Synthesis of N-Aryl and N-Heteroaryl γ-, δ-, and ε-Lactams Using Deprotometalation–Iodination and N-Arylation, and Properties Thereof

Rim Amara; Ghenia Bentabed-Ababsa; Madani Hedidi; Joseph Khoury; Haçan Awad; Ekhlass Nassar; Thierry Roisnel; Vincent Dorcet; Floris Chevallier; Ziad Fajloun; Florence Mongin

doi:10.1055/s-0036-1590798

Synthesis, Table of Contents

Synthesis 2017; 49(19): 4500-4516
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

Rim Amara

^aLaboratoire de Synthèse Organique Appliquée, Faculté des Sciences Exactes et Appliquées, Université d’Oran 1 Ahmed Ben Bella, BP 1524 El M’Naouer, 31000 Oran, Algeria

^bChimie Organique et Interfaces, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, Bâtiment 10A, Case 1003, Campus de Beaulieu, 35042 Rennes, France Email: florence.mongin@univ-rennes1.fr

,

Ghenia Bentabed-Ababsa*

^aLaboratoire de Synthèse Organique Appliquée, Faculté des Sciences Exactes et Appliquées, Université d’Oran 1 Ahmed Ben Bella, BP 1524 El M’Naouer, 31000 Oran, Algeria

,

Madani Hedidi

^aLaboratoire de Synthèse Organique Appliquée, Faculté des Sciences Exactes et Appliquées, Université d’Oran 1 Ahmed Ben Bella, BP 1524 El M’Naouer, 31000 Oran, Algeria

^bChimie Organique et Interfaces, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, Bâtiment 10A, Case 1003, Campus de Beaulieu, 35042 Rennes, France Email: florence.mongin@univ-rennes1.fr

,

Joseph Khoury

^cLaboratory of Applied Biotechnology, Azm Center for Research in Biotechnology and its Applications, EDST & Faculty of Science III, Lebanese University, Tripoli, Lebanon

,

Haçan Awad

^cLaboratory of Applied Biotechnology, Azm Center for Research in Biotechnology and its Applications, EDST & Faculty of Science III, Lebanese University, Tripoli, Lebanon

,

Ekhlass Nassar*

^dChemistry Department, Faculty of Women for Arts, Science and Education, Ain Shams University, Cairo, Egypt

,

Thierry Roisnel

^eCentre de Diffractométrie X, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, Bâtiment 10B, Campus de Beaulieu, 35042 Rennes Cedex, France

,

Vincent Dorcet

^eCentre de Diffractométrie X, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, Bâtiment 10B, Campus de Beaulieu, 35042 Rennes Cedex, France

,

Floris Chevallier

^bChimie Organique et Interfaces, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, Bâtiment 10A, Case 1003, Campus de Beaulieu, 35042 Rennes, France Email: florence.mongin@univ-rennes1.fr

,

Ziad Fajloun*

^cLaboratory of Applied Biotechnology, Azm Center for Research in Biotechnology and its Applications, EDST & Faculty of Science III, Lebanese University, Tripoli, Lebanon

,

Florence Mongin*

^bChimie Organique et Interfaces, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, Bâtiment 10A, Case 1003, Campus de Beaulieu, 35042 Rennes, France Email: florence.mongin@univ-rennes1.fr

› Author Affiliations

Abstract

All articles of this category

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 activity

Full Text

References

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

Supplementary Material