Abstract
The molecules possessing triazine and tetrazine moieties belong to a special class of heterocyclic compounds. Both triazines and tetrazines are building blocks and have provided a new dimension to the design of biologically important organic molecules. Several of their derivatives with fine-tuned electronic properties have been identified as multifunctional, adaptable, switchable, remarkably antifungal, anticancer, antiviral, antitumor, cardiotonic, anti-HIV, analgesic, anti-protozoal, etc. The objective of this review is to comprehensively describe the recent developments in synthesis, coordination properties, and various applications of triazine and tetrazine molecules. The rich literature demonstrates various synthetic routes for a variety of triazines and tetrazines through microwave-assisted, solid-phase, metal-based, [4+2] cycloaddition, and multicomponent one-pot reactions. Synthetic approaches contain linear, angular, and fused triazine and tetrazine heterocycles through a combinatorial method. Notably, the triazines and tetrazines undergo a variety of organic transformations, including electrophilic addition, coupling, nucleophilic displacement, and intramolecular cyclization. The mechanistic aspects of these heterocycles are discussed in a detailed way. The bioorthogonal application of these polyazines with various strained alkenes and alkynes provides a new prospect for investigations in chemical biology. This review systematically encapsulates the recent developments and challenges in the synthesis and possible potential applications of various triazine and tetrazine systems.
Graphical Abstract
Similar content being viewed by others
Abbreviations
- THF:
-
Tetrahydrofuran
- MeOH:
-
Methanol
- Pd(OAc)2 :
-
Palladium (II) acetate
- DMSO :
-
Dimethyl sulfoxide
- DMF :
-
N,N-Dimethylformamide
- CuI :
-
Cuprous iodide
- Cu(OAc)2 :
-
Copper acetate
- p-TsOH :
-
para-Toluenesulfonic aicd
- DBU :
-
1,8-Diazabicyclo(5.4.0)undec-7-ene
- DDQ :
-
2,3-Dichloro-5-6-dicyano-1,4-benzoquinone
- CF3SO3H :
-
Trifluoromethanesulfonic acid
- MeCN :
-
Acetonitrile
- CC :
-
Cyanuric chloride
- TPP :
-
Tetraphenylporphyrin
- Tf2O :
-
Triflic anhydride
- TEA :
-
Triethylamine
- TBAI :
-
Tetrabutylammonium iodide
- t-BuOK :
-
Potassium tert-butoxide
- t-BuOH :
-
tert-Butyl-alcohol
- EtOH :
-
Ethanol
- NMP :
-
N-Methyl-2-pyrrolidone
- IBX :
-
2-Iodoxybenzoic acid
- OMS-2 :
-
Manganese oxide octahedral molecular sieve
- DMAP :
-
4-Dimethyl-aminopyridine
- EDA :
-
Ethylenediamine
- TFA :
-
Trifluoroacetic acid
- iPrBr :
-
Isopropylbromide
- Et2O :
-
Diethylether
- mCPBA :
-
m-Chloroperoxybenzoic acid
- EtOAc :
-
Ethylacetate
- DCM :
-
Dichloromethane
- SNAr :
-
Nucleophilic aromatic substitution
- DPPA :
-
Diphenylphosphoryl azide
- PIDA:
-
Poly(diiododiacetylene)
- LLCT :
-
Ligand–ligand charge transfer
- ICT :
-
Intramolecular charge transfer
- TTF :
-
Tetrathiafulvalene
- MLCT :
-
Metal–ligand charge transfer
- TTCs :
-
Thiophenyl triazine
- TICT :
-
Twisted intramolecular charge transfer
- MCTP :
-
