RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
Synthesis 2020; 52(21): 3263-3271
DOI: 10.1055/s-0040-1707864
DOI: 10.1055/s-0040-1707864
special topic
Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones
Authors
The synthetic part of this work was made with financial support from the government assignment for the Federal Research Center, Kazan Scientific Center of the Russian Academy of Sciences. The X-ray studies were supported by Russian Science Foundation (Grant No. 19-13-00238). The X-ray measurements were performed using shared experimental facilities supported by an Institute of General and Inorganic Chemistry, Russian Academy of Sciences state assignment.
Weitere Informationen
Publikationsverlauf
Received: 26. März 2020
Accepted after revision: 15. Mai 2020
Publikationsdatum:
10. Juni 2020 (online)
Published as part of the Special Topic Recent Advances in Amide Bond Formation
Abstract
Imidazolidin-2-one and 1,3-benzodiazepin-2-one scaffolds are structural motifs of many biologically active compounds. Herein, we report a highly regioselective acid-catalyzed intramolecular nucleophilic cyclization/intermolecular electrophilic substitution reaction sequence of (2,2-dialkoxyethyl)ureas. The reaction benefits from readily available starting materials, a simple workup procedure, moderate to high yields of target compounds, and provides a convenient entry to previously unknown 4-(het)arylimidazolidinones and 5-(het)arylbenzodiazepinones. The proposed mechanism of the reaction is also discussed.
Key words
(2,2-dialkoxyethyl)ureas - imidazolidin-2-ones - 1,3-benzodiazepin-2-ones - cyclization - cyclic ureasSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707864.
- Supporting Information (PDF)
-
References
- 1 De Clercq PJ. Chem. Rev. 1997; 97: 1755
- 2 Zempleni J, Wijeratne SS. K, Hassan YI. BioFactors 2009; 35: 36
- 3 Abberley L, Bebius A, Beswick PJ, Billinton A, Collis KL, Dean DK, Fonfria E, Gleave RJ, Medhurst SJ, Michel AD, Moses AP, Patel S, Roman SA, Scoccitti T, Smith B, Steadman JG. A, Walter DS. Bioorg. Med. Chem. Lett. 2010; 20: 6370
- 4 Shue H.-J, Chen X, Shih N.-Y, Blythin DJ, Paliwal S, Lin L, Gu D, Schwerdt JH, Shah S, Reichard GA, Piwinski JJ, Duffy RA, Lachowicz JE, Coffin VL, Liu F, Nomeir AA, Morgan CA, Varty GB. Bioorg. Med. Chem. Lett. 2005; 15: 3896
- 5 Peretto I, Fossati C, Giardina GA. M, Giardini A, Guala M, La Porta E, Petrillo P, Radaelli S, Radice L, Raveglia LF, Santoro E, Scudellaro R, Scarpitta F, Cerri A, Menegon S, Dondio GM, Rizzi A, Armani E, Amari G, Civelli M, Villetti G, Patacchini R, Bergamaschi M, Bassani F, Delcanale M, Imbimbo BP. J. Med. Chem. 2007; 50: 1693
- 6 Yoon S, Kim JH, Yoon I, Kim C, Kim S.-E, Koh Y, Jeong SJ, Lee J, Kim S, Lee J. Bioorg. Med. Chem. Lett. 2016; 26: 3038
