Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2017; 49(19): 4500-4516
DOI: 10.1055/s-0036-1590798
DOI: 10.1055/s-0036-1590798
paper
Synthesis of N-Aryl and N-Heteroaryl γ-, δ-, and ε-Lactams Using Deprotometalation–Iodination and N-Arylation, and Properties Thereof
We thank the Ministère de l’Enseignement supérieur et de la Recherche scientifique Algérien (M.H.), the Centre National de la Recherche Scientifique, the Institut Universitaire de France and Rennes Métropole (F.M.). We acknowledge FEDER founds (D8 VENTURE Bruker AXS diffractometer) and Thermofisher (generous gift of 2,2,6,6-tetramethylpiperidine). This research has been partly performed as part of the CNRS PICS project ‘Bimetallic synergy for the functionalization of heteroaromatics’Further Information
Publication History
Received: 18 May 2017
Accepted: 22 May 2017
Publication Date:
19 July 2017 (online)
Abstract
Xanthone, thioxanthone, fluorenone, benzophenone, 2-benzoylpyridine, dibenzofuran, and dibenzothiophene were deprotonated using a base prepared in situ from MCl2·TMEDA (M = Zn or Cd; TMEDA = N,N,N′,N′-tetramethylethylenediamine) and lithium 2,2,6,6-tetramethylpiperidide in a 1:3 ratio, as demonstrated by subsequent iodolysis. The different aryl halides were involved as partners in the N-arylation of pyrrolidin-2-one. In the presence of copper(I) iodide and tripotassium phosphate, and using dimethyl sulfoxide as solvent, the reactions could be performed in yields ranging from 40 to 70%. Most of the products were tested for their antimicrobial, antifungal, antioxidant, and cytotoxic (MCF-7) activity.
Key words
C–N bond formation - deprotonative metalation - lactam - aromatic compound - antimicrobial activity - antifungal activitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590798.
- Supporting Information
- CIF File
-
References
- 1 Present address: Département de Chimie, Faculté des Sciences Exactes et Informatique, Université Hassiba Benbouali de Chlef, Hay Es-Salem, RN 19, 02000 Chlef, Algeria.
- 2a Gschwend HW. Rodriguez HR. Org. React. 1979; 26: 1
- 2b Beak P. Snieckus V. Acc. Chem. Res. 1982; 15: 306
- 2c Snieckus V. Chem. Rev. 1990; 90: 879
- 2d Gant TG. Meyers AI. Tetrahedron 1994; 50: 2297
- 2e Schlosser M. Organoalkali Chemistry . In Organometallics in Synthesis: A Manual . 2nd ed.; Schlosser M. John Wiley & Sons; Hoboken: 2002: Chap. 1, 1
- 2f Chinchilla R. Najera C. Yus M. ARKIVOC 2007; 152 ; http://www.arkat-usa.org/home
- 3a Mulvey RE. Mongin F. Uchiyama M. Kondo Y. Angew. Chem. Int. Ed. 2007; 46: 3802
- 3b Mulvey RE. Acc. Chem. Res. 2009; 42: 743