Microporous covalent triazine-based polymer
- ER :
-
Electrorheological property
- BOTZ :
-
Bis-opened triazine
- DSC :
-
Differential scanning calorimetry
- Td :
-
Thermal decomposition
- TCO :
-
trans-Cyclooctene
- CDI :
-
1,1′-Carbonyldiimidazole
References
Elattar KM, Mert BD, Monier M, El-Mekabaty A (2020) RSC Adv 10:15461–15492
Prachayasittikul S, Pingaew R, Worachartcheewan A, Sinthupoom N, Prachayasittikul V, Ruchirawat S, Prachayasittikul V (2016) Mini-Rev Med Chem 17:869–901
Xu Y, Hao SY, Zhang XJ, Li WB, Qiao XP, Wang ZX, Chen SW (2020) Bioorg Med Chem Lett 30:126885
Cascioferro S, Parrino B, Carbone D, Schillaci D, Giovannetti E, Cirrincione G, Diana P (2020) J Med Chem 63:7923–7956
Ali SH, Sayed AR (2021) Synth Commun 51:670–700
Xie XX, Li H, Wang J, Mao S, Xin MH, Lu SM, Mei QB, Zhang SQ (2015) Bioorg Med Chem 23:6477–6485
Omar AM, Bajorath J, Ihmaid S, Mohamed HM, El-Agrody AM, Mora A, El-Araby ME, Ahmed HEA (2020) Bioorg Chem 101:103992
Muthukrishnan I, Sridharan V, Menéndez JC (2019) Chem Rev 119:5057–5191
Shen M, Zhao J, Xu Y, Zhang X, Fan X (2021) J Org Chem 86:15203–15216
Wang Z, Fei Y, Tang C, Cui L, Shen J, Yin K, Lu S, Li J (2021) Org Lett 23:4094–4098
Totobenazara J, Burke AJ (2015) Tetrahedron Lett 56:2853–2859
Nemallapudi BR, Guda DR, Ummadi N, Avula B, Zyryanov GV, Reddy CS, Gundala S (2021) Polycycl Aromat Compd 20:1–19
Dheer D, Singh V, Shankar R (2017) Bioorg Chem 71:30–54
Neochoritis CG, Zhao T, Dömling A (2019) Chem Rev 119:1970–2042
Dhiman N, Kaur K, Jaitak V (2020) Bioorg Med Chem 28:115599
Sarvary A, Maleki A (2015) Mol Divers 19:189–212
Mykhailiuk PK (2021) Chem Rev 121:1670–1715
Ansari A, Ali A, AsifShamsuzzaman M (2017) New J Chem 41:16–41
Reddy MM, Sivaramakrishna A (2020) Chem Sel 5:4816–4821
Reddy MM, Sivaramakrishna A (2020) J Heterocycl Chem 57:942–954
Reddy MM, Sivaramakrishna A (2021) Synth Commun 51:103–113
Sadimenko AP, Okoh OO (2019) Organometallic complexes of polyazines, vol 127, 1st edn. Elsevier Inc, New York, pp 315–390
Liu M, Guo L, Jin S, Tan B (2019) J Mater Chem A 7:5153
Kuhn P, Antonietti M, Thomas A (2008) Angew Chem Int Ed 47:3450–3453
Diercks CS, Yaghi OM (2017) Science 355:6328
Xu Y, Jin S, Xu H, Nagai A, Jiang D (2013) Chem Soc Rev 42:8012–8031
Liu J, Zan W, Li K, Yang Y, Bu F, Xu Y (2017) J Am Chem Soc 139:11666–11669
Liu M, Huang Q, Wang S, Li Z, Li B, Jin S, Tan B (2018) Angew Chem Int Ed 57:11968–11972
Yu SY, Mahmood J, Noh HJ, Seo JM, Jung SM, Shin SH, Im YK, Jeon IY, Baek JB (2018) Angew Chem Int Ed 57:8438–8442
Wang Li, Zhang J, Zhao J, Ping Yu, Wang S, Hongmei Hu, Wang R (2020) Catal Rev 62:524–565
Kolb HC, Finn MG, Sharpless KB (2001) Angew Chem Int Ed 40:2004–2021
Sletten EM, Bertozzi CR (2011) Acc Chem Res 44:666–676
Patterson DM, Prescher JA (2015) Curr Opin Chem Biol 28:141–149
Devaraj NK, Weissleder R (2011) Acc Chem Res 44:816–827
Li J, Chen PR (2016) Nat Publ Gr 12:129–137
Boutureira O, Bernardes GJL (2015) Chem Rev 115:2174–2195
Mix KA, Aronoff MR, Raines RT (2016) ACS Chem Biol 11:3233–3244