- 7 Park H, Min K, Kwak H.-S, Koo KD, Lim D, Seo S.-W, Choi J.-U, Platt B, Choi D.-Y. Bioorg. Med. Chem. Lett. 2008; 18: 2900
- 8 De Lucca GV. Bioorg. Med. Chem. Lett. 1997; 7: 495
- 9 Kazmierski WM, Furfine E, Gray-Nunez Y, Spaltenstein A, Wright L. Bioorg. Med. Chem. Lett. 2004; 14: 5685
- 10 Nudelman AA, Marcovici-Mizrahi D, Nudelman AA, Flint D, Wittenbach V. Tetrahedron 2004; 60: 1731
- 11 Francavilla C, Turtle ED, Kim B, O’Mahony DJ. R, Shiau TP, Low E, Alvarez NJ, Celeri CE, D’Lima L, Friedman LC, Ruado FS, Xu P, Zuck ME, Anderson MB, Najafi R, Jain RK. Bioorg. Med. Chem. Lett. 2011; 21: 3029
- 12 Shuter J. Ther. Clin. Risk Manage. 2008; 4: 1023
- 13 Ottenheijm HC. J, Van Den Broek LA. G. M, Ballesta JP. G, Zylicz Z. Prog. Med. Chem. 1986; 23: 219
- 14 Vose JM, Panwalkar A, Belanger R, Coiffier B, Baccarani M, Gregory SA, Facon T, Fanin R, Caballero D, Ben-Yehuda D, Giles F. Leuk. Lymphoma 2007; 48: 39
- 15 De Lucca GV, Kim UT, Liang J, Cordova B, Klabe RM, Garber S, Bacheler LT, Lam GN, Wright MR, Logue KA, Erickson-Viitanen S, Ko SS, Trainor GL. J. Med. Chem. 1998; 41: 2411
- 16 De Lucca GV. J. Org. Chem. 1998; 63: 4755
- 17 De Lucca GV, Liang J, De Lucca I. J. Med. Chem. 1999; 42: 135
- 18 Kaltenbach RF, Patel M, Waltermire RE, Harris GD, Stone BR, Klabe RM, Garber S, Bacheler LT, Cordova BC, Logue K, Wright MR, Erickson-Viitanen S, Trainor GL. Bioorg. Med. Chem. Lett. 2003; 13: 605
- 19 Lam PY. S, Ru Y, Jadhav PK, Aldrich PE, De Lucca GV, Eyermann CJ, Chang C.-H, Emmett G, Holler ER, Daneker WF, Li L, Confalone PN, McHugh RJ, Han Q, Li R, Markwalder JA, Seitz SP, Sharpe TR, Bacheler LT, Rayner MM, Klabe RM, Shum L, Winslow DL, Kornhauser DM, Jackson DA, Erickson-Viitanen S, Hodge CN. J. Med. Chem. 1996; 39: 3514
- 20 Patel M, Rodgers JD, McHugh RJ, Johnson BL, Cordova BC, Klabe RM, Bacheler LT, Erickson-Viitanen S, Ko SS. Bioorg. Med. Chem. Lett. 1999; 9: 3217
- 21 Del Vecchio E, Boga C, Forlani L, Tozzi S, Micheletti G, Cino S. J. Org. Chem. 2015; 80: 2216
- 22 Boga C, Cino S, Micheletti G, Padovan D, Prati L, Mazzanti A, Zanna N. Org. Biomol. Chem. 2016; 14: 7061
- 23 Li C.-D, Mella SL, Sartorelli AC. J. Med. Chem. 1981; 24: 1089
- 24 Markosyan AI, Dilanyan SV, Gabrielyan SA, Arsenyan FG, Sukasyan RS, Garibdzhanyan BT. Pharm. Chem. J. 2010; 44: 352
- 25 Abdel Gawad NM, Georgey HH, Youssef RM, El-Sayed NA. Eur. J. Med. Chem. 2010; 45: 6058
- 26 Liao W, Hu G, Guo Z, Sun D, Zhang L, Bu Y, Li Y, Liu Y, Gong P. Bioorg. Med. Chem. 2015; 23: 4410
- 27 Mayer P, Brunel P, Chaplain C, Piedecoq C, Calmel F, Schambel P, Chopin P, Wurch T, Pauwels PJ, Marien M, Vidaluc J.-L, Imbert T. J. Med. Chem. 2000; 43: 3653
- 28 Schneider W, Diller W. In Ullmann’s Encyclopedia of Industrial Chemistry . Wiley-VCH; Weinheim: 2000: 624
- 29 Senet J.-P. C. R. Acad. Sci., Ser. IIC: Chim. 2000; 3: 505
