Efficient Cesium Carbonate Promoted
N-Alkylations of Aromatic Cyclic Imides Under Microwave
Irradiation

Mercedes Isasmendi Escudero; Lautaro D. Kremenchuzky; Isabel A. Perillo; Hugo Cerecetto; María M. Blanco

doi:10.1055/s-0030-1258398

PAPER

Efficient Cesium Carbonate Promoted N-Alkylations of Aromatic Cyclic Imides Under Microwave Irradiation

Mercedes Isasmendi Escudero^a, Lautaro D. Kremenchuzky^a, Isabel A. Perillo^a, Hugo Cerecetto^b, María M. Blanco*^a
^a Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, 1113 Buenos Aires, Argentina
Fax: +54(11)49648250; e-Mail: mblanco@ffyb.uba.ar;
^b Facultad de Ciencias, Universidad de la República, Iguá 4225, 11400 Montevideo, Uruguay

Abstract

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Abstract

We present here an efficient and simple method for the N-alkylation of aromatic cyclic imides employing cesium carbonate as the base in anhydrous N,N-dimethylformamide at low temperatures (20-70 ˚C). The employment of microwave irradiation presents noteworthy advantages over conventional heating. The method is compatible with base labile functional groups.

Key words

cesium carbonate - imides - N-alkylation - microwave irradiation - nitrogen heterocycles

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References

Among others, see:

1a Chapman JM. Sowell JW. Abdalla G. Hall IH. J. Pharm. Sci. 1989, 78: 903 ; and references cited therein

1b Raasch A. Scharfernstein O. Tränkle C. Holzgrabe U. Mohr K. J. Med. Chem. 2002, 45: 3809

1c Usifoh CO. Lambert DM. Wouters J. Scriba GKE. Arch. Pharm. Pharm. Med. Chem. 2001, 334: 323

1d Collin X. Robert J.-M. Wielgosz G. Le Baut G. Bobin-Dubigeon C. Grimaud N. Petit J.-Y. Eur. J. Med. Chem. 2001, 36: 639

1e Muszalska I. Wojtyniak E. Acta Pol. Pharm. Drug Res. 2007, 64: 319 ; and references cited therein

1f Abdel-Aziz AA.-M. Eur. J. Med. Chem. 2007, 42: 614

1g Œladowska H. Filipek B. Skatula D. Sabiniarz A. Kardasz M. Potoczec J. Sieclucka-Dziuba M. Rajtar G. Kleinrok Z. Lis T. Farmaco 2002, 57: 897

Among others, see:

2a Advanced Organic Chemistry: Reactions, Mechanisms and Structures 4th ed.: Smith MB. March J. John Wiley & Sons; New York: 2001.

2b Salvi VK. Bhambi D. Jat JL. Talesara GL. ARKIVOC 2006, (xiv): 133

2c Hamprecht G, Goetz N, Wuerzer B, and Westphalen K.-O. inventors; EP 0,422,456. ; Chem. Abstr. 1991, 115, 92084z

2d Blanco MM. Shmidt MS. Perillo IA. ARKIVOC 2005, (xii): 195 ; and references cited therein

Among others, see:

3a Abdel-Monem MM. Newton NE. Weeks CE. J. Med. Chem. 1974, 17: 447

3b Gnichtel H. Chem. Ber. 1965, 98: 567

3c Furukawa Y, and Miki Y. inventors; US 7,135,576.

3d Schapira CB. Abasolo MI. Perillo IA. J. Heterocycl. Chem. 1985, 22: 577

3e Hayashi Y. Kayatani T. Sugimoto H. Suzuki M. Inomata K. Uehara A. Mizutani Y. Kitagawa T. Maeda Y. J. Am. Chem. Soc. 1995, 117: 11220

4a Œladowska H. Filipek B. Szkatula D. Sapa J. Bednarski M. Ciolkowska M. Farmaco 2005, 60: 53 ; and references cited therein

4b Hara H. inventors; JP 8285386. ; Chem. Abstr. 1982, 97, 198187

5a Perillo IA. Kremenchuzky L. Blanco MM. J. Mol. Struct. 2009, 921: 307

5b Blanco MM. Levin GJ. Schapira CB. Perillo IA. Heterocycles 2002, 57: 1881

Among others, see:

