ. J. Chem. Soc., Perkin Trans. 1 1997; 2475
- 22 Tamura Y, Watanabe F, Nakatani T, Yasui K, Fuji M, Komurasaki T, Tsuzuki H, Maekwa R, Yoshioka T, Kawada K, Sugita K, Ohtani M. J. Med. Chem. 1998; 41: 640
- 23 Sandmann G, Schneider C, Boger P. Z. Naturforsch., C 1996; 51: 534
- 24a Moderhack D. J. Prakt. Chem. 1998; 340: 687
- 24b Novakova V, Roh J, Gela P, Kunes J, Zimcik P. Chem. Commun. 2012; 48: 4326
- 25a Wittenberger SJ. Org. Prep. Proced. Int. 1994; 26: 499
- 25b Patani GA, LaVoie EJ. Chem. Rev. 1996; 96: 3147
- 26a Roh J, Vávrová K, Hrabálek A. Eur. J. Org. Chem. 2012; 2012: 6101 ; and references therein
- 26b Ostrovskii VA, Koldobskii GI, Shirokova NP, Poplavskii VS. Khim. Geterotsikl. Soedin. 1981; 4: 559
- 26c Hansch C, Leo A, Hoekman DA. Exploring QSAR. American Chemical Society; Washington, DC: 1995
- 27 Trifonov RE, Ostrovskii VA. Russ. J. Org. Chem. 2006; 42: 1585
- 28 Liljebris C, Larsen SD, Ogg D, Palazuk BJ, Bleasdale JE. J. Med. Chem. 2002; 45: 1785
- 29 Herr RJ. Bioorg. Med. Chem. 2002; 10: 3379
- 30 Kraus JL. Pharmacol. Res. Commun. 1983; 15: 183
- 31 Kraus JL, Faury P, Charvet AS, Camplo M. Res. Commun. Chem. Pathol. Pharmacol. 1994; 83: 209
- 32 Benson FR. Chem. Rev. 1947; 41: 1
- 33 Hantzsch A, Vagt A. Justus Liebigs Ann. Chem. 1901; 314: 339
- 34a Mihina JS, Herbst RM. J. Org. Chem. 1950; 15: 1082
- 34b Herbst RM, Wilson KR. J. Org. Chem. 1957; 22: 1142
- 35 Finnegan WG, Henry RA, Lofquist R. J. Am. Chem. Soc. 1958; 80: 3908
- 36 Kumar A, Narayanan R, Shechter H. J. Org. Chem. 1996; 61: 4462
- 37 Demko ZP, Sharpless KB. J. Org. Chem. 2001; 66: 7945
- 38a Himo F, Demko ZP, Noodleman L, Sharpless KB. J. Am. Chem. Soc. 2002; 124: 12210
- 38b Demko ZP, Sharpless KB. Org. Lett. 2002; 4: 2525
- 38c Himo F, Demko ZP, Noodleman L, Sharpless KB. J. Am. Chem. Soc. 2003; 125: 9983
- 38d Bonnamour J, Bolm C. Chem. Eur. J. 2009; 15: 4543
- 38e Esirden I, Başar E, Kaya M. Chem. Pap. 2015; 69: 1231
- 39a Bosch L, Vilarrasa J. Angew. Chem. Int. Ed. 2007; 46: 3926
- 39b Kumar S, Dubey S, Saxena N, Awasthi SK. Tetrahedron Lett. 2014; 55: 6034
- 40 Schmidt B, Meid D, Kieser D. Tetrahedron 2007; 63: 492
- 41a Kantam ML, Kumar KB. S, Sridhar C. Adv. Synth. Catal. 2005; 347: 1212
- 41b Sreedhar B, Kumar SA, Yada D. Tetrahedron Lett. 2011; 52: 3565
- 41c Lang L, Zhou H, Xue M, Wang X, Xu Z. Mater. Lett. 2013; 106: 443
- 41d Rama V, Kanagaraj K, Pitchumani K. J. Org. Chem. 2011; 76: 9090
- 41e Dehghani F, Sardarian AR, Esmaeilpour M. J. Organomet. Chem. 2013; 743: 87