Tornøe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057–3064
Knall AC, Slugovc C (2013) Chem Soc Rev 42:5131–5142
Oliveira BL, Guo Z, Bernardes GJL (2017) Chem Soc Rev 46:4895–4950
Hang HC, Wilson JP, Charron G (2011) Acc Chem Res 44:699–708
Boger DL (1986) Chem Rev 86:781–793
Tolshchina SG, Rusinov GL, Charushin VN (2013) Chem Heterocycl Compd 49:66–91
Kaim W (2002) Coord Chem Rev 230:127–139
Saracoglu N (2007) Tetrahedron 63:4199–4236
Clavier G, Audebert P (2010) Chem Rev 110:3299–3314
Puthiaraj P, Lee Y-R, Zhang S, Ahn W-S (2016) J Mater Chem A 4:16288–16311
Palkovits R, Antonietti M, Kuhn P, Thomas A, Schüth F (2009) Angew Chemie Int Ed 48:6909–6912
Artz J, Mallmann S, Palkovits R (2015) Chemsuschem 8:672–679
Zhang B, Wei M, Mao H, Pei X, Alshmimri SA, Reimer JA, Yaghi OM (2018) J Am Chem Soc 140:12715–12719
Zhu G, Shi S, Liu M, Zhao L, Wang M, Zheng X, Gao J, Xu J (2018) ACS Appl Mater Interfaces 10:12612–12617
Bi J, Fang W, Li L, Wang J, Liang S, He Y, Liu M, Wu L (2015) Macromol Rapid Commun 36:1799–1805
Guo L, Niu Y, Xu H, Li Q, Razzaque S, Huang Q, Jin S, Tan B (2018) J Mater Chem A 6:19775–19781
Xie J, Shevlin SA, Ruan Q, Moniz SJA, Liu Y, Liu X, Li Y, Lau CC, Guo ZX, Tang J (2018) Energy Environ Sci 11:1617–1624
Zhu X, Tian C, Mahurin SM, Chai SH, Wang C, Brown S, Veith GM, Luo H, Liu H, Dai S (2012) J Am Chem Soc 134:10478–10484
Liebl MR, Senker J (2013) Chem Mater 25:970–980
Zhao Y, Yao KX, Teng B, Zhang T, Han Y (2013) Energy Environ Sci 6:3684–3692
Hug S, Stegbauer L, Oh H, Hirscher M, Lotsch BV (2015) Chem Mater 27:8001–8010
Yu W, Gu S, Fu Y, Xiong S, Pan C, Liu Y, Yu G (2018) J Catal 362:1–9
Hao L, Ning J, Luo B, Wang B, Zhang Y, Tang Z, Yang J, Thomas A, Zhi L (2015) J Am Chem Soc 137:219–225
Xu F, Yang S, Jiang G, Ye Q, Wei B, Wang H (2017) ACS Appl Mater Interfaces 9:37731–37738
Talapaneni SN, Hwang TH, Je SH, Buyukcakir O, Choi JW, Coskun A (2016) Angew Chem Int Ed 55:3106–3111
Li Y, Zheng S, Liu X, Li P, Sun L, Yang R, Wang S, Wu ZS, Bao X, Deng WQ (2017) Angew Chem Int Ed 56:1–6
Liu J, Lyu P, Zhang Y, Nachtigall P, Xu Y (2018) Adv Mater 30:1705401
Sharma A, Sheyi R, De Torre BG, El-faham A, Albericio F (2021) Molecules 26:864
Hashem HE (2021) Mini-Rev Org Chem 18:1127–1133
Bernat Z, Szymanowska A, Kciuk M, Kotwica-Mojzych K, Mojzych M (2020) Molecules 25:1–20
Sreeperumbuduru RS, Abid ZM, Claunch KM, Chen HH, McGillivray SM, Simanek EE (2016) RSC Adv 6:8806–8810
Bhat HR, Singh UP, Gahtori P, Ghosh SK, Gogoi K, Prakash A, Singh RK (2013) New J Chem 37:2654–2662
Bhat HR, Masih A, Shakya A, Ghosh SK, Singh UP (2020) J Heterocycl Chem 57:390–399
Mogilski S, Kubacka M, Łażewska D, Więcek M, Głuch-Lutwin M, Tyszka-Czochara M, Bukowska-Strakova K, Filipek B, Kieć-Kononowicz K (2017) Inflamm Res 66:79–95
Shanmugam M, Narayanan K, Hari Prasad KH, Karthikeyan D, Chandrasekaran L, Atchudan R, Chidambaranathan V (2018) New J Chem 42:1698–1714
Zvarych V, Stasevych M, Novikov V, Rusanov E, Vovk M, Szweda P, Grecka K, Milewski S (2019) Molecules 24:1–20