6a Blanco MM. Lorenzo MG. Perillo IA. Schapira CB. J. Heterocycl. Chem. 1996, 33: 361

6b Johnston TP. Piper JR. Stringfellow CR. Elliot RD. J. Med. Chem. 1971, 14: 345

6c Jacobs RL. inventors; US 3525747. ; Chem. Abstr. 1970, 73, 98985

6d Jaśkowska J. Kowalski P. J. Heterocycl. Chem. 2008, 45: 1371

7a Lehmann F. Synlett 2004, 2447

7b Flessner T. Doye S. J. Prakt. Chem. 1999, 341: 186

Among others, see:

8a Ostrowicki A. Koepp E. Vögtle F. Top. Curr. Chem. 1992, 161: 37

8b Dijkstra G. Kruizinga WH. Kellogg RM. J. Org. Chem. 1987, 52: 4230

8c Galli C. Org. Prep. Proced. Int. 1992, 24: 287

8d Salvatore RN. Nagle AS. Jung KW. J. Org. Chem. 2002, 67: 674

9 Blum Z. Acta Chem. Scand. 1989, 43: 248

10a Vriesema BK. Buter J. Kellog RM. J. Org. Chem. 1984, 49: 110

10b Bowman WR. Coghlan DR. Tetrahedron 1997, 53: 15787

Among others, see:

11a Link NP. Díaz JE. Orelli LR. Synlett 2009, 751 ; and references cited therein

11b Kotha S. Singh K. Tetrahedron Lett. 2004, 45: 9607

11c Maes BUW. Loones KTJ. Jonckers THM. Lemière GLF. Dommisse RA. Haemers A. Synlett 2002, 1995

12a Nivsarkar M. Kaushik MP. Catal. Commun. 2005, 6: 367

12b Yasmin N. Ray JK. Synlett 2008, 751

13a Fink DM. Synlett 2004, 2394

13b Jorapur YR. Jeong JM. Chi DY. Tetrahedron Lett. 2006, 47: 2435

14a Zacharie B. Connolly TP. Rej R. Attardo G. Penney CL. Tetrahedron 1996, 52: 2271

14b Khalafi-Nezhad A. Zare A. Parhami A. Soltani Rad MN. ARKIVOC 2006, (xii): 161

14c Torisawa Y. Nishi T. Minamikawa J.-I. Bioorg. Med. Chem. Lett. 2001, 11: 829

14d Sudini R. Wei H. Synth. Commun. 2010, 40: 81

15 Abou-Gharbia MA. inventors; US 4883875.

16 Vo-Hoang Y. Gasse C. Vidal M. Garbay C. Galons H. Tetrahedron Lett. 2004, 45: 3603

17 Wood ME. Cane-Honeysett DJ. Dowle MD. Coles SJ. Hursthouse MB. Org. Biomol. Chem. 2003, 1: 3015

18a Lidström P. Tierney J. Wathey B. Westman J. Tetrahedron 2001, 57: 9225

18b Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250

18c Bose AK. Manhas MS. Ganguly SN. Sharma AH. Banik BK. Synthesis 2002, 1578

18d Xu Y. Guo Q.-X. Heterocycles 2004, 63: 903

18e Loupy A. Microwaves in Organic Synthesis Wiley-VCH; Weinheim: 2002.

19 Bogdal D. Pielichowski J. Boron A. Synlett 1996, 873

20 Caswell LR. Campbell RD. J. Org. Chem. 1961, 26: 4175

21 Zare A. Hasaninejad A. Khalafi-Nezhad A. Moosavi Zare AR. Parhami A. Nejabat GR. ARKIVOC 2007, (i): 58

22 Gabriel S. Colman J. Ber. Dtsch. Chem. Ges. 1908, 41: 513

23 Chapman JM. Cocolas GH. Hall IH. J. Pharm. Sci. 1983, 72: 1344

24 Blanco MM. Schapira CB. Levin G. Perillo IA.
J. Heterocycl. Chem. 2005, 42: 493

25 Blanco MM. Salerno A. Perillo IA. ARKIVOC 2010, (xi): 215