Synlett 2024; 35(14): 1669-1697
DOI: 10.1055/s-0042-1751533
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Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

,
Disha D. Shah
,
Aayushi C. Shah
,
Tithi S. Shah
,
Tanvi M. Patel
,
Devalben K. Rana
,
Dipen K. Sureja
,
Kunjan B. Bodiwala


Abstract

The versatility of aza- and oxa-heterocyclic compounds has garnered significant attention in recent times. A large number of currently approved pharmaceutical products include nitrogen- and oxygen-containing heterocycles. Recent nanotechnological developments have propelled an upsurge in the applications of nanocatalysis for heterocyclic synthesis. Metal nanoparticles (MNPs) have emerged as promising catalysts for the synthesis of aza- and oxa-heterocycles owing to their unique physicochemical properties. Various MNPs including gold, silver, nickel and palladium have been evaluated for their catalytic activities in different reaction types, including cyclisation, coupling, hydrogenation and oxidative transformations. The MNPs have exhibited remarkable catalytic efficiency when utilised under optimal conditions. These catalysts have showcased high reusability and recyclability, yielding satisfactory amounts of the desired heterocyclic compound. The present work provides a detailed overview of recent advances in the area of MNP-assisted synthetic construction of aza- and oxa-heterocycles, published during the previous calendar year, 2022. The review serves as a valuable resource and also paves the way for future investigations in the development of novel catalytic strategies for heterocycle synthesis.