- 41f Mani P, Sharma C, Kumar S, Awasthi SK. J. Mol. Catal. A: Chem. 2014; 392: 150
- 41g Kumar S, Kumar A, Agarwal A, Awasthi SK. RSC Adv. 2015; 5: 21651
- 41h Qi G, Zhang W, Dai Y. Res. Chem. Intermed. 2015; 41: 1149
- 41i Nasrollahzadeh M, Jalehb B, Jabbarib A. RSC Adv. 2014; 4: 36713
- 41j Esirden I, Erken E, Kaya M, Sen F. Catal. Sci. Technol. 2015; 5: 4452
- 41k Kumar A, Kumar S, Khajuria Y, Awasthi SK. RSC Adv. 2016; 6: 75227
- 42a Microwaves in Organic Synthesis, 2nd ed. Loupy A. Wiley-VCH; Weinheim: 2006
- 42b Microwave Assisted Organic Synthesis . Tierney JP, Lindström P. Blackwell; Oxford: 2005
- 42c Bogdal D. Microwave-Assisted Organic Synthesis: One Hundred Reaction Procedures. Elsevier; Amsterdam: 2005
- 42d Kappe CO, Stadler A. Microwaves in Organic and Medicinal Chemistry . Wiley-VCH; Weinheim: 2005
- 42e Kappe CO. Angew. Chem. Int. Ed. 2004; 43: 6205
- 42f Hayes BL. Aldrichimica Acta 2004; 37: 66
- 42g Roberts BA, Strauss CR. Acc. Chem. Res. 2005; 38: 653
- 43 Yoneyama H, Usami Y, Komeda S, Harusawa S. Synthesis 2013; 45: 1051
- 44 El-Remaily MA. A, Mohamed SK. Tetrahedron 2014; 70: 270
- 45 Coca A, Turek E, Feinn L. Synth. Commun. 2015; 45: 218
- 46 Coca A, Feinn L, Dudley J. Synth. Commun. 2015; 45: 1023
- 47 Yıldız Y, Esirden I, Erken E, Demir E, Kaya M, Sen F. ChemistrySelect 2016; 1: 1695
- 48 Joshi SM, Mane RB, Pulagam KR, Gomez-Vallejo V, Llop J, Rode C. New J. Chem. 2017; 41: 8084
- 49 Shelkar R, Singh A, Nagarkar J. Tetrahedron Lett. 2013; 54: 106
- 50 Meshram GA, Deshpande SS, Wagh PA, Vala VA. Tetrahedron Lett. 2014; 55: 3557
- 51 Wang Z, Liu Z, Cheon SH. Bull. Korean Chem. Soc. 2015; 36: 198
- 52 Razavi N, Akhlaghinia B. RSC Adv. 2015; 5: 12372
- 53 Ghodsinia SS. E, Akhlaghinia B. RSC Adv. 2015; 5: 49849
- 54 Jahanshahi R, Akhlaghinia B. RSC Adv. 2015; 5: 104087
- 55 Nikoorazm M, Ghorbani-Choghamarani A, Khanmoradi M. Appl. Organomet. Chem. 2016; 30: 705
- 56 Kazemnejadi M, Sardarian AR. RSC Adv. 2016; 6: 91999
- 57 Rekunge DS, Indalkar KS, Chaturbhuj GU. Tetrahedron Lett. 2016; 57: 5815
- 58 Kolo K, Sajadi SM. Lett. Org. Chem. 2013; 10: 688
- 59 Sharghi H, Ebrahimpourmoghaddam S, Doroodmand MM. J. Organomet. Chem. 2013; 738: 41
- 60 Esmaeilpour M, Javidi J, Dodeji FN, Abarghoui MM. J. Mol. Catal. A: Chem. 2014; 393: 18
- 61 Akula RK, Adimulam C, Gangaram S, Kengiri R, Banda N, Pamulaparthy SR. Lett. Org. Chem. 2014; 11: 440
- 62 Abdollahi-Alibeik M, Moaddeli A. New J. Chem. 2015; 39: 2116
- 63 Abdollahi-Alibeik M, Moaddeli A. J. Chem. Sci. 2016; 128: 93