- 3c Haag B. Mosrin M. Ila H. Malakhov V. Knochel P. Angew. Chem. Int. Ed. 2011; 50: 9794
- 3d Mongin F. Uchiyama M. Curr. Org. Chem. 2011; 15: 2340
- 3e Mongin F. Harrison-Marchand A. Chem. Rev. 2013; 113: 7563
- 3f Harford PJ. Peel AJ. Chevallier F. Takita R. Mongin F. Uchiyama M. Wheatley AE. H. Dalton Trans. 2014; 43: 14181
- 4a L’Helgoual’ch JM. Seggio A. Chevallier F. Yonehara M. Jeanneau E. Uchiyama M. Mongin F. J. Org. Chem. 2008; 73: 177
- 4b García-Álvarez P. Mulvey RE. Parkinson JA. Angew. Chem. Int. Ed. 2011; 50: 9668
- 5 Fuentes MA. Kennedy AR. Mulvey RE. Parkinson JA. Rantanen T. Robertson SD. Snieckus V. Chem. Eur. J. 2015; 21: 14812
- 6a Seggio A. Lannou MI. Chevallier F. Nobuto D. Uchiyama M. Golhen S. Roisnel T. Mongin F. Chem. Eur. J. 2007; 13: 9982
- 6b Seggio A. Chevallier F. Vaultier M. Mongin F. J. Org. Chem. 2007; 72: 6602
- 6c Snégaroff K. Komagawa S. Chevallier F. Gros PC. Golhen S. Roisnel T. Uchiyama M. Mongin F. Chem. Eur. J. 2010; 16: 8191
- 6d Kadiyala RR. Tilly D. Nagaradja E. Roisnel T. Matulis VE. Ivashkevich OA. Halauko YS. Chevallier F. Gros PC. Mongin F. Chem. Eur. J. 2013; 19: 7944
- 6e Hedidi M. Bentabed-Ababsa G. Derdour A. Halauko YS. Ivashkevich OA. Matulis VE. Chevallier F. Roisnel T. Dorcet V. Mongin F. Tetrahedron 2016; 72: 2196
- 7 Klapars A. Antilla JC. Huang X. Buchwald SL. J. Am. Chem. Soc. 2001; 123: 7727
- 8a Monnier F. Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
- 8b Beletskaya IP. Cheprakov AV. Organometallics 2012; 31: 7753
- 9a Klapars A. Huang X. Buchwald SL. J. Am. Chem. Soc. 2002; 124: 7421
- 9b Kang S.-K. Kim D.-H. Park J.-N. Synlett 2002; 427
- 9c Crawford KR. Padwa A. Tetrahedron Lett. 2002; 43: 7365
- 9d Padwa A. Crawford KR. Rashatasakhon P. Rose M. J. Org. Chem. 2003; 68: 2609
- 9e Soares Do Rêgo Barros O. Nogueira CW. Stangherlin EC. Menezes PH. Zeni G. J. Org. Chem. 2006; 71: 1552
- 9f Heinrich DM. Flanagan JU. Jamieson SM. F. Silva S. Rigoreau LJ. M. Trivier E. Raynham T. Turnbull AP. Denny WA. Eur. J. Med. Chem. 2013; 62: 738
- 9g Wang M. Zhang Z. Xie F. Zhang W. Chem. Commun. 2014; 50: 3163
- 10 Güell I. Ribas X. Eur. J. Org. Chem. 2014; 3188
- 11 Haas D. Sustac-Roman D. Schwarz S. Knochel P. Org. Lett. 2016; 18: 6380
- 12a Lin W. Baron O. Knochel P. Org. Lett. 2006; 8: 5673
- 12b Wunderlich SH. Knochel P. Angew. Chem. Int. Ed. 2007; 46: 7685
- 12c Mosrin M. Knochel P. Org. Lett. 2009; 11: 1837
- 12d Bresser T. Mosrin M. Monzon G. Knochel P. J. Org. Chem. 2010; 75: 4686
- 13 Snégaroff K. L’Helgoual’ch J.-M. Bentabed-Ababsa G. Nguyen TT. Chevallier F. Yonehara M. Uchiyama M. Derdour A. Mongin F. Chem. Eur. J. 2009; 15: 10280
