New methods of synthesis of annealed maleimides
- Authors: Panov A.A.1
- 
							Affiliations: 
							- Gause Institute of New Antibiotics
 
- Issue: Vol 60, No 4 (2024)
- Pages: 403-417
- Section: Articles
- URL: https://rjeid.com/0514-7492/article/view/672149
- DOI: https://doi.org/10.31857/S0514749224040014
- EDN: https://elibrary.ru/RZSIUO
- ID: 672149
Cite item
Abstract
This review covers the new synthetic methods for annealed maleimide derivatives, namely pyrrolo[3,4-b]-pyrrolo-4,6(1H,5H)-diones, 4H-thieno[2,3-c]-pyrrolo-4,6(5H)-diones, 4H-pyrrolo[3,4-d]thiazole-4,6(5H)-diones, 5H-pyrrolo-[3,4-b]pyridine-5,7(6H)-diones, 1H-pyrrolo-[3,4-c]pyridine-1,3(2H)-diones, and other related compounds. The publications for the last 10 years are considered, including the methods for de novo synthesis of the maleimide core and the ones which use N-substituted maleimide or halogen-substituted maleimide derivatives as the main precursor.
Keywords
Full Text
 
												
	                        About the authors
A. A. Panov
Gause Institute of New Antibiotics
							Author for correspondence.
							Email: 7745243@mail.ru
				                	ORCID iD: 0000-0002-6654-4081
				                																			                												                	Russian Federation, 							Moscow						
References
- Cappuccino C., Catalano L., Marin F., Dushaq G., Raj G., Rasras M., Rezgui R., Zambianchi M., Melucci M., Naumov P., Maini L. Cryst. Growth Des. 2020, 20, 884–891. doi: 10.1021/acs.cgd.9b01281
- Cappuccino C., Canola S., Montanari G., Lopez S. G., Toffanin S., Melucci M., Negri F., Maini L. Cryst. Growth Des. 2019, 19, 2594–2603. doi: 10.1021/acs.cgd.8b01712
- Chen K., Xie H., Jiang K., Mao J. Chem. Phys. Lett. 2016, 657, 135–141. doi: 10.1016/j.cplett.2016.05.069
- Benz S., Lopez-Andarias J., Mareda J., Sakai N., Matile S. Angew. Chem., Int. Ed. 2017, 56, 812–815. doi: 10.1002/anie.201611019
- Caruso M., Petroselli M., Cametti M. ChemistrySelect 2021, 6, 12975–12980. doi: 10.1002/slct.202103792
- Imoto H., Fujii R., Naka K. Eur. J. Org. Chem. 2018, 837–843. doi: 10.1002/ejoc.201701479
- Danilenko V.N., Simonov AY., Lakatosh S. A., Kubbutat M. H.G., Totzke F., Schachtele C., Elizarov S. M., Bekker O. B., Printsevskaya S. S., Luzikov Y. N., Reznikova M. I., Shtil A. A., Preobrazhenskaya M. N. J. Med. Chem. 2008, 51, 7731–7736. doi: 10.1021/jm800758s
- Vandyshev D.Y., Shikhaliev K. S. Molecules. 2022, 27, 5268. doi: 10.3390/molecules27165268
- Chung C.-Y., Tseng C.-C., Li S.-M., Tsai S.-E., Lin H.-Y., Wong F. F. Molecules 2021, 26, 2907. doi: 10.3390/molecules26102907
- Panov A.A., Simonov A. Y., Lavrenov S. N., Lakatosh S. A., Trenin A. S. Chem. Heterocycl. Compd. 2018, 54, 103–113. doi: 10.1007/s10593–018–2240-z
- Volvoikar P., Torney P., Tetrahedron 2021, 82, 131756. doi: 10.1016/j.tet.2020.131756
- Bansal M., Upadhyay C., Poonam; Rathi S. K.B. RSC Med. Chem. 2021, 12, 1854–1867. doi: 10.1039/D1MD00244A
- Das S. New J. Chem. 2021, 45, 20519–20536. doi: 10.1039/D1NJ03924E
- Ershov O.V., Ershova A. I. Chem. Heterocycl. Compd. 2020, 56, 518–520. doi: 10.1007/s10593–020–02693–6