Congreve M, Andrews SP, Doré AS, Hollenstein K, Hurrell E, Langmead CJ, Mason JS, Ng IW, Tehan B, Zhukov A, Weir M, Marshall FH (2012) J Med Chem 55:1898–1903
Bernat Z, Szymanowska A, Kciuk M, Kotwica-Mojzych K, Mojzych M (2020) Molecules 25:3948
Törk L, Jiménez-Osés G, Doubleday C, Liu F, Houk KN (2015) J Am Chem Soc 137:4749–4758
Bagge RE, Mauldin TC, Boday DJ, Kobilka BM, Loy DA (2017) Chem Mater 29:7953–7960
Wu H, Yang J, Šečkute J, Devaraj NK (2014) Angew Chem Int Ed 53:5805–5809
Denk C, Svatunek D, Mairinger S, Stanek J, Filip T, Matscheko D, Kuntner C, Wanek T, Mikula H (2016) Bioconjug Chem 27:1707–1712
Lipunova GN, Nosova EV, Zyryanov GV, Charushin VN, Chupakhin ON (2021) Org Chem Front 8:5182
Chen H, Dao P, Laporte A, Garbay C (2010) Tetrahedron Lett 51:3174–3176
Dao P, Garbay C, Chen H (2012) Tetrahedron 68:3856–3860
Kalinina SA, Kalinin DV, Dolzhenko AV (2013) Tetrahedron Lett 54:5537–5540
Lim FPL, Luna G, Dolzhenko AV (2015) Tetrahedron Lett 56:7016–7019
Debnath P, Majumdar KC (2014) Tetrahedron Lett 55:6976–6978
Xu X, Zhang M, Jiang H, Zheng J, Li Y (2014) Org Lett 16:3540–3543
Huang H, Guo W, Wu W, Li CJ, Jiang H (2015) Org Lett 17:2894–2897
Habibi D, Vakili S (2015) Chin J Catal 36:620–625
Meng J, Wen M, Zhang S, Pan P, Yu X, Deng WP (2017) J Org Chem 82:1676–1687
Padalkar VS, Patil VS, Phatangare KR, Gupta VD, Umape PG, Sekar N (2010) Mater Sci Eng B Solid-State Mater Adv Technol 170:77–87
Idzik KR, Rapta P, Cywinski PJ, Beckert R, Dunsch L (2010) Electrochim Acta 55:4858–4864
Thirumurugan P, Perumal PT (2011) Dyes Pigm 88:403–412
Üngören ŞH, Dilekoǧlu E, Koca I (2013) Chin Chem Lett 24:1130–1133
Kothayer H, Elshanawani AA, Abu Kull ME, El-Sabbagh OI, Shekhar MPV, Brancale A, Jones AT, Westwell AD (2013) Bioorg Med Chem Lett 23:6886–6889
Dao P, Garbay C, Chen H (2013) Tetrahedron 69:3867–3871
Herrera A, Riaño A, Moreno R, Caso B, Pardo ZD, Fernández I, Sáez E, Molero D, Sánchez-Vázquez A, Martínez-Alvarez R (2014) J Org Chem 79:7012–7024
Sureshbabu VV, Vishwanatha TM, Vasantha B (2010) Synlett 25:1037–1042
Krishnamurthy M, Basavaprabhu K, Sharanabai M, Sureshbabu VV (2014) Tetrahedron Lett 55:5609–5612
Korovin AV, Tkachev AV (2001) Bull Acad Sci USSR Div Chem Sci 50:304–310
Dinh Ngoc T, Moons N, Kim Y, De Borggraeve W, Mashentseva A, Andrei G, Snoeck R, Balzarini J, Dehaen W (2014) Bioorg Med Chem 22:3292–3300
Lauria A, Alfio A, Bonsignore R, Gentile C, Martorana A, Gennaro G, Barone G, Terenzi A, Almerico AM (2014) Bioorg Med Chem Lett 24:3291–3297
Lewis FW, Harwood LM, Hudson MJ, Drew MGB, Desreux JF, Vidick G, Bouslimani N, Modolo G, Wilden A, Sypula M, Vu TH, Simonin JP (2011) J Am Chem Soc 133:13093–13102
Klenc J, Raux E, Barnes S, Sullivan S, Duszynska B, Bojarski AJ, Strekowski L (2015) J Heterocycl Chem 46:1259–1265
You Q, Wang F, Wu C, Shi T, Min D, Chen H, Zhang W (2015) Org Biomol Chem 13:6723–6727
Wang G, Wang J, He D, Li X, Li J, Peng Z (2016) Bioorg Med Chem Lett 26:2806–2809
Yavari I, Mosaferi S (2017) Monatshefte Chem 148:963–966
Liu Y, Guo X, Tang D, Wang J, Wu P, Han J, Chen B (2017) Chin J Chem 35:1222–1226