- 14 Hedidi M. Erb W. Lassagne F. Halauko YS. Ivashkevich OA. Matulis VE. Roisnel T. Bentabed-Ababsa G. Mongin F. RSC Adv. 2016; 6: 63185
- 15 Snégaroff K. Komagawa S. Yonehara M. Chevallier F. Gros PC. Uchiyama M. Mongin F. J. Org. Chem. 2010; 75: 3117
- 16 Armstrong DR. Kennedy AR. Mulvey RE. Parkinson JA. Robertson SD. Chem. Sci. 2012; 3: 2700
- 17a Eaton PE. Higuchi H. Millikan R. Tetrahedron Lett. 1987; 28: 1055
- 17b Kruger C. Thiele KH. Dargatz M. Bartik T. J. Organomet. Chem. 1989; 362: 147
- 18a Chevallier F. Halauko YS. Pecceu C. Nassar IF. Dam TU. Roisnel T. Matulis VE. Ivashkevich OA. Mongin F. Org. Biomol. Chem. 2011; 9: 4671
- 18b Chevallier F. Blin T. Nagaradja E. Lassagne F. Roisnel T. Halauko YS. Matulis VE. Ivashkevich OA. Mongin F. Org. Biomol. Chem. 2012; 10: 4878
- 18c Nagaradja E. Chevallier F. Roisnel T. Dorcet V. Halauko YS. Ivashkevich OA. Matulis VE. Mongin F. Org. Biomol. Chem. 2014; 12: 1475
- 18d Marquise N. Bretel G. Lassagne F. Chevallier F. Roisnel T. Dorcet V. Halauko YS. Ivashkevich OA. Matulis VE. Gros PC. Mongin F. RSC Adv. 2014; 4: 19602
- 18e Nagaradja E. Bentabed-Ababsa G. Scalabrini M. Chevallier F. Philippot S. Fontanay S. Duval RE. Halauko YS. Ivashkevich OA. Matulis VE. Roisnel T. Mongin F. Bioorg. Med. Chem. 2015; 23: 6355
- 19a Fotouhi N. Galakatos NG. Kemp DS. J. Org. Chem. 1989; 54: 2803
- 19b Kitamura T. Kobayashi S. Taniguchi H. Hori K. J. Am. Chem. Soc. 1991; 113: 6240
- 19c Bekele H. Nesloney CL. McWilliams KW. Zacharias NM. Chitnumsub P. Kelly JW. J. Org. Chem. 1997; 62: 2259
- 19d Tye H. Eldred C. Wills M. J. Chem. Soc., Perkin Trans. 1 1998; 457
- 19e Oliveira AM. A. G. Raposo MM. M. Oliveira-Campos AM. F. Griffiths J. Machado AE. H. Helv. Chim. Acta 2003; 86: 2900
- 19f Werle S. Robert F. Bouas-Laurent H. Landais Y. Tetrahedron Lett. 2007; 48: 8909
- 19g Unger Y. Meyer D. Molt O. Schildknecht C. Muenster I. Wagenblast G. Strassner T. Angew. Chem. Int. Ed. 2010; 49: 10214
- 19h Lakshminarayana N. Prasad YR. Gharat L. Thomas A. Narayanan S. Raghuram A. Srinivasan CV. Gopalan B. Eur. J. Med. Chem. 2010; 45: 3709
- 19i Han C. Xie G. Xu H. Zhang Z. Yu D. Zhao Y. Yan P. Deng Z. Li Q. Liu S. Chem. Eur. J. 2011; 17: 445
- 20a Haenel MW. Jakubik D. Rothenberger E. Schroth G. Chem. Ber. 1991; 124: 1705
- 20b Diaz H. Kelly JW. Tetrahedron Lett. 1991; 32: 5725
- 20c Baret P. Beguin C. Gaude D. Gellon G. Mourral C. Pierre JL. Serratrice G. Favier A. Tetrahedron 1994; 50: 2077
- 20d Kranenburg M. van der Burgt YE. M. Kamer PC. J. van Leeuwen PW. N. M. Goubitz K. Fraanje J. Organometallics 1995; 14: 3081