1 Introduction

2 Nanocatalysis

3 Aza- and Oxa-Heterocycle Synthesis Catalysed by MNPs

3.1 AuNPs

3.2 CuNPs

3.3 CoNPs

3.4 FeNPs

3.5 NiNPs

3.6 PdNPs

3.7 PtNPs

3.8 SiNPs

3.9 ZnNPs

3.10 Bimetallic NPs

3.11 Other MNPs

4 Summary and Outlook



Publikationsverlauf

Eingereicht: 21. Oktober 2023

Angenommen nach Revision: 07. November 2023

Artikel online veröffentlicht:
03. Januar 2024

© 2024. Thieme. All rights reserved

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Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Current address: Department of Pharmaceutical Chemistry and Quality Assurance, Institute of Pharmacy, Nirma University, Ahmedabad 382 481, Gujarat, India.
  • 2 Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
  • 3 Shalmali N, Ali MR, Bawa S. Mini-Rev. Med. Chem. 2018; 18: 142
  • 4 Saha R, Tanwar O, Marella A, Alam MM, Akhter M. Mini-Rev. Med. Chem. 2013; 13: 1027
  • 5 Alvarez-Builla J, Vaquero JJ, Barluenga J. Modern Heterocyclic Chemistry, Vol. 1. Alvarez-Builla J, Vaquero JJ, Barluenga J. Wiley-VCH Verlag GmbH; Weinheim: 2011
    • 6a Neto JS. S, Zeni G. Coord. Chem. Rev. 2020; 409: 213217
    • 6b Neto JS. S, Zeni G. Org. Chem. Front. 2019; 7: 155
  • 7 Cortes-Clerget M, Yu J, Kincaid JR. A, Walde P, Gallou F, Lipshutz BH. Chem. Sci. 2021; 12: 4237
  • 8 Chng LL, Erathodiyil N, Ying JY. Acc. Chem. Res. 2013; 46: 1825
  • 9 Reddy PN, Padmaja P, Subba Reddy BV, Rambabu G. RSC Adv. 2015; 5: 51035
  • 10 Gallou F, Isley NA, Ganic A, Onken U, Parmentier M. Green Chem. 2016; 18: 14
  • 11 Lassaletta JM. Nat. Commun. 2020; 11: 3787
  • 12 Verma S, Kujur S, Sharma R, Pathak DD. ACS Omega 2022; 7: 9754
  • 13 Kralisch D, Ott D, Gericke D. Green Chem. 2015; 17: 123
  • 14 Valdemar-Aguilar CM, Manisekaran R, Acosta-Torres LS, López-Marín LM. Nanomedicine 2023; 48: 102653
  • 15 Hartman KB, Wilson LJ, Rosenblum MG. Mol. Diagn. Ther. 2008; 12: 1
  • 16 Fries CN, Curvino EJ, Chen JL, Permar SR, Fouda GG, Collier JH. Nat. Nanotechnol. 2021; 16: 1
  • 17 Lowry GV, Avellan A, Gilbertson LM. Nat. Nanotechnol. 2019; 14: 517
  • 18 Payal Payal, Pandey P. Recent Pat. Nanotechnol. 2022; 16: 45
  • 19 Mei L, Wang Q. Annu. Rev. Food Sci. Technol. 2020; 11: 339
  • 20 Kanagesan S, Aziz SB. A, Hashim M, Ismail I, Tamilselvan S, Alitheen NB. B. M, Swamy MK, Rao BP. C. Molecules 2016; 21: 312
  • 21 Bouzakher-Ghomrasni N, Taché O, Leroy J, Feltin N, Testard F, Chivas-Joly C. Talanta 2021; 234: 122619
  • 22 Muhsin TM, Hachim AK. World J. Microbiol. Biotechnol. 2014; 30: 2081
  • 23 Ebadi M, Bullo S, Buskara K, Hussein MZ, Fakurazi S, Pastorin G. Sci. Rep. 2020; 10: 21521
  • 24 Wang J, Gu H. Molecules 2015; 20: 17070
  • 25 Astruc D, Lu F, Aranzaes JR. Angew. Chem. Int. Ed. 2005; 44: 7852
  • 26 Yang H, Li G, Jiang G, Zhang Z, Hao Z. Appl. Catal., B 2023; 325: 122384
  • 27 Zhang X, Yang P. ChemNanoMat 2023; 9: e202300041
  • 28 Sunny S, Mohit M, Sheeba L, Pathan FR, Sankar GJ, Juloori H, Gadewar SG, Seth K. Synthesis 2023; in press DOI: 10.1055/a-2060-3488.
  • 29 Lawrence AS, Martin N, Sivakumar B, Cirujano FG, Dhakshinamoorthy A. ChemCatChem 2022; 14: e202200403
  • 30 Adak L, Kundu D, Roy K, Saha M, Roy A. Curr. Org. Chem. 2022; 26: 399
  • 31 Ahmed S, Ara G, Susan MA. B. H. Curr. Pharm. Biotechnol. 2023; 24: 118