- Kavitha K., Praveena K. S.S., Ramarao E. V.V.S., Murthy N. Y.S., Pal S. Curr. Org. Chem. 2016, 20, 1955–2001. doi: 10.2174/1385272820666160530145014
- Mikie T., Okamoto K., Iwasaki Y., Koganezawa T., Sumiya M., Okamoto T., Osaka I. Chem. Mater. 2022, 34, 2717–2729. doi: 10.1021/acs.chemmater.1c04196
- Kobayashi K., Kunimura R., Kogen H. Molecules 2019, 24, 4230. doi: 10.3390/molecules24234230
- Caruso M., Petroselli M., Cametti M. ChemistrySelect 2021, 6, 12975–12980. doi: 10.1002/slct.202103792
- Khitrov M.D., Platonov D. N., Belyy A. Yu., Trainov K. P., Velmiskina J. A., Medvedev M. G., Salikov R. F., Tomilov Y. V. Dyes Pigm. 2022, 203, 110344. doi: 10.1016/j.dyepig.2022.110344
- Kumar A., Banerjee S., Roy P., Sondhi S. M., Sharma A. Bioorg. Med. Chem. Lett. 2017, 27, 501–504. doi: 10.1016/j.bmcl.2016.12.031
- Yin Z., Shi W., Wu X.-F. J. Org. Chem 2023, 88, 4975–4994. doi: 10.1021/acs.joc.2c00655
- Kang C., Xu J., Li X., Wang S., Jiang G., Ji F. J. Org. Chem. 2022, 87, 10390–10397. doi: 10.1021/acs.joc.2c00673
- Ram S., Mehara P., Kumar A., Sharma A. K., Chauhan A. S., Kumar A., Das P. Mol. Catal. 2022, 530, 112606. doi: 10.1016/j.mcat.2022.112606
- Wang Y., Zhou Y., Lei M., Hou J., Jin Q., Guo D., Wu W. Tetrahedron 2019, 75, 1180–1185. doi: 10.1016/j.tet.2019.01.023
- Fu L.-Y., Ying J., Wu X.-F. J. Org. Chem. 2019, 84, 12648–12655. doi: 10.1021/acs.joc.9b01890
- Panda B., Albano G. Catalysts 2021, 11, 1531. doi: 10.3390/catal11121531
- Zeng L., Li H., Tang S., Gao X., Deng Y., Zhang G., Pao C.-W., Chen J.-L., Lee J.-F., Lei A. ACS Catal. 2018, 8, 5448–5453. doi: 10.1021/acscatal.8b00683
- Barsu N., Kalsia D., Sundararaju B. Catal. Sci. Technol. 2018, 8, 5963–5969. doi: 10.1039/C8CY02060D
- Chen L.-P., Chen J.-F., Zhang Y.-J., He X.-Y., Han Y.-F., Xiao Y.-T., Lv G.-F., Lu X., Teng F., Sun Q., Li J.-H. Org. Chem. Front. 2021, 8, 6067–6073. doi: 10.1039/D1QO01147B
- Takacs A., Varga G. M., Kardos J., Kollar L. Tetrahedron 2017, 73, 2131–2138. doi: 10.1016/j.tet.2017.02.062
- Favaretto L., Zambianchi M., Lopez S. G., Mazzanti A., Zanardi C., Seeber R., Gentili D., Valle F., Benvenuti E., Muccini M., Ruani G., Mercuri F., Milita S., Liscio F., Cavallini M., Toffanin S., Melucci M. J. Mater. Chem. C. 2017, 5, 10320–10331. doi: 10.1039/C7TC03930A
- Ikai T., Kudo T., Nagaki M., Yamamoto T., Maeda K., Kanoh S. Polymer. 2014, 55, 2139–2145. doi: 10.1016/j.polymer.2014.03.021
- Maini L., Gallino F., Zambianchi M., Durso M., Gazzano M., Rubini K., Gentili D., Manet I., Muccini M., Toffanin S., Cavallini M., Melucci M. Chem. Commun. 2015, 51, 2033–2035. doi: 10.1039/C4CC09177A
- Punzi A., Coppi D. I., Matera S., Capozzi M. A.M., Operamolla A., Ragni R., Babudri F., Farinola G. M. Org. Lett. 2017, 19, 4754–4757. https://doi.org/10.1021/acs.orglett.7b02114
- Warnan J., Labban A. E., Cabanetos C., Hoke E. T., Shukla P. K., Risko C., Bredas J.-L., McGehee M.D., Beaujuge P. M. Chem. Mater. 2014, 26, 2299–2306. doi: 10.1021/cm500172w
- Shi W., Sun S., Hu Y., Gao T., Peng Y., Wu M., Guo H., Wang J., Tetrahedron Lett. 2015, 56, 3861–3863. doi: 10.1016/j.tetlet.2015.04.097
