Subscribe to RSS
DOI: 10.1055/s-0042-1751526
Recent Advances in the Multicomponent Synthesis of Heterocycles Using 5-Aminotetrazole
Abstract
The unique reactivity and beneficial features of the 5-aminotetrazole synthon (1H-tetrazol-5-amine) have made it a versatile and effective building block in the synthesis of heterocyclic compounds. In addition, several drugs containing this scaffold with a wide array of biological properties have been already introduced. Heterocyclic structures are the backbone of many biologically active and industrially important compounds. 5-Aminotetrazole is one of the favored synthons used in the preparation of heterocycle-bearing compounds, especially in multicomponent synthesis. This review highlights a comprehensive overview of the emerging applications of 5-aminotetrazole as a key component in the synthesis of heterocyclic frameworks through multicomponent reactions, reported between 2017 and July 2023.
1 Introduction
2 5-Aminotetrazole
3 Tetrazolopyrimidine Compounds
4 Spiro Compounds
5 Miscellaneous
6 Conclusion
Key words
1H-tetrazol-5-amine - 5-aminotetrazole - heterocycles - multicomponent reactions - synthesisPublication History
Received: 24 August 2023
Accepted after revision: 24 October 2023
Article published online:
08 January 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Zhang TY. Adv. Heterocycl. Chem. 2017; 121: 1
- 2 Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
- 3 Baumann M, Baxendale IR. Beilstein J. Org. Chem. 2013; 9: 2265
- 4 Kim J, Movassaghi M. Chem. Soc. Rev. 2009; 38: 3035
- 5 Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
- 6 Da Pieve C, Makarem A, Turnock S, Maczynska J, Smith G, Kramer-Marek G. Molecules 2020; 25: 1562
- 7 Klika KD, Da Pieve C, Kopka K, Smith G, Makarem A. Org. Biomol. Chem. 2021; 19: 1722
- 8 Koley M, Han J, Soloshonok V, Mojumder S, Javahershenas R, Makarem A. RSC Med. Chem. 2023; in press
- 9 Rotstein BH, Zaretsky S, Rai V, Yudin AK. Chem. Rev. 2014; 114: 8323
- 10 Ghashghaei O, Seghetti F, Lavilla R. Beilstein J. Org. Chem. 2019; 15: 521
- 11 Multicomponent Reactions in Organic Synthesis . Zhu J, Wang Q, Wang MX. Wiley-VCH; Weinheim: 2015
- 12 Science of Synthesis: Multicomponent Reactions 1 . Müller TJ. J. Thieme; Stuttgart: 2014
- 13 Cioc RC, Ruijter E, Orru RV. A. Green Chem. 2014; 16: 2958
- 14 Jampilek J. Molecules 2019; 24: 3839
- 15 Kerru N, Gummidi L, Maddila S, Gangu KK, Jonnalagadda SB. Molecules 2020; 25: 1909
- 16 Taylor AP, Robinson RP, Fobian YM, Blakemore DC, Jones LH, Fadeyi O. Org. Biomol. Chem. 2016; 14: 6611
- 17 Szimhardt N, Wurzenberger MH. H, Spieß P, Klapötke TM, Stierstorfer J. Propellants, Explos., Pyrotech. 2018; 43: 1
- 18 Akimoto H, Ootsu K, Itoh F. EP 0530537, 1993
- 19 Hayao S, Havera HJ, Strycker WG, Leipzig TJ, Rodriguez R. J. Med. Chem. 1967; 10: 400
- 20 Sangal SK, Kumar A. J. Indian Chem. Soc. 1986; 63: 351
- 21 Szulczyk D, Dobrowolski MA, Roszkowski P, Bielenica A, Stefanska J, Kolinski M, Kmiecik S, Jozwiak M, Wrzosek M, Olejarz W, Struga M. Eur. J. Med. Chem. 2018; 156: 631