- 20e Iserloh U. Curran DP. Kanemasa S. Tetrahedron: Asymmetry 1999; 10: 2417
- 20f Deng Y. Chang CJ. Nocera DG. J. Am. Chem. Soc. 2000; 122: 410
- 20g Ooi T. Saito A. Maruoka K. Chem. Lett. 2001; 1108
- 20h Zhang W. Su L. Sun W.-H. Jin X. J. Chem. Res., Synop. 2003; 734
- 20i Iserloh U. Oderaotoshi Y. Kanemasa S. Curran DP. Org. Synth. 2003; 80: 46
- 20j Clare B. Sarker N. Shoemaker R. Hagadorn JR. Inorg. Chem. 2004; 43: 1159
- 20k Skene WG. Berl V. Risler H. Khoury R. Lehn J.-M. Org. Biomol. Chem. 2006; 4: 3652
- 20l Sato Y. Yamasaki R. Saito S. Angew. Chem. Int. Ed. 2009; 48: 504
- 20m Ireland BJ. Wheaton CA. Hayes PG. Organometallics 2010; 29: 1079
- 20n Asensio G. Cuenca AB. Esteruelas MA. Medio-Simon M. Olivan M. Valencia M. Inorg. Chem. 2010; 49: 8665
- 20o Han C.-M. Xie G.-H. Li J. Zhang Z.-S. Xu H. Deng Z.-P. Zhao Y. Yan P.-F. Liu S.-Y. Chem. Eur. J. 2011; 17: 8947
- 20p Wheaton CA. Hayes PG. J. Organomet. Chem. 2012; 704: 65
- 20q Rosario-Amorin D. Duesler EN. Paine RT. Hay BP. Delmau LH. Reilly SD. Gaunt AJ. Scott BL. Inorg. Chem. 2012; 51: 6667
- 20r Graham DJ. Zheng S.-L. Nocera DG. ChemSusChem 2014; 7: 2449
- 21a Dunkerton LV. Barot BC. Nigam A. J. Heterocycl. Chem. 1987; 24: 749
- 21b Katritzky AR. Perumal S. J. Heterocycl. Chem. 1990; 27: 1737
- 21c Kuehm-Caubère C. Adach-Becker S. Fort Y. Caubère P. Tetrahedron 1996; 52: 9087
- 21d Rossi R. Bellina F. Ciucci D. Carpita A. Fanelli C. Tetrahedron 1998; 54: 7595
- 21e Reich HJ. Gudmundsson BO. Green DP. Bevan MJ. Reich IL. Helv. Chim. Acta 2002; 85: 3748
- 21f Tronnier A. Risler A. Langer N. Wagenblast G. Muenster I. Strassner T. Organometallics 2012; 31: 7447
- 21g Pittalis M. Azzena U. Pisano L. Tetrahedron 2013; 69: 207
- 22a Kadish KM. Ou Z. Shao J. Gros CP. Barbe J.-M. Jerome F. Bolze F. Burdet F. Guilard R. Inorg. Chem. 2002; 41: 3990
- 22b Voituriez A. Fiaud J.-C. Schulz E. Tetrahedron Lett. 2002; 43: 4907
- 22c Faure S. Stern C. Guilard R. Harvey PD. Inorg. Chem. 2005; 44: 9232
- 22d Korang J. Grither WR. McCulla RD. J. Am. Chem. Soc. 2010; 132: 4466
- 23 Hedidi M. Bentabed-Ababsa G. Derdour A. Roisnel T. Dorcet V. Chevallier F. Picot L. Thiéry V. Mongin F. Bioorg. Med. Chem. 2014; 22: 3498
- 24 Hedidi M. Erb W. Bentabed-Ababsa G. Chevallier F. Picot L. Thiery V. Bach S. Ruchaud S. Roisnel T. Dorcet V. Mongin F. Tetrahedron 2016; 72: 6467
- 25 Triggle DJ. Dictionary of Pharmacological Agents . Chapman & Hall/CRC; Boca Raton: 1996
- 26 Singh P. Dimitriou V. Mahajan RP. Crossley AW. Br. J. Anaesth. 1993; 71: 685
- 27 Nootropil, NetDoctor.co.uk, 8th July 2004, Retrieved 21 September 2009.