Shabunina OV, Starnovskaya ES, Shtaits YK, Kopchuk DS, Kovalev IS, Zyryanov GV, Rusinov VL, Chupakhin ON (2018) Russ J Org Chem 54:1576–1578
Sugimura H, Takeuchi R, Ichikawa S, Nagayama E, Sasaki I (2018) Org Lett 20:3434–3437
Zhang Y, Liu Y, Zhang J, Gu R, Han S (2019) Tetrahedron Lett 60:151289
Shen J, Meng X (2019) Catal Commun 127:58–63
Marzi M, Pourshamsian K, Hatamjafari F, Shiroudi A, Oliaey AR (2019) Russ J Bioorg Chem 45:391–397
Karci F (2005) Color Technol 121:275–280
Yıldırım F, Demirçalı A, Kiraz AÖ, Karcı F (2020) J Mol Struct 1222:128850
Shokoohian M, Hazeri N, Maghsoodlou M, Lashkari M (2019) Chem J Mold 14:97–104
Shokoohian M, Hazeri N, Maghsoodlou MT, Lashkari M (2020) Polycycl Aromat Compd 20:1–12
El-Reedy AAM, Soliman NK (2020) Sci Rep 10:1–18
Li F, Wang C, Xu Y, Zhao Z, Su J, Luo C, Ning Y, Li Z, Li C, Wang L (2021) Mol Catal 505:111519
Shabunina OV, Shtaitz YK, Kopchuk DS, Krinochkin AP, Santra S, Zyryanov GV, Wang Z, Rusinov VL, Chupakhin ON (2021) Chem Heterocycl Compd 57:462–466
Guo W, Xie Z, Cai L, Liu G, Deng L, Mei W, Zou X, Zhong Y, Zhuo X, Zheng L, Fan X (2021) J Org Chem 86:8365–8380
Ibrahim HM, Behbehani H (2021) ACS Omega 6:16086–16099
Liu Y, Qi X, Zhang W, Yin P, Cai Z, Zhang Q (2021) Org Lett 23:734–738
Gao Y, Lam Y (2010) J Comb Chem 12:69–74
Karver MR, Weissleder R, Hilderbrand SA (2011) Bioconjug Chem 22:2263–2270
Rao GW, Guo YM, Hu WX (2012) ChemMedChem 7:973–976
Xu F, Yang ZZ, Jiang JR, Ke ZL (2012) J Chem Crystallogr 42:600–605
Liu H, Wei Y (2013) Tetrahedron Lett 54:4645–4648
Benson CR, Hui AK, Parimal K, Cook BJ, Chen CH, Lord RL, Flood AH, Caulton KG (2014) Dalt Trans 43:6513–6524
Li C, Ge H, Yin B, She M, Liu P, Li X, Li J (2015) RSC Adv 5:12277–12286
Chavez DE, Bottaro JC, Petrie M, Parrish DA (2015) Angew Chem Int Ed 54:12973–12975
Zhao HW, Pang HL, Li B, Tian T, Chen XQ, Song XQ, Meng W, Yang Z, Liu YY, Di Zhao Y (2016) RSC Adv 6:25562–25567
Sadchikova EV (2016) Russ Chem Bull 65:1867–1872
Klenov MS, Guskov AA, Anikin OV, Churakov AM, Strelenko YA, Fedyanin IV, Lyssenko KA, Tartakovsky VA (2016) Angew Chem Int Ed 55:11472–11475
Fang Z, Hu WL, Liu DY, Yu CY, Hu XG (2017) Green Chem 19:1299–1302
Mao W, Shi W, Li J, Su D, Wang X, Zhang L, Pan L, Wu X, Wu H (2019) Angew Chem Int Ed 58:1106–1109
Qu Y, Sauvage F-X, Clavier G, Miomandre F, Audebert P (2018) Angew Chem Int Ed 57:12057–12061
Xu X, Zhang K, Li P, Yao H, Lin A (2018) Org Lett 20:1781–1784
Wu ZC, Boger DL (2019) J Am Chem Soc 141:16388–16397
Meinecke J, Koert U (2019) Org Lett 21:7609–7612
Xie Y, Fang Y, Huang Z, Tallon AM, Ende CW, Fox JM (2020) Angew Chem Int Ed 59:16967–16973
Ros E, Bellido M, Verdaguer X, De Pouplana LR, Riera A (2020) Bioconjug Chem 31:933–938
Cui X, Ding C, Zhang C, Jiao Z, Zhang L, Zhao X, Zhao L (2021) J Phys Chem A 125:4715–4726
Yang J, Karver MR, Li W, Sahu S, Devaraj NK (2012) Angew Chem Int Ed 51:5222–5225
Wu H, Devaraj NK (2018) Acc Chem Res 51:1249–1259
Choi SK, Kim J, Kim E (2021) Molecules 26:1–16
Sun H, Xue Q, Zhang C, Wu H, Feng P (2022) Org Chem Front 9:481–498