- 22 Gao F, Xiao J, Huang G. Eur. J. Med. Chem. 2019; 184: 111744
- 23 Barry VC, Conalty ML, O’Sullivan JF, Twomey D. Antitumour Activity of Tetrazolopyridazines and Tetrazolophthalazines . In Chemotherapy, Vol 8. Hellmann K, Connors TA. Springer; Boston MA: 1976
- 24 Stewart KD, Loren S, Frey L, Otis E, Klinghofer V, Hulkower KI. Bioorg. Med. Chem. Lett. 1998; 8: 529
- 25 Abell AD, Foulds GJ. J. Chem. Soc., Perkin Trans. 1 1997; 2475
- 26 Ray SM, Lahiri SC. J. Indian Chem. Soc. 1990; 67: 324
- 27 Sarro AD, Ammendola D, Zappala M, Grasso S, Sarro GB. D. Antimicrob. Agents Chemother. 1995; 39: 232
- 28 Wang SB, Deng XQ, Zheng Y, Yuan YP, Quan ZS, Guan LP. Eur. J. Med. Chem. 2012; 56: 139
- 29 Mavromoustakos T, Kolocouris A, Zervou M, Roumelioti P, Matsoukas J, Weisemann R. J. Med. Chem. 1999; 42: 1714
- 30 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
- 31 Javahershenas R, Nikzat S. RSC Adv. 2023; 13: 16619
- 32 Javahershenas R. J. Mol. Liq. 2023; 385: 122398
- 33 Imeni S, Makarem A, Javahershenas R. Asian J. Org. Chem. 2023; 12: e202300303
- 34 Javahershenas R. Mol. Diversity 2023; 27: 2399
- 35 Majidi Arlan F, Poursattar Marjani A, Javahershenas R, Khalafy J. New J. Chem. 2021; 45: 12328
- 36 Javahershenas R. ARKIVOC 2021; (i): 236
- 37 Neochoritis CG, Zhao T, Domling A. Chem. Rev. 2019; 119: 1970
- 38 Murlykina MV, Morozova AD, Zviagin IM, Sakhno YI, Desenko SM, Chebanov VA. Front. Chem. 2018; 6: 527
- 39 Imtiaz S, Ahmad War JA. Banoo S, Khan S. RSC Adv. 2021; 11: 11083
- 40 Ostrovskii VA, Popova EA, Trifonov RE. Adv. Heterocycl. Chem. 2017; 123: 1
- 41 Sakhno YI, Desenko SM, Shishkina SV, Shishkin OV, Sysoyev DO, Groth U, Kappe CO, Chebanov VA. Tetrahedron 2008; 64: 11041
- 42 Dolzhenko AV. Heterocycles 2017; 94: 1819
- 43 Lim FP. L, Luna G, Dolzhenko AV. Tetrahedron Lett. 2015; 56: 7016
- 44 Lim FP. L, Luna G, Dolzhenko AV. Tetrahedron Lett. 2014; 55: 5159
- 45 Kalinina SA, Kalinin DV, Dolzhenko AV. Tetrahedron Lett. 2013; 54: 5537
- 46 Dolzhenko AV, Kalinina SA, Kalinin DV. RSC Adv. 2013; 3: 15850
- 47 Gladkov ES, Chebanov VA, Desenko SM, Shishkin OV, Shishkina SV, Dallinger D, Kappe CO. Heterocycles 2007; 73: 469
- 48 Domling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083
- 49 Wang Y, Patil P, Domling A. Synthesis 2016; 48: 3701
- 50 Chaudhari PS, Pathare SP, Akamanchi KG. O. J. Org. Chem. 2012; 77: 3716
- 51 Tymtsunik AV, Bilenko VA, Kokhan SO, Grygorenko OO, Volochnyuk DM, Komarov IV. J. Org. Chem. 2012; 77: 1174
- 52 Nasrollahzadeh M, Habibi D, Shahkarami Z, Bayat Y. Tetrahedron 2009; 65: 10715
- 53 Congreve MS. Synlett 1996; 359
- 54 Sathishkumar M, Shanmugavelan P, Nagarajan S, Dinesh M, Ponnuswamy A. New J. Chem. 2013; 37: 488
- 55 Karaghiosoff K, Klapo TM, Mayer P, Piotrowski H, Polborn K, Willer RL, Weigand JJ. J. Org. Chem. 2006; 71: 1295
- 56 Joo Y, Shreeve JM. Org. Lett. 2008; 10: 4665
