Nucleophilic Addition of Amides to 10-Alkylacridinium Cations: A Case of Double N-Nucleophilicity of Some Monoamides

Abstract

An effective synthesis of N-(10-alkyl-9,10-dihydroacridin-9-yl) derivatives of amides, ureas, and urethanes has been developed. Additionally, the spatially overloaded molecules of N,N-bis(10-alkyl-9,10-dihydroacridin-9-yl)acrylamide were obtained in the case of formamide and acrylamide.

Key words

amides - ureas - N-(10-alkyl-9,10-dihydroacridin-9-yl) derivatives - 10-alkylacridinium cations - double N-nucleophilicity

• References

• 1a Terrier F. Modern Nucleophilic Aromatic Substitution. Wiley-VCH; Weinheim: 2013
• 1b Gorelik MV. Efros LS. Osnovy Khimii i Tekhnologii Aromaticheskikh Soedinenii (Principles of the Chemistry and Technology of Aromatic Compounds). Khimia; Moscow: 1992
• 2a Wolfe JP. Tomori H. Sadighi JP. Yin J. Buchwald SL. J. Org. Chem. 2000; 65: 1158
• 2b Surry DS. Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338
• 2c Roiban G.-D. Mehler G. Reetz MT. Eur. J. Org. Chem. 2014; 2070
• 2d Henderson JL. Buchwald SL. Org Lett. 2010; 12: 4442
• 3 Anastas PT. Warner JC. Green Chemistry: Theory and Practice. Oxford University Press; New York: 1998
• 4 Constable DJ. C. Dunn PJ. Hayler JD. Humphrey GR. Leazer JL. Jr. Linderman RJ. Lorenz K. Manley J. Pearlman BA. Wells A. Zaks A. Zhang TY. Green Chem. 2007; 9: 411
• 5a Chupakhin ON. Charushin VN. van der Plas HC. Nucleophilic Aromatic Substitution of Hydrogen. Academic Press; San Diego: 1994: 367
• 5b Mąkosza M. Wojciechowski K. Chem. Rev. 2004; 104: 2631
• 6a Charushin VN. Chupakhin ON. Top. Heterocycl. Chem. 2014; 37: 1
• 6b Gulevskaya AV. Pozharskii AF. Top. Heterocycl. Chem. 2014; 37: 179
• 6c van der Plas HC. Adv. Heterocycl. Chem. 2004; 86: 1
• 6d Bunce RA. Smith CL. Knight CL. Org. Prep. Proced. Int. 2004; 36: 482
• 7a Makosza M. Wojciechowski K. Top. Heterocycl. Chem. 2014; 37: 51
• 7b Mąkosza M. Russ. Chem. Bull. 1996; 45: 491
• 8a Borovlev IV. Demidov OP. Kurnosova NA. Amangasieva GA. Avakyan EK. Chem. Heterocycl. Compd. 2015; 51: 170
• 8b Demidov OP. Borovlev IV. Amangasieva GA. Avakyan EK. Chem. Heterocycl. Compd. 2016; 52: 104
• 8c Borovlev IV. Demidov OP. Kurnosova NA. Amangasieva GA. Avakyan EK. Chem. Heterocycl. Compd. 2015; 51: 334
• 9a Borovlev IV. Demidov OP. Kurnosova NA. Amangasieva GA. Avakyan EK. Tetrahedron. Lett. 2016; 57: 3608
• 9b Borovlev IV. Demidov OP. Amangasieva GA. Avakyan EK. Kurnosova NA. ARKIVOC 2016; (iii): 58 ; http://www.arkat-usa.org/home
• 9c Amangasieva GA. Borovlev IV. Demidov OP. Kurnosova NA. Avakyan EK. Chem. Heterocycl. Compd. 2015; 51: 586
• 9d Borovlev IV. Demidov OP. Amangasieva GA. Avakyan EK. Kurnosova NA. J. Heterocycl. Chem. 2017; 54: 794
• 10 Schmidt A. Liu M. Adv. Heterocycl. Chem. 2015; 115: 287