- 64 Zamani L, Mirjalili BB. F, Zomorodian K, Zomorodian S. S. Afr. J. Chem. 2015; 68: 133
- 65 Erken E, Esirden I, Kaya M, Sen F. RSC Adv. 2015; 5: 68558
- 66 Zarghani M, Akhlaghinia B. RSC Adv. 2016; 6: 31850
- 67 Ghorbani-Choghamarani A, Shiri L, Azadi G. RSC Adv. 2016; 6: 32653
- 68 Abrishami F, Ebrahimikia M, Rafiee F. Iran. J. Catal. 2016; 6: 245
- 69 Esmaeilpour M, Javidi J, Zahmatkesh S. Appl. Organomet. Chem. 2016; 30: 897
- 70 Baskaya G, Esirden I, Erken E, Sen F, Kaya M. J. Nanosci. Nanotechnol. 2017; 17: 1992
- 71 Azadi G, Ghorbani-Choghamarani A, Shiri L. Transition Met. Chem. (Dordrecht, Neth.) 2017; 42: 131
- 72 Soltan Rad MN, Behrouz S, Dehchenari VS, Hoseini SJ. J. Heterocycl. Chem. 2017; 54: 355
- 73 Moradi P, Ghorbani-Choghamarani A. Appl. Organomet. Chem. 2017; 31: 3602
- 74 Hajjami M, Nejat R, Sharifirad F, Gholamian F. Org. Chem. Res. 2018; 4: 23
- 75 Sardarian AR, Eslahi H, Esmaeilpour M. ChemistrySelect 2018; 3: 1499
- 76 Nikoorazm M, Ghorbani-Choghamaranai A, Khanmoradi M, Moradi P. J. Porous Mater. 2018; 25: 1831
- 77 Sridhar M, Mallu KK. R, Jillella R, Godala KR, Beeram CR, Chinthala N. Synthesis 2013; 45: 507
- 78 Fazeli A, Oskooie HA, Beheshtiha YS, Heravi MM, Valizadeh H, Bamoharram FF. Monatsh. Chem. 2013; 144: 1407
- 79 Patil DR, Wagh YB, Ingole PG, Singh K, Dalal DS. New J. Chem. 2013; 37: 3261
- 80 Szeijtli J. Cyclodextrin Technology . Kluwer Academic Publishers; Dordrecht: 1998: 26
- 81 Villalonga R, Cao R, Fragoso A. Chem. Rev. 2007; 107: 3088
- 82 Hapiot F, Tilloy S, Monflier E. Chem. Rev. 2006; 106: 767
- 83 Sampath A, Reddy VP, Chakravarthy AK, Reddy PP. Asian J. Chem. 2013; 25: 393
- 84 Yao YW, Zhou Y, Lin BP, Yao C. Tetrahedron Lett. 2013; 54: 6779
- 85 Vorona S, Artamonova T, Zevatskii Y, Myznikov L. Synthesis 2014; 46: 781
- 86 Mahkam M, Namazifar Z, Nabati M, Aboudi J. Iran. J. Org. Chem. 2014; 6: 1217
- 87 Coca A, Turek E. Tetrahedron Lett. 2014; 55: 2718
- 88 Mani P, Singh AK, Awasthi SK. Tetrahedron Lett. 2014; 55: 1879
- 89 Nanjundaswamy HM, Abrahamse H. Heterocycles 2014; 89: 2137
- 90 Nowrouzi N, Farahi S, Irajzadeh M. Tetrahedron Lett. 2015; 56: 739
- 91 Sivaguru P, Theerthagiri P, Lalitha A. Tetrahedron Lett. 2015; 56: 2203
- 92 Tao C, Wang B, Sun L, Yi J, Shi D, Wang J, Liu W. J. Chem. Res. 2017; 41: 25
- 93 Guggilapu SD, Prajapti SK, Nagarsenkar A, Gupta KK, Babu BN. Synlett 2016; 27: 1241
- 94 Kant R, Singh V, Agarwal A. C. R. Chim. 2016; 19: 306
- 95 Ishihara K, Kawashima M, Shioiri T, Matsugi M. Synlett 2016; 27: 2225