  • 32 Fihri A, Bouhrara M, Nekoueishahraki B, Basset J.-M, Polshettiwar V. Chem. Soc. Rev. 2011; 40: 5181
  • 33 Bhakta S, Ghosh T. ChemCatChem 2021; 13: 828
  • 34 Polshettiwar V, Luque R, Fihri A, Zhu H, Bouhrara M, Basset J.-M. Chem. Rev. 2011; 111: 3036
  • 35 Polshettiwar V, Varma RS. Green Chem. 2010; 12: 743
  • 36 Dhiman M, Polshettiwar V. ChemCatChem 2018; 10: 881
  • 37 Kouznetsov VV, Hernández JG. RSC Adv. 2022; 12: 20807
  • 38 Schätz A, Reiser O, Stark WJ. Chem. Eur. J. 2010; 16: 8950
  • 39 Pla D, Gómez M. ACS Catal. 2016; 6: 3537
  • 40 Yasukawa T, Miyamura H, Kobayashi S. ACS Catal. 2016; 6: 7979
  • 41 Favier I, Pla D, Gómez M. Chem. Rev. 2020; 120: 1146
  • 42 Wang Q, Astruc D. Chem. Rev. 2020; 120: 1438
  • 43 Gunasekaran P, Menéndez JC, Perumal S. Green Chemistry: Synthesis of Bioactive Heterocycles . Ameta KL, Dandia A. Springer India; New Delhi: 2014: 1
  • 44 Bhakhar KA, Vaghela PV, Varakala SD, Chudasma SJ, Gajjar ND, Nagar PR, Sriram D, Dhameliya TM. ChemistrySelect 2022; 7: e202201813
  • 45 Dhameliya TM, Patel RJ, Amin RH, Sureja DK, Bodiwala KB. Mini-Rev. Org. Chem. 2022; 20: 800
  • 46 Dhameliya TM, Nagar PR, Bhakhar KA, Jivani HR, Shah BJ, Patel KM, Patel VS, Soni AH, Joshi LP, Gajjar ND. J. Mol. Liq. 2022; 348: 118329
  • 47 Bhakhar KA, Sureja DK, Dhameliya TM. J. Mol. Struct. 2022; 1248: 131522
  • 48 Dhameliya TM, Bhakhar KA, Gajjar ND, Patel KA, Devani AA, Hirani RV. J. Mol. Struct. 2022; 1248: 131473
  • 49 Dhameliya TM, Donga HA, Vaghela PV, Panchal BG, Sureja DK, Bodiwala KB, Chhabria MT. RSC Adv. 2020; 10: 32740
  • 50 Dhameliya TM, Patel RJ, Gajjar ND, Amin RH, Bodiwala KB, Sureja DK. In Advanced Nanocatalysis for Organic Synthesis and Electroanalysis . Bentham Science Publishers; Berghahn: 2022: 114
  • 51 Dhameliya TM, Raghani NR, Desai MS, Chudasma SJ, Virani KD. Synlett 2023; in press DOI: 10.1055/a-2201-7705.
  • 52 Dhameliya TM, Kathuria D, Patel TM, Dave BP, Chaudhari AZ, Vekariya DD. Curr. Top. Med. Chem. 2023; 23: 753
  • 53 Dhameliya TM, Vekariya DD, Patel HY, Patel JT. Eur. J. Med. Chem. 2023; 255: 115409
  • 54 Dhameliya TM, Devani AA, Patel KA, Shah KC. ChemistrySelect 2022; 7: e202200921
  • 55 Dhameliya TM, Chudasma SJ, Patel TM, Dave BP. Mol. Diversity 2022; 26: 2967
  • 56 Xia K, Yatabe T, Yonesato K, Yabe T, Kikkawa S, Yamazoe S, Nakata A, Yamaguchi K, Suzuki K. Angew. Chem. Int. Ed. 2022; 61: e202205873
  • 57 Wiesfeld JJ, Asakawa M, Aoshima T, Fukuoka A, Hensen EJ. M, Nakajima K. ChemCatChem 2022; 14: e202200191
  • 58 Iordanidou D, Kallitsakis MG, Tzani MA, Ioannou DI, Zarganes-Tzitzikas T, Neochoritis CG, Dömling A, Terzidis MA, Lykakis IN. Molecules 2022; 27: 4395
  • 59 Rawat M, Rawat DS. ACS Sustainable Chem. Eng. 2022; 10: 10014
  • 60 Kumar B, Babu NJ, Chowhan RL. Appl. Organomet. Chem. 2022; 36: e6742
  • 61 Kumar M, Pakshirajan K. New J. Chem. 2022; 46: 13953
  • 62 Gu AL, Zhang YX, Wu ZL, Cui HY, Hu TD, Zhao B. Angew. Chem. Int. Ed. 2022; 61: e202114817
    • 63a Hammi N, Chen S, Michon C, Royer S, El A. Mol. Catal. 2022; 519: 112104
    • 63b Dağalan Z, Can H, Daştan A, Nişancı B, Metin Ö. Tetrahedron 2022; 114: 132766
  • 64 Chen S, de Souza PM, Ciotonea C, Marinova M, Dumeignil F, Royer S, Wojcieszak R. Appl. Catal., A 2022; 633: 118527
  • 65 Wang C, Karmakar B, Awwad NS, Ibrahium HA, El-kott AF, Abdel-Daim MM, Oyouni AA. A, Al-Amer O, El-Saber Batiha G. Arabian J. Chem. 2022; 15: 103809