- 57 Miller AE, Feeney DJ, Ma Y, Zarcone L, Aziz MA, Magnuson E. Synth. Commun. 1990; 20: 217
- 58 Erle H.-E. Liebigs Ann. Chem. 1982; 1982: 201
- 59 Katritzky AR, Rogovoy BV, Kovalenko KV. J. Org. Chem. 2003; 68: 4941
- 60 Pathare RS, Ansari AJ, Verma S, Maurya A, Maurya AK, Agnihotri VK, Sharon A, Pardasani RT, Sawant DM. J. Org. Chem. 2018; 83: 9530
- 61 Koldobskii GI, Ostrovskii VA. Usp. Khim. 1994; 63: 847
- 62 Izsák D, Klapötke TM, Lutter FH, Pflüger C. Eur. J. Inorg. Chem. 2016; 2016: 1720
- 63 Kumar D, He C, Mitchell LA, Parrish DA, Shreeve JM. J. Mater. Chem. A 2016; 4: 9220
- 64 Tang Y, He C, Imler GH, Parrish DA, Shreeve JM. J. Mater. Chem. A 2016; 4: 13923
- 65 Szimhardt N, Bölter MF, Born M, Klapötke TM, Stierstorfer J. Dalton Trans. 2017; 46: 5033
- 66 Kumar D, Imler GH, Parrish DA, Shreeve JM. J. Mater. Chem. A 2017; 5: 16767
- 67 Sarvary A, Maleki A. Mol. Diversity 2015; 19: 189
- 68 Maleki A, Sarvary A. RSC Adv. 2015; 5: 60938
- 69 Ostrovskii VA, Trifonov RE, Popova EA. Russ. Chem. Bull. 2012; 61: 768
- 70 Ibarra IA, Islas-Jacome A, Gonzalez-Zamora E. Org. Biomol. Chem. 2018; 16: 1402
- 71 Demko ZP, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2110
- 72 Leduskrasts K. Chem. Heterocycl. Compd. 2016; 52: 533
- 73 Verma F, Sahu A, Singh PK, Rai A, Singh M, Rai VK. Green Chem. 2018; 20: 3783
- 74 Domling A, Beck B, Fuchs T, Yazbak A. J. Comb. Chem. 2006; 8: 872
- 75 Al-Hourani BJ, Sharma SK, Mane JY, Tuszynski J, Baracos V, Kniess T, Suresh M, Pietzsch J, Wuest F. Bioorg. Med. Chem. Lett. 2011; 21: 1823
- 76 Jawabrah Al-HouraniB, Al-Awaida W, Matalka KZ, El-Barghouthi MI, Alsoubani F, Wuest F. Bioorg. Med. Chem. Lett. 2016; 26: 4757
- 77 Badder EW. Angew. Chem. 1959; 71: 373
- 78 Jursic BS, Le Blanc BW. J. Heterocycl. Chem. 1998; 35: 405
- 79 Ostrovskii VA, Pevzner MS, Kofman TP, Shcherbinin MB, Tselinskii IV. Targets Heterocycl. Syst. 1999; 3: 467
- 80 Sandmann G, Schneider C, Boger P. Z. Naturforsch., C 1996; 51: 534
- 81 Wei C.-X, Bian M, Gong G.-H. Molecules 2015; 20: 5528
- 82 Frija LM. T, Ismael A, Cristiano ML. S. Molecules 2010; 15: 3757
- 83 Myznikov LV, Hrabalek A, Koldobskii GI. Chem. Heterocycl. Compd. 2007; 43: 1
- 84 Lv F, Liu Y, Zou J, Zhang D, Yao Z. Dyes Pigm. 2006; 68: 211
- 85 Song W, Wang Y, Qu J, Madden MM, Lin QA. Angew. Chem. Int. Ed. 2008; 47: 2832
- 86 Vyas A, Sahu B, Pathania Sh, Nandi NK, Chauhan G, Asati V, Kumar B. J Heterocycl. Chem. 2023; 60: 1081
- 87 Desenko SM, Gorobets MY, Lipson VV, Sakhno YI, Chebanov VA. Chem. Rec. 2023; in press
- 88 Thompson MJ, Chen B. J. Org. Chem. 2009; 74: 7084
- 89 Zhao T, Boltjes A, Herdtweck E, Domling A. Org. Lett. 2013; 15: 639
- 90 Zarganes-Tzitzikas T, Patil P, Khoury K, Herdtweck E, Domling A. Eur. J. Org. Chem. 2015; 2015: 51
- 91 Ugi I, Meyr R. US 3065241A, 1962
- 92 Shaaban S, Abdel-Wahab BF. Mol. Diversity 2016; 20: 233
- 93 Patil P, de Haan M, Kurpiewska K, Kalinowska-Tłuscik J, Domling A. ACS Comb. Sci. 2016; 18: 170
- 94 Ghorbani-Vaghei R, Alavinia S, Sarmast N. Appl. Organomet. Chem. 2017; 32: e4038