- Dagoneau D., Kolleth A., Lumbroso A., Tanriver G., Catak S., Sulzer-Mosse S., De Mesmaeker A. Helv. Chim. Acta 2019, 102, e19000. doi: 10.1002/hlca.201900031
- Katritzky A.R., Fan W.-Q. J. Heterocycl. Chem. 1988, 25, 901–906. doi: 10.1002/jhet.5570250338
- Kharitonova O.V., Solomentseva T. A., Golubtsov I. S., Mironov A. F. Russ. J. Org. Chem. 2014, 50, 45–47. doi: 10.1134/S1070428014010084
- Huang H.-M., Li Y.-J., Ye Q., Yu W.-B., Han L., Jia J.-H., Gao J.-R. J. Org. Chem. 2014, 79, 1084–1092. doi: 10.1021/jo402540j
- Koohgard M., Hosseinpour Z., Hosseini-Sarvari M. Tetrahedron 2021, 89, 132166. doi: 10.1016/j.tet.2021.132166
- Wang L., Ma T., Qiao M., Wu Q., Shi D., Xiao W. Synthesis 2019, 51, 522–529. doi: 10.1055/s-0037–1610907
- Fujiya A., Tanaka M., Yamaguchi E., Tada N., Itoh A. J. Org. Chem. 2016, 81, 7262–7270. doi: 10.1021/acs.joc.6b00439
- Firoozi S., Hosseini-Sarvari M., Koohgard M. Green Chem. 2018, 20, 5540–5549. doi: 10.1039/C8GC03297A
- Xu Y.-W., Wang J., Wang G., Zhen L. J. Org. Chem. 2021, 86, 91–102. doi: 10.1021/acs.joc.0c01567
- Nekkanti S., Kumar N. P., Sharma P., Kamal A., Nachtigall F. M., Forero-Doria O., Santos L. S., Shankaraiah N. RSC Adv. 2016, 6, 2671–2677. doi: 10.1039/C5RA24629F
- Wang Q., Yuan T., Liu Q., Xu Y., Xie G., Lv X., Ding S., Wang X., Li C. Chem. Commun. 2019, 55, 8398–8401. doi: 10.1039/C9CC04336E
- Zhang Q., Wang B., Ma H., Ablajan K. New J. Chem. 2019, 43, 17000–17003. doi: 10.1039/C9NJ03076J
- Zhou K., Bao M., Huang J., Kang Z., Xu X., Hu W., Qian Y. Org. Biomol. Chem. 2020, 18, 409–414. doi: 10.1039/C9OB02571E
- Zhu J.-N., Wang W.-K., Jin Z.-H., Wang Q.-K., Zhao S.-Y. Org. Lett. 2019, 21, 5046–5050. doi: 10.1021/acs.orglett.9b01641
- Lv K.-H., Zhao Q.-S., Zhao K.-H., Yang J.-M., Yan S.-J. J. Org. Chem. 2022, 87, 15301–15311. doi: 10.1021/acs.joc.2c01879
- Chupakhin E., Bakulina O., Dar’in D., Krasavin M. Tetrahedron Lett. 2021, 85, 153467. doi: 10.1016/j.tetlet.2021.153467
- Zhu J.-N., Chen L.-L., Zhou R.-X., Li B., Shao Z.-Y., Zhao S.-Y. Org. Lett. 2017, 19, 6044–6047. doi: 10.1021/acs.orglett.7b02670
- Li H., Zhang S., Feng X., Yu X., Yamamoto Y., Bao M. Org. Lett. 2019, 21, 8563–8567. doi: 10.1021/acs.orglett.9b03107
- Botes D.S., Khorasani S., Duminy W., Levendis D. C., Fernandes M. A., Cryst. Growth Des. 2020, 20, 291–299. doi: 10.1021/acs.cgd.9b01167
- Yang Z.-H., Tan H.-R., An Y.-L., Zhao Y.-W., Lin H.-P., Zhao S.-Y. Adv. Synth. Catal. 2018, 360, 173–179. doi: 10.1002/adsc.201700955
- Li X., Zhang X., Zhang F., Luo X., Luo H. Adv. Synth. Catal. 2022, 364, 1683–1688. doi: 10.1002/adsc.202200251
- Zhang Y., Jiang W., Bao X., Qiu Y., Yuan Y., Yang C., Huo C. Chin. J. Chem. 2021, 39, 3238–3244. doi: 10.1002/cjoc.202100401
- Lossouarn A., Renault K., Bailly L., Frisby A., Le Nahenec-Martel P., Renard P.-Y., Sabot C., Org. Biomol. Chem. 2020, 18, 3874–3887. doi: 10.1039/D0OB00403K
- Klyuchko S.V., Chumachenko S. A., Shablykin O. V., Brovarets V. S. Russ. J. Gen. Chem. 2021, 91, 348–356. doi: 10.1134/S1070363221030026