- 28 Gottlieb HE. Kotlyar V. Nudelman A. J. Org. Chem. 1997; 62: 7512
- 29 Altomare A. Burla MC. Camalli M. Cascarano GL. Giacovazzo C. Guagliardi A. Moliterni AG. G. Polidori G. Spagna R. J. Appl. Crystallogr. 1999; 32: 115
- 30 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112
- 31 Farrugia LJ. J. Appl. Crystallogr. 2012; 45: 849
- 32 Sheldrick GM. Acta Crystallogr., Sect. A 2015; 71: 3
- 33 Sheldrick GM. Acta Crystallogr., Sect. C 2015; 71: 3
- 34 Farrugia LJ. J. Appl. Crystallogr. 1997; 30: 565
- 35 Kjonaas RA. Hoffer RK. J. Org. Chem. 1988; 53: 4133
- 36 Odrowaz-Sypniewski MR. Tsoungas PG. Varvounis G. Cordopatis P. Tetrahedron Lett. 2009; 50: 5981
- 37 Hollins RA. Salim VM. Tetrahedron Lett. 1979; 20: 591
- 38 Koelsch CF. J. Am. Chem. Soc. 1932; 54: 4744
- 39 Huntress EH. Pfister KIII. Pfister KH. T. J. Am. Chem. Soc. 1942; 64: 2845
- 40 Gilman H. Young RV. J. Am. Chem. Soc. 1934; 56: 1415
- 41 Yang H. Li Y. Jiang M. Wang J. Fu H. Chem. Eur. J. 2011; 17: 5652
- 42 Gilman H. Avakian S. J. Am. Chem. Soc. 1945; 67: 349
- 43 Tsang KY. Diaz H. Graciani N. Kelly JW. J. Am. Chem. Soc. 1994; 116: 3988
- 44a Nag M. Jenks WS. J. Org. Chem. 2004; 69: 8177
- 44b Katritzky AR. Perumal S. Magn. Reson. Chem. 1990; 28: 914
- 45 Meyer WL. Vaughan WR. J. Org. Chem. 1957; 22: 1554
- 46 Desai LV. Malik HA. Sanford MS. Org. Lett. 2006; 8: 1141
- 47 Braunholtz JT. Mann FG. J. Chem. Soc. 1957; 4174
- 48 Lawson CP. A. T. Slawin AM. Z. Westwood NJ. Chem. Commun. 2011; 47: 1057
- 49 Guazzelli G. Duffy LA. Procter DJ. Org. Lett. 2008; 10: 4291
- 50 Deng W. Zhang C. Liu M. Zou Y. Liu L. Guo Q.-X. Chin. J. Chem. 2005; 23: 1241
- 51 Bassoli A. Borgonovo G. Busnelli G. Morini G. Eur. J. Org. Chem. 2006; 1656
- 52 Phillips DP. Zhu X.-F. Lau TL. He X. Yang K. Liu H. Tetrahedron Lett. 2009; 50: 7293
- 53 Huang X. Anderson KW. Zim D. Jiang L. Klapars A. Buchwald SL. J. Am. Chem. Soc. 2003; 125: 6653
- 54 Reppe W. Justus Liebigs Ann. Chem. 1955; 596: 158
- 55 Mitsuda S. Fujiwara T. Kimigafukuro K. Monguchi D. Mori A. Tetrahedron 2012; 68: 3585
- 56 Wang Q. Schreiber SL. Org. Lett. 2009; 11: 5178
- 57 Fang P. Li M. Ge H. J. Am. Chem. Soc. 2010; 132: 11898
- 58 Kornet MJ. J. Pharm. Sci. 1979; 68: 350
- 59 Kalyani D. Dick AR. Anani WQ. Sanford MS. Tetrahedron 2006; 62: 11483