Wang L, Zhang J, Zhao J, Yu P, Wang S, Hu H, Wang R (2020) Catal Rev Sci Eng 62:524–565
Zhang HX, Kato M, Sasaki Y, Ohba T, Ito H, Kobayashi A, Chang HC, Uosaki K (2012) Dalt Trans 41:11497–11506
Zhang L, Zou L, Xiao J, Zhou P, Zhong C, Chen X, Qin J, Mariz IFA, MaçÔas E (2012) J Mater Chem 22:16781–16790
Branowska D, Chaciak B, Siuchta O, Olender E, Ledwon P, Lapkowski M, Poronik E, Wysocki W, Karczmarzyk Z, Skora L, Filapek M, Krompiec S, Urbanczyk-Lipkowska Z, Kalicki P (2013) New J Chem 37:1982–1988
Pop F, Riobé F, Seifert S, Cauchy T, Ding J, Dupont N, Hauser A, Koch M, Avarvari N (2013) Inorg Chem 52:5023–5034
Cai Z, Zhou M, Li B, Chen Y, Jin F, Huang J (2014) New J Chem 38:3042–3049
Laramée-Milette B, Lussier F, Ciofini I, Hanan GS (2015) Dalt Trans 44:11551–11561
Zhu Z, Shao E, Xu S, Sun H, Zhang G, Xie Z, Zhang W, Gao Z (2016) RSC Adv 6:76883–76889
Pradhan B, Pathak SK, Gupta RK, Gupta M, Pal SK, Achalkumar AS (2016) J Mater Chem C 4:6117–6130
Lee MM, Lin JL, Chang CW, Hung CY, Chen CW, Hsu CP, Sun SS (2017) Eur J Inorg Chem 2017:5224–5237
Das P, Kumar A, Chowdhury A, Mukherjee PS (2018) ACS Omega 3:13757–13771
Kato SI, Jin S, Kimura T, Yoshikawa N, Nara D, Imamura K, Shiota Y, Yoshizawa K, Katoono R, Yamanobe T, Uehara H, Nakamura Y (2018) Org Biomol Chem 16:3584–3595
Tang Y, Imler GH, Parrish DA, Shreeve JM, Appl ACS (2019) Energy Mater 2:8871–8877
Su H, Zhu S, Qu M, Liu R, Song G, Zhu H (2019) J Phys Chem C 123:15685–15692
Xiao Y, Li B, You ZX, Xing YH, Bai FY, Sun LX, Shi Z (2021) J Mater Chem C 9:3193–3203
Muniyasamy H, Chinnadurai C, Nelson M, Veeramanoharan A, Sepperumal M, Ayyanar S (2021) Ind Eng Chem Res 60:7987–7997
Bhanja P, Chatterjee S, Bhaumik A (2016) ChemCatChem 8:3089–3098
Abdurashid A, Ahat B, Mirzehmet A, Awut T, Nurulla I (2016) J Polym Res 23:1–9
Zhang G, Zheng H, Guo M, Du L, Liu G, Liu J (2016) J Wood Sci 62:526–536
Dong YZ, Kwon SH, Choi HJ, Puthiaraj P, Ahn WS (2018) Colloid Polym Sci 296:907–915
Zhang A, Wu H, Fu H, Xu Z, Ji Y (2019) J Chem Eng Data 64:1529–1537
Zuo H, Guo Y, Zhao W, Hu K, Wang XY, He L, Zhang S (2019) ACS Appl Mater Interfaces 11:46149–46156
Biswas T, Halder A, Paliwal KS, Mitra A, Tudu G, Banerjee R, Mahalingam V (2020) Chem Asian J 15:1683–1687
Guo J, Wang L, Huang J (2020) Ind Eng Chem Res 59:3205–3212
Yue C, Wang W, Li F (2020) Chemsuschem 13:5996–6004
Xu C, Xie Q, Zhang W, Xiong S, Pan C, Tang J, Yu G (2020) Macromol Rapid Commun 41:1–6
Zhuang Y, Shan H, Zhang Z, Li S, Zhu Q, Si Z, Yang S, Yang Z, Cai D, Qin P (2021) Dyes Pigm 192:109421
Peng X, Zhang J, Stachurski ZH, Banaszak Holl MM, Xiao P (2021) ACS Appl Mater Interfaces 13:46033–46042
Raza AA, Ravi S, Tajudeen SS, Sheriff AKI (2021) React Funct Polym 167:105011
Bhunia A, Esquivel D, Dey S, Fernández-Terán R, Goto Y, Inagaki S, Van Der Voort P, Janiak C (2016) J Mater Chem A 4:13450–13457
Guichen Y, Yin M, Zhu J, Zhou H, Miao Y, Huang J, Wang H, Su J (2021) Tetrahedron 90:132175
Yan Z, Lu T, Liu Y, Liu W, Zhao B, Wang Y, Ge Z (2021) ACS Omega 6:18591–18597