- 95 Basha SF, Prasad TN, Gudise VB, Kumar VS, Mulakayala N, Anwar S. Synth. Commun. 2019; 49: 3181
- 96 Taib LA, Keshavarz M. Polyhedron 2022; 213: 115630
- 97 Klika KD, Alsalim R, Eftekhari M, Makarem A. Dalton Trans. 2022; 51: 12436
- 98 Makarem A, Klika KD, Litau G, Remde Y, Kopka K. J. Org. Chem. 2019; 84: 7501
- 99 Taib LA, Keshavarz M. J. Porous Mater. 2023; 30: 565
- 100 Devasia J, Nizam A, Muthukumar D, Pillai RS, Joy F. J. Mol. Liq. 2023; 376: 121510
- 101 Gein VL, Prudnikova AN, Kurbatova AA, Dmitriev MV, Novikova VV, Rudakova IP, Starikov AL. Russ. J. Gen. Chem. 2019; 89: 881
- 102 Hassankhani A, Mosaddegh E. J. Appl. Chem. Res. 2019; 13: 89
- 103 Hassankhani A, Gholipour B, Rostamnia S. Polyhedron 2019; 175: 114217
- 104 Hassankhani A, Gholipour B, Rostamnia S, Zarenezhad E, Nouruzi N, Kavetskyy T, Khalilov R, Shokouhimehr M. Appl. Organomet. Chem. 2021; 35: e6346
- 105 Maleki A, Ravaghi P, Aghaei M, Movahed H. Res. Chem. Intermed. 2017; 43: 5485
- 106 Maleki A, Niksefat M, Rahimi J, Azadegan S. Polyhedron 2019; 167: 103
- 107 Gein VL, Prudnikova AN, Kurbatova AA, Dmitriev MV. Russ. J. Org. Chem. 2020; 56: 395
- 108 Suwito H, Kurnyawaty N, Haq KU, Abdulloh A, Indriani I. Molbank 2018; 2018: M998
- 109 Suwito H, Kurnyawaty N, Haq KU, Ramadhan R, Abdulloh A, Hardiyanti HD, Phuwapraisirisan P. Rasayan J. Chem. 2023; 16: 147
- 110 Tkachenko IG, Komykhov SA, Musatov VI, Shishkina SV, Dyakonenko VV, Shvets VN, Diachkov MV, Chebanov VA, Desenko SM. Beilstein J. Org. Chem. 2019; 15: 2390
- 111 Akbas E, Celik S, Ergan E, Levent A. J. Chem. Sci. 2019; 131: 30
- 112 Kour P, Singh VP, Khajuria B, Singh T, Kumar A. Tetrahedron Lett. 2017; 58: 4179
- 113 Karimi F, Tighsazzadeh B, Asadi B, Mohammadpoor-Baltork I, Layeghi M, Mirkhani V, Tangestaninejad S, Moghadam M. RSC Adv. 2022; 12: 22180
- 114 Datta K, Mitra B, Shil Sharma B, Ghosh P. ChemistrySelect 2022; 7: e202103602
- 115 Gein VL, Zamaraeva TM, Dmitriev MV, Ovchinnikova IG, Fedorova OV. Russ. J. Org. Chem. 2017; 53: 1090
- 116 Filatova ES, Fedorova OV, Slepukhin PA, Rusinov GL, Charushin VN. Chem. Heterocycl. Compd. 2018; 54: 971
- 117 Maleki A, Aghaei M, Kari T. Polycyclic Aromat. Compd. 2019; 39: 266
- 118 Ghorbani-Vaghei R, Shahriari A, Mahmoodi J, Maghbooli Y. Mol. Diversity 2017; 21: 865
- 119 Haleel AK, Mahendiran D, Rafi UM, Veena V, Shobana S, Rahiman AK. Inorg. Nano-Metal Chem. 2018; 48: 569
- 120 Shekarlab N, Ghorbani-Vaghei R, Alavinia S. J. Organomet. Chem. 2021; 949: 121971
- 121 Ahmed EA, Khodairy A, El-Remaily MA. E. A. A. A, Ahmed AM. Curr. Org. Chem. 2022; 26: 2214
- 122 Radwan MA. A, Alminderej FM, Awad HM. Molecules 2020; 25: 255
- 123 Abdollahi-Basir MH, Mirhosseini-Eshkevari B, Zamani F, Ghasemzadeh MA. Sci. Rep. 2021; 11: 5109
- 124 Wu L, Liu Y, Li Y. Molecules 2018; 23: 2330
- 125 Mekheimer RA, Abuo-Rahma GE.-D. A, Abd-Elmonem M, Yahia R, Hisham M, Hayallah AM, Mostafa SM, Abo-Elsoud FA, Sadek KU. J. Mol. Struct. 2022; 1267: 133615