• 11a DeJong ES. Chang C. Gilson MK. Marino JP. Biochemistry 2003; 42: 8035
• 11b Horowitz ED. Hud NV. J. Am. Chem. Soc. 2006; 128: 15380
• 11c Bellinzoni M. Buroni S. Schaeffer F. Riccardi G. Rossi ED. Alzari PM. J. Bacteriol. 2009; 191: 7531
• 11d Varvaresou A. Iakovou K. J. Mol. Model. 2011; 17: 2041
• 11e Bolla JR. Do SV. Long F. Dai L. Su C.-C. Lei H.-T. Chen X. Gerkey JE. Murphy DC. Rajashankar KR. Zhang Q. Yu EW. Nucleic Acids Res. 2012; 40: 9340
• 12a Hassan S. Laryea D. Mahteme H. Felth J. Fryknäs M. Fayad W. Linder S. Rickardson L. Gullbo J. Graf W. Påhlman L. Glimelius B. Larsson R. Nygren P. Cancer Sci. 2011; 102: 2206
• 12b Ephrussi B. Hottinguer H. Nature (London) 1950; 166: 956
• 13a Musdal Y. Hegazy UM. Aksoy Y. Mannervik B. Chem.-Biol. Interact. 2013; 205: 53
• 13b Mei Q. Li XL. Liu HJ. Zhou HB. Eur. J. Obstet. Gynecol. Reprod. Biol. 2014; 178: 12
• 14a Belmont P. Bosson J. Godet T. Tiano M. Anti-Cancer Agents Med. Chem. 2007; 7: 139
• 14b Galdino-Pitta MR. Pitta MG. R. Lima MC. A. Galdino SL. Pitta IR. Mini-Rev. Med. Chem. 2013; 13: 1256
• 14c Cain BF. Atwell GJ. Denny WA. J. Med. Chem. 1975; 18: 1110
• 15a Spicer JA. Gamage SA. Atwell GJ. Finlay GJ. Baguley BC. Denny WA. J. Med. Chem. 1997; 40: 1919
• 15b Gamage SA. Spicer JA. Rewcastle GW. Denny WA. Tetrahedron Lett. 1997; 38: 699
• 16a Dhuri SN. Lee Y.-M. Sook Seo M. Cho J. Narulkar DD. Fukuzumi S. Nam W. Dalton Trans. 2015; 44: 7634
• 16b Fukuzumi S. Koumitsu S. Hironaka K. Tanaka T. J. Am. Chem. Soc. 1987; 109: 305
• 16c Fukuzumi S. Ohkubo K. Okamoto T. J. Am. Chem. Soc. 2002; 124: 14147
• 16d Fukuzumi S. Ohkubo K. Tokuda Y. Suenobu T. J. Am. Chem. Soc. 2000; 122: 4286
• 16e Fukuzumi S. Yuasa J. Suenobu T. J. Am. Chem. Soc. 2002; 124: 12566
• 16f Fukuzumi S. Kotani H. Lee Y.-M. Nam W. J. Am. Chem. Soc. 2008; 130: 15134
• 17 Hurst TE. Taylor RJ. K. Eur. J. Org. Chem. 2017; 203
• 18a Pozharskii AF. Kuz’menko VV. Kashparov IS. Sokolov VI. Medvedeva MM. Chem. Heterocycl. Compd. 1976; 12: 304
• 18b Sheinkman AK. Potashnikova SG. Baranov SN. Russ. J. Org. Chem. 1970; 6: 614
• 18c Shchepochkin AV. Chupakhin ON. Charushin VN. Rusinov GL. Subbotina YuO. Slepukhin PA. Budnikova YuG. Russ. Chem. Bull. 2013; 62: 773
• 18d Katritzky AR. Denisenko SN. Oniciu DC. Ghiviriga I. J. Org. Chem. 1998; 63: 3450
• 19a Chupakhin ON. Charushin VN. Sidorov EO. Rusinov GL. Russ. J. Org. Chem. 1979; 15: 206
• 19b Chupakhin ON. Sidorov EO. Charushin VN. Russ. J. Org. Chem. 1979; 15: 117
• 20 CCDC 1480861 (5a; crystallized from CHCl₃) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
• 21 CCDC 1480843 (6a; crystallized from CHCl₃) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
• 22 Gottlieb HE. Kotlyar V. Nudelman A. J. Org. Chem. 1997; 62: 7512