Qi Y, Weng Z, Kou Y, Song L, Li J, Wang J, Zhang S, Liu C, Jian X (2021) Chem Eng J 406:1385–8947
Ananthnag GS, Mague JT, Balakrishna MS (2015) Inorg Chem 54:10985–10992
Gopi S, Kathiresan M (2017) Polymer (Guildf) 109:315–320
Bavykina AV, Olivos-Suarez AI, Osadchii D, Valecha R, Franz R, Makkee M, Kapteijn F, Gascon J, Appl ACS (2017) Mater Interfaces 9:26060–26065
Bavykina AV, Mautscke HH, Makkee M, Kapteijn F, Gascon J, LlabrésiXamena FX (2017) CrystEngComm 19:4166–4170
Artz J, Delidovich I, Pilaski M, Niemeier J, Kübber BM, Rahimi K, Palkovits R (2018) RSC Adv 8:22392–22401
Bohra H, Li P, Yang C, Zhao Y, Wang M (2018) Polym Chem 9:1972–1982
Mobinikhaledi A, Moghanian H, Ajerloo B, Dousti F (2020) Appl Organomet Chem 34:1–10
Tahir N, Wang G, Onyshchenko I, De Geyter N, Leus K, Morent R, Van Der Voort P (2019) J Catal 375:242–248
Elavarasan S, Kala K, Muhammad I, Bhaumik A, Sasidharan M (2019) Mol Catal 476:110521
Das SK, KrishnaChandra B, Molla RA, Sengupta M, Islam SM, Majee A, Bhaumik A (2020) Mol Catal 480:110650
Granifo J (1995) Polyhedron 14:1593–1599
Granifo J (1995) Polyhedron 15:203–209
Granifo J (1999) Polyhedron 18:1061–1066
Rezaei B, Mokhtarianpour M, Ensafi AA, Hadadzadeh H, Shakeri J (2015) Polyhedron 101:160–164
Buck DM, Kunz D (2015) Organometallics 34:5335–5340
Celik D, Kose M (2019) Appl Organomet Chem 33:1–12
Singh S (2018) ChemistrySelect 3:6786–6790
Berdiell IC, Kulak AN, Warriner SL, Halcrow MA (2018) ACS Omega 3:18466–18474
Kozhevnikov VN, Deary ME, Mantso T, Panayiotidis MI, Sims MT (2019) Chem Commun 55:14283–14286
Schäfer T, Sedykh AE, Becker J, Müller-Buschbaum K (2020) Z Anorg Allg Chem 646:1555–1562
Pal P, Das K, Hossain A, Gomila RM, Frontera A, Mukhopadhyay S (2021) New J Chem 45:11689–11696
Bass R, Jenkinson S, Wright J, Smulders-Srinivasan T, Marshall JC, Castagnolo D (2017) ChemMedChem 12:288–291
Junaid A, Lim FPL, Tiekink ERT, Dolzhenko AV (2020) RSC Adv 10:25517–25528
Singh UP, Pathak M, Dubey V, Bhat HR, Gahtori P, Singh RK (2012) Chem Biol Drug Des 80:572–583
Srivastava JK, Dubey P, Singh S, Bhat HR, Kumawat MK, Singh UP (2015) RSC Adv 5:14095–14102
Patel MB, Harikrishnan U, Valand NN, Mehta DS, Joshi KV, Kumar SP, Chikhalia KH, George LB, Jasrai YT, Menon SK (2013) RSC Adv 3:8734–8746
Bhat HR, Singh UP, Gahtori P, Ghosh SK, Gogoi K, Prakash A, Singh RK (2013) RSC Adv 3:2942–2952
Almalioti F, MacDougall J, Hughes S, Hasson MM, Jenkins RL, Ward BD, Tizzard GJ, Coles SJ, Williams DW, Bamford S, Fallis IA, Dervisi A (2013) Dalt Trans 42:12370–12380
Amir M, Ali I, Hassan MZ, Mulakayala N (2014) Arch Pharm (Weinheim) 347:958–968
Khan AA, Siddiqui N, Akhtar MJ, Ali Z, Yar MS (2016) Arch Pharm Chem Life Sci 349:277–292
Lourens ACU, Gravestock D, Van Zyl RL, Hoppe HC, Kolesnikova N, Taweechai S, Yuthavong Y, Kamchonwongpaisan S, Rousseau AL (2016) Org Biomol Chem 14:7899–7911
Malinge J, Allain C, Galmiche L, Miomandre F, Audebert P (2011) Chem Mater 23:4599–4605
Nazarenko I, Pop F, Sun Q, Hauser A, Lloret F, Julve M, El-Ghayoury A, Avarvari N (2015) Dalton Trans 44:8855–8866