  • 66 Rengasamy R, Raj JP, Vijayalakshmi K, Punitha N, Kesavan M, Vajjiravel M, Elangovan J. Eur. J. Org. Chem. 2022; 16: e202101470
  • 67 Laffafchi F, Tajbakhsh M, Sarrafi Y, Maleki B, Ghani M. Polycyclic Aromat. Compd. 2022; 43: 3240
  • 68 Nasrollahzadeh M, Shafiei N, Orooji Y. Sci. Rep. 2022; 12: 6724
  • 69 Su T, Sun K, Lu G, Cai C. ACS Sustainable Chem. Eng. 2022; 10: 3872
  • 70 Sun L, Li S, Gao Z, Gao S, Gao W, Cheng X, Shang N, Gao Y, Wang C. Dalton Trans. 2022; 3096
  • 71 Han S, Chen WT, Gao ZT, Guan H, Li ZM, Tao DJ. Catal. Lett. 2022; 153: 956
  • 72 Huang L, Zhang H, Cheng Y, Sun Q, Gan T, He Q, He X, Ji H. Chin. Chem. Lett. 2022; 33: 2569
  • 73 Kharazmi A, Ghorbani-Vaghei R, Noori S, Alavinia S. Res. Chem. Intermed. 2022; 48: 1313
  • 74 Vishwakarma NK, Singh S, Vishwakarma S, Sahi AK, Patel VK, Kant S, Mahto SK. New J. Chem. 2022; 46: 2887
  • 75 Moradi P. RSC Adv. 2022; 12: 33459
  • 76 Ezabadi A, Salami M. Res. Chem. Intermed. 2022; 48: 1287
  • 77 Abubshait SA, Abubshait HA, Nabil S, Elsharif AM, Alkahtani HM, Aleanizy FS, Shaikh MN. Arabian J. Chem. 2022; 15: 103878
  • 78 Nezhad SM, Pourmousavi SA, Zare EN, Heidari G, Makvandi P. Catalysts 2022; 12: 626
  • 79 Basyach P, Saikia L. ChemistrySelect 2022; 7: e202200355
  • 80 Saeedi S, Rahmati A. RSC Adv. 2022; 12: 11740
  • 81 Khodabakhshi MR, Baghersad MH. Sci. Rep. 2022; 12: 5531
  • 82 Azarnier SG, Esmkhani M, Dolatkhah Z, Javanshir S. Sci. Rep. 2022; 12: 6104
  • 83 Mao S, Ryabchuk P, Dastgir S, Anwar M, Junge K, Beller M. ACS Appl. Nano Mater. 2022; 5: 5625
  • 84 Yamada M, Hirose Y, Lin B, Fumimoto M, Nunomura K, Natchanun S, Takahashi N, Ohki Y, Sako M, Murai K, Harada K, Arai M, Suzuki S, Nakamura T, Haruta J, Arisawa M. ACS Med. Chem. Lett. 2022; 13: 1582
  • 85 Kumar S, Kumari S, Singh S, Boruah PJ, Paul AK, Roy P, Joshi H. ACS Appl. Nano Mater. 2022; 5: 2644
  • 86 Arango-Daza JC, Lluna-Galán C, Izquierdo-Aranda L, Cabrero-Antonino JR, Adam R. ACS Catal. 2022; 12: 6906
  • 87 Poly SS, Hashiguchi Y, Nakamura I, Fujitani T, Siddiki SM. A. H. Catal. Sci. Technol. 2022; 12: 4679
  • 88 Kakavand R, Azimi SC, Jolodar OG, Shirini F, Tajik H. J. Iran. Chem. Soc. 2022; 19: 2929
  • 89 Wadhawa GC, Valvi AK, Mohite RD, Patil DD, Patil B, Gavit HJ. Mater. Today: Proc. 2022; 58: 764
  • 90 Safapoor S, Dekamin MG, Akbari A, Naimi-Jamal MR. Sci. Rep. 2022; 12: 10723
  • 92 Liu Y, Liu K, Zhang M, Zhang K, Ma J, Xiao S, Wei Z, Deng S. RSC Adv. 2021; 12: 602
  • 93 Elhaj E, Wang H, Imran M, Hegazi SE. F, Hassan M, Eldoma MA, Hakami J, Wani WA, Chaudhary AA. ACS Omega 2022; 7: 31778
  • 94 Najafi Z, Esmaili S, Khaleseh B, Babaee S, Khoshneviszadeh M, Chehardoli G, Akbarzadeh T. Sci. Rep. 2022; 12: 19917
  • 95 Agarwal S, Dutta A, Sarma D, Deori K. New J. Chem. 2022; 46: 13196
  • 96 Hasanpou Galehban M, Zeynizadeh B, Mousavi H. RSC Adv. 2022; 12: 11164
  • 97 Eivazzadeh-Keihan R, Bahrami S, Gorab MG, Sadat Z, Maleki A. Sci. Rep. 2022; 12: 10664
  • 98 Zhu P, Zhang W, Li Q, Xia H. ACS Sustainable Chem. Eng. 2022; 10: 8778
  • 99 Moeini N, Molaei S, Ghadermazi M. Res. Chem. Intermed. 2022; 48: 3109
  • 100 Pham HH, Nguyen AC. D, Nguyen CT. D, Phan NT. S, Nguyen TT. Tetrahedron Lett. 2022; 107: 154108
  • 101 Kouser M, Chowhan B, Sharma N, Gupta M. ACS Omega 2022; 7: 47619