- 96 Padvi SA, Dalal DS. Synth. Commun. 2017; 47: 779
- 97 Bhosle MR, Shaikh DS, Khillare LD, Deshmukh AR, Mane RA. Synth. Commun. 2017; 47: 695
- 98 Yakambram B, Shree AJ, Reddy LS, Satyanarayana T, Naveen P, Bandichhor R. Tetrahedron Lett. 2018; 59: 445
- 99 Bhagat SB, Telvekar VN. Synlett 2018; 29: 874
- 100 Mehraban JA, Azizi K, Jalali MS, Heydari A. ChemistrySelect 2018; 3: 116
- 101 Parr MK, Joseph JF. J. Pharm. Biomed. Anal. 2019; 164: 536
- 102 Penikelapati HR, Ambati S, Maruthikumar TV, Ambati NB. Res. J. Pharm. Biol. Chem. Sci. 2011; 2: 632
- 103 Aalla S, Gilla G, Bojja Y, Anumula RR, Vummenthala PR, Padi PR. Org. Process Res. Dev. 2012; 16: 682
- 104a Harel Z, Rukhman I. US Patent 7378531B2, 2008
- 104b Yongjun T, Zhang Y, Meijun L, Rongde C, Gao W. CN Patent 100522953C, 2009
- 104c Chinta RR, Nangi GB. S, Nayini MR, Yallapa SS, Budidet SR, Aminul I, Meenakshisunderam S. US Patent 8981109B2, 2015
- 104d Zupancic S. WO Patent 2011124655A1, 2011
- 105a Ghosh S, Kumar AS, Soundararajan R, Mehta GN. Synth. Commun. 2009; 39: 3880
- 105b Seki M. ACS Catal. 2011; 1: 607
- 105c Wang G.-x, Sun B.-p, Peng C.-h. Org. Process Res. Dev. 2011; 15: 986
- 105d Ambati S, Penikelapati HR, Maruthikumar TV, Ambati NB. Pharma Chem. 2011; 3: 13
- 105e Seki M, Nagahama M. J. Org. Chem. 2011; 76: 10198
- 105f Hubrich J, Ackermann L. Eur. J. Org. Chem. 2016; 2016: 3700
- 106 Hagenbuch J.-P. Chimia 2003; 57: 773
- 107 Xiaoren Z, Nianping S, Wenling Z, Peng W. CN Patent 104045602A, 2014
- 108 Guidelines for Drinking-Water Quality, 4th ed. incorporating the 1st addendum. World Health Organization; Geneva: 2017. ; https://apps.who.int/iris/bitstream/10665/254637/1/9789241549950-eng.pdf (accessed May 31, 2019)
- 109 N-Nitrosodimethylamine In Drinking-water. Background Document for Preparation of WHO Guidelines for Drinking-water Quality. World Health Organization; Geneva: 2008. http://www.who.int/water_sanitation_health/dwq/chemicals/ ndma_2add_feb2008.pdf (accessed May 31, 2019)
- 110 IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans – Some N-Nitroso Compounds. International Agency for Research on Cancer; Lyon: 1978. https://monographs.iarc.fr/wp-content/uploads/2018/06/mono17.pdf (accessed May 31, 2019)
- 111 Mitch WA, Sharp JO, Trussell RR, Valentine RL, Alvarez-Cohen L, Sedlak DL. Environ. Eng. Sci. 2003; 20: 389
- 112 Andrzejewski P, Kasprzyk-Hordern B, Nawrocki J. Desalination 2005; 176: 37
- 113 Preussmann R. Naturwissenschaften 1984; 71: 25