Allain C, Piard J, Brosseau A, Han M, Paquier J, Marchandier T, Lequeux M, Boissière C, Audebert P, Appl ACS (2016) Mater Interfaces 8:19843–19846
Rouschmeyer P, Guillou N, Serre C, Clavier G, Martineau C, Audebert P, Elkaïm E, Allain C, Devic T (2017) Inorg Chem 56:8423–8429
Steparuk AS, Tolshchina SG, Kazin NA, Irgashev RA, Zhilina EF, Aleksandrov AE, Tameev AR, Rusinov GL (2021) Russ Chem Bull 70:1109–1117
Moral M, Garzón A, García G, Granadino-Roldán JM, Fernández-Gómez M (2015) J Phys Chem C 119:4588–4599
Pluczyk S, Zassowski P, Quinton C, Audebert P, Alain-Rizzo V, Lapkowski M (2016) J Phys Chem C 120:4382–4391
Guerret-Legras L, Audebert P, Audibert JF, Niebel C, Jarrosson T, Serein-Spirau F, Lère-Porte JP (2019) J Electroanal Chem 840:60–66
Kardelis V, Denk MM, Adronov A (2021) Angew Chem Int Ed 60:2980–2986
Tang Y, Kumar D, Shreeve JM (2017) J Am Chem Soc 139:13684–13687
Liu Q, Yang B, Yang J, Ren Y, Zhang X, Ma H, Xu K, Zhao F, Hu R (2017) J Coord Chem 70:2249–2260
Chen X, Zeng T, Zhang C, Guo Z, Li S, Mai T, Gao R, Ma H (2018) Chem Res Chin Univ 34:959–964
Chen X, Zhang C, Bai Y, Guo Z, Yao Y, Song J, Ma H (2018) Acta Crystallogr Sect C Struct Chem 74:666–672
Samanta S, Das S, Biswas P (2013) J Org Chem 78:11184–11193
Samanta S, Biswas P (2015) RSC Adv 5:84328–84333
Das S, Samanta S, Ray S, Biswas P (2015) RSC Adv 5:75263–75267
Le T, Courant T, Merad J, Allain C, Audebert P, Masson G (2019) J Org Chem 84:16139–16146
An WK, Zheng SJ, Zhang HX, Shang TT, Wang HR, Xu XJ, Jin Q, Qin Y, Ren Y, Jiang S, Xu CL, Hou MS, Pan Z (2021) Green Chem 23:1292–1299
Bach M, Roy S, Sarkar B, Bubrin M, Niemeyer M, Fiedler J, Duboc C, Kaim W (2015) Z Anorg Allg Chem 641:327–331
Saghatforoush L, Khoshtarkib Z, Amani V, Bakhtiari A (2016) J Solid State Chem 233:311–319
Saghatforoush L, Moeini K, Golsanamlou V, Amani V, Bakhtiari A (2018) Inorg Chim Acta 483:392–401
Stetsiuk O, Petrusenko SR, Sorace L, Lupan A, Attia AAA, Kokozay VN, El-Ghayoury A, Avarvari N (2019) Dalt Trans 48:11966–11977
Thomas JD, Cui H, North PJ, Hofer T, Rader C, Burke TR (2012) Bioconjug Chem 23:2007–2013
Machida T, Lang K, Xue L, Chin JW, Winssinger N (2015) Bioconjug Chem 26:802–806
Maggi A, Ruivo E, Fissers J, Vangestel C, Chatterjee S, Joossens J, Sobott F, Staelens S, Stroobants S, Van Der Veken P, Wyffels L, Augustyns K (2016) Org Biomol Chem 14:7544–7551
Davies S, Qiao L, Oliveira BL, Navo CD, Jiménez-Osés G, Bernardes GJL (2019) ChemBioChem 20:1541–1546
Acknowledgements
The authors thank VIT-SEED GRANT for the financial assistance to explore the novel chemistry of triazines and tetrazines. Mr. Joydip Mondal is grateful to VIT for the research fellowship.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors do not have any conflicts of interest to declare.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Mondal, J., Sivaramakrishna, A. Functionalized Triazines and Tetrazines: Synthesis and Applications. Top Curr Chem (Z) 380, 34 (2022). https://doi.org/10.1007/s41061-022-00385-7
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s41061-022-00385-7