- Zhang X., Dhawan G., Muthengi A., Liu S., Wang W., Legrisa M., Zhang W. Green Chem. 2017, 19, 3851–3855. doi: 10.1039/C7GC01380A
- Zhao H., Wang T., Qing Z., Zhai H. Chem. Commun. 2020, 56, 5524–5527. doi: 10.1039/D0CC01582B
- Pati B.V., Sagara P. S., Ghosh A., Mohanty S. R., Ravikumar P. C. J. Org. Chem. 2021, 86, 6551–6565. doi: 10.1021/acs.joc.1c00367
- Shinde V. N., Rangan K., Kumar D., Kumar A. J. Org. Chem. 2021, 86, 2328–2338. doi: 10.1021/acs.joc.0c02467
- Li B., Guo C., Shen N., Zhang X., Fan X. Org. Chem. Front. 2020, 7, 3698–3704. doi: 10.1039/D0QO01109F
- Lavrard H., Rodriguez F., Delfourne E., Bioorg. Med. Chem. 2014, 22, 4961–4967. doi: 10.1016/j.bmc.2014.06.028
- Lavrard H., Salvetti B., Mathieu V., Rodriguez F., Kiss R. Delfourne E. ChemMedChem 2015, 10, 607–609. doi: 10.1002/cmdc.201500025
- Salvetti B., Lavrard H., Delfourne E., Tetrahedron Lett. 2014, 55, 6463–6464. doi: 10.1016/j.tetlet.2014.10.002
- He J., Bai Z.-Q., Yuan P.-F., Wu L.-Z., Liu Q. ACS Catal. 2021, 11, 446–455. doi: 10.1021/acscatal.0c05005
- Aknin K., Bontemps A., Farce A., Merlet E., Belmont P., Helissey P., Chavatte P., Sari M.-A., Giorgi-Renault S., Desbene-Finck S. J. Enzyme Inhib. Med. Chem. 2022, 37, 252–268. doi: 10.1080/14756366.2021.2001806
- Jiang Y.-H., Xiao M., Yan C.-G. RSC Adv. 2016, 6, 35609–35616. doi: 10.1039/C6RA03165J
- Xiao M., Jiang Y.-H., Yan C.-G. ChemistrySelect 2017, 2, 2803–2806. doi: 10.1002/slct.201602042
- Xiao M., Sun Q., Sun J., Yan C.-G. Eur. J. Org. Chem. 2017, 46, 6861–6866. doi: 10.1002/ejoc.201701356
- Jiang Y., Yan C. Chin. J. Chem. 2016, 34, 1255–1262. doi: 10.1002/cjoc.201600504
- Du F., Li S.-J., Jiang K., Zeng R., Pan X.-C., Lan Y., Chen Y.-C., Wei Y., Angew. Chem., Int. Ed. 2020, 59, 23755–23762. doi: 10.1002/anie.202010752
- Zhao J., Chen M., Wu M., Shi L., Li H. Asian J. Org. Chem. 2022, 11, e202200042. doi: 10.1002/ajoc.202200042
- Singh B., Bhatia R., Pani B., Gupta D. J. Mol. Struct. 2020, 1200, 127084. doi: 10.1016/j.molstruc.2019.127084
- Zhang Z., Wang S., Hu C., Ma N., Zhang G., Liu Q. Tetrahedron 2018, 74, 7472–7479. doi: 10.1016/j.tet.2018.11.023
- Vepreva A., Kantin G., Krasavin M., Dar’in D. Synthesis 2022, 54, 5128–5138. doi: 10.1055/s-0037–1610790
- Inyutina A., Kantin G., Dar’in D., Krasavin M. J. Org. Chem. 2021, 86, 13673–13683. doi: 10.1021/acs.joc.1c01710
- Laha D., Meher K. B., Bankar O. S., Bhat R. G. Asian J. Org. Chem. 2022, 11, e202200062. doi: 10.1002/ajoc.202200062
- Inyutina A., Dar’in D., Kantina G., Krasavin M. Org. Biomol. Chem. 2021, 19, 5068–5071. doi: 10.1039/D1OB00773D
- Brenet S., Baptiste B., Philouze C., Berthiol F., Einhorn J. Eur. J. Org. Chem. 2013, 2013, 1041–1045. doi: 10.1002/ejoc.201201525
- Brenet S., Berthiol F., Einhorn J. Eur. J. Org. Chem. 2013, 2013, 8094–8096. doi: 10.1002/ejoc.201301329
Supplementary files
 
				
			 
					 
						 
						 
						 
						 
									

 
  
  
  Email this article
			Email this article 
 Open Access
		                                Open Access Access granted
						Access granted

