- 30 Tamboli AH, Bandal HA, Kim H. Chem. Eng. J. 2016; 306: 826
- 31 Badru R, Singh B. RSC Adv. 2014; 4: 38978
- 32 Chouhan M, Sharma R, Nair VA. Org. Lett. 2012; 14: 5672
- 33 Ambroise L, Dumez E, Szeki A, Jackson RF. W. Synthesis 2002; 2296
- 34 Kale A, Puranik V, Deshmukh A. Synthesis 2007; 1159
- 35 Humphries PS, Bersot R, Kincaid J, Mabery E, McCluskie K, Park T, Renner T, Riegler E, Steinfeld T, Turtle ED, Wei Z.-L, Willis E. Bioorg. Med. Chem. Lett. 2018; 28: 293
- 36 Taniguchi T, Suzuki T, Satoh H, Shichibu Y, Konishi K, Monde K. J. Am. Chem. Soc. 2018; 140: 15577
- 37 Micheletti G, Delpivo C, Baccolini G. Green Chem. Lett. Rev. 2013; 6: 135
- 38 Del Vecchio A, Caillé F, Chevalier A, Loreau O, Horkka K, Halldin C, Schou M, Camus N, Kessler P, Kuhnast B, Taran F, Audisio D. Angew. Chem. Int. Ed. 2018; 57: 9744
- 39 Xu M, Jupp AR, Ong MS. E, Burton KI, Chitnis SS, Stephan DW. Angew. Chem. Int. Ed. 2019; 58: 5707
- 40 Martínez-Pardo P, Blay G, Escrivá-Palomo A, Sanz-Marco A, Vila C, Pedro JR. Org. Lett. 2019; 21: 4063
- 41 Melyashova AS, Smolobochkin AV, Gazizov AS, Voronina JK, Burilov AR, Pudovik MA. Tetrahedron 2019; 75: 130681
- 42 Smolobochkin AV, Rizbayeva TS, Melyashova AS, Burilov AR, Pudovik MA, Sinyashin OG, Gazizov AS. ChemistrySelect 2019; 4: 9322
- 43 Smolobochkin AV, Rizbayeva TS, Gazizov AS, Voronina JK, Dobrynin AB, Gildebrant AV, Strelnik AG, Sazykin IS, Burilov AR, Pudovik MA, Sazykina MA. Eur. J. Org. Chem. 2019; 5709
- 44 Louwrier S, Ostendorf M, Boom A, Hiemstra H, Speckamp WN. Tetrahedron 1996; 52: 2603
- 45 Koot W.-J, Hiemstra H, Speckamp WN. Tetrahedron Lett. 1992; 33: 7969
- 46 Rutjes FP. J. T, Udding JH, Hiemstra H, Speckamp WN. Recl. Trav. Chim. Pays-Bas 1994; 113: 145
- 47 Luker T, Koot W.-J, Hiemstra H, Speckamp WN. J. Org. Chem. 1998; 63: 220
- 48 Khakimov MS, Gazizov AS, Burilov AR, Pudovik MA, Konovalov AI. Russ. J. Gen. Chem. 2009; 79: 1163
- 49 Gazizov AS, Khakimov MS, Burilov AR, Pudovik MA, Krivolapov DB, Litvinov IA, Konovalov AI. Russ. Chem. Bull. 2009; 58: 238
- 50 Burilov AR, Gazizov AS, Khakimov MS, Kharitonova NI, Pudovik MA, Konovalov AI. Russ. J. Gen. Chem. 2008; 78: 2411
- 51 Burilov AR, Khakimov MS, Gazizov AS, Pudovik MA, Syakaev VV, Krivolapov DB, Konovalov AI. Mendeleev Commun. 2008; 18: 54
- 52 Forrest TP, Dauphinee GA, Chen FM. F. Can. J. Chem. 1974; 52: 2725
- 53 Smolobochkin AV, Gazizov AS, Burilov AR, Pudovik MA. Russ. J. Org. Chem. 2019; 55: 373
- 54 Cambridge Structural Database System, Version 5.39. Cambridge Crystallographic Data Centre; Cambridge: 2017
- 55 Eliel EL, Allinger NL, Angyal SJ, Morrison GA. Conformational Analysis . John Wiley & Sons; New York: 1965: 524
- 56 Hamor TA, Martin IL. X-ray Crystallography and Drug Action . Horn AS, De Ranter CJ. OUP; Oxford: 1984. 275
- 57 Butcher HJ, Hamor TA. Acta Crystallogr., Sect. C 1985; 41: 1081