  • 102 Mahdipour P, Moradi L, Mirzaie M. ChemistrySelect 2022; 7: e202203824
  • 103 Karimi F, Tighsazzadeh B, Asadi B, Mohammadpoor-Baltork I, Layeghi M, Mirkhani V, Tangestaninejad S, Moghadam M. RSC Adv. 2022; 12: 22180
  • 104 Fazl F, Torabi M, Yarie M, Zolfigol MA. RSC Adv. 2022; 12: 16342
  • 105 Dong LN, Zhang SZ, Zhang WL, Dong Y, Mo LP, Zhang ZH. Res. Chem. Intermed. 2022; 48: 1249
  • 106 Dong LN, Wang YM, Zhang WL, Mo LP, Zhang ZH. Appl. Organomet. Chem. 2022; 36: e6667
  • 107 Taherkhani H, Ramazani A, Sajjadifar S, Aghahossieini H, Rezaei A. ACS Omega 2022; 7: 14972
  • 108 Mohammadi M, Ghorbani-Choghamarani A. Res. Chem. Intermed. 2022; 48: 2641
  • 109 Zarei N, Torabi M, Yarie M, Zolfigol MA. Polycyclic Aromat. Compd. 2022; 43: 3072
  • 110 Chahkamali FO, Sobhani S, Sansano JM. Sci. Rep. 2022; 12: 2867
  • 111 Mashhoori MS, Sandaroos R. Sci. Rep. 2022; 12: 15364
  • 112 Sepehrmansourie H, Zarei M, Zolfigol MA, Babaee S, Azizian S, Rostamnia S. Sci. Rep. 2022; 12: 14145
  • 113 Kafi-Ahmadi L, Khademinia S, Marjani AP, Nozad E. Sci. Rep. 2022; 12: 19942
  • 114 Zare M, Moradi L. RSC Adv. 2022; 12: 34822
  • 115 Khanmohammadi-Sarabi F, Ghorbani-Choghamarani A, Aghavandi H, Zolfigol MA. Appl. Organomet. Chem. 2022; 36: 21
  • 116 Omidi M, Mobinikhaledi A. Res. Chem. Intermed. 2022; 48: 4347
  • 117 Rasooll MM, Sepehrmansourie H, Zarei M, Zolfigol MA, Rostamnia S. Sci. Rep. 2022; 12: 20812
  • 118 Zantioti-Chatzouda E.-M, Kotzabasaki V, Stratakis M. J. Org. Chem. 2022; 87: 8525
  • 119 Saadati-Moshtaghin HR, Maleki B, Tayebee R, Kahrobaei S, Abbasinohoji F. Polycyclic Aromat. Compd. 2022; 42: 885
  • 120 Anizadeh MR, Zolfigol MA, Torabi M, Yarie M, Notash B. J. Mol. Liq. 2022; 364: 120016
  • 121 Molaei S, Moeini N, Ghadermazi M. J. Organomet. Chem. 2022; 977: 122459
  • 122 Mozafari R, Gheisvandi Z, Ghadermazi M. J. Mol. Struct. 2022; 1265: 133421
  • 123 Cai Y, Yuan H, Gao Q, Wu L, Xue L, Feng N, Sun Y. Catal. Lett. 2023; 153: 460 DOI: 10.1007/s10562-022-03990-9.
  • 124 Moradi L, Mirzaei M, Sasi HR. J. Mol. Struct. 2022; 1263: 133124
  • 125 Dehkordi SS. S, Jafari AA, Albadi J, Samimi HA. Mol. Diversity 2022; 27: 177
  • 126 Ghanbarpour A, Khazaei A, Moosavi-Zare AR, Akbarpour T, Mohammadi M, Sarmasti N. Polycyclic Aromat. Compd. 2022; 43: 3192
  • 127 Xia J, Gao D, Han F, Lv R, Waterhouse GI. N, Li Y. Front. Chem. 2022; 10: 907649
  • 128 Yadav S, Dixit R, Sharma S, Dutta S, Arora B, Rana P, Kaushik B, Solanki K, Sharma RK. New J. Chem. 2022; 46: 10829
  • 129 Eisavi R, Ahmadi F. Sci. Rep. 2022; 12: 11939
  • 130 Mallik M, Monia S, Gupta M, Ghosh A, Toppo MP, Roy H. J. Alloys Compd. 2020; 829: 154623
  • 131 See ref 63b
  • 132 Ghorbani-Choghamarani A, Tahmasbi B, Moradi P. RSC Adv. 2016; 6: 43205
  • 133 Patil A, Gajare S, Rashinkar G, Salunkhe R. Catal. Lett. 2020; 150: 127
  • 134 Lakshmanan S, Ramalakshmi N. Synth. Commun. 2016; 46: 2045
  • 135 Fu Z, Qian K, Li S, Shen T, Song Q. Tetrahedron Lett. 2016; 57: 1104
  • 136 Wang S.-L, Ding J, Shi F, Liu Y.-P, Jiang B, Ma N, Tu S.-J. J. Heterocycl. Chem. 2012; 49: 521
  • 137 See ref. 91b
  • 138 Solgi S, Ghorbani-Vaghei R, Alavinia S, Izadkhah V. Polycyclic Aromat. Compd. 2022; 42: 2410
  • 139 Riadi Y, Kadhim MM, Shoja SJ, Ali MH, Mustafa YF, Sajjadi A. Synth. Commun. 2022; 52: 875