How to cite this paper
Chaturvedi, D., Chaturvedi, A., Dash, P & Mishra, N. (2015). An efficient method for the synthesis of substituted N-aryl lactams.Current Chemistry Letters, 4(3), 119-126.
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1. (a) Muktar T.A., Wright G. D. (2005) Streptogramins, oxazolidinones, and other inhibitors of bacterial protein synthesis. Chem. Rev.105, 529-542; (b) Horton D. A., Bourne G. T., Smythe M. L. (2003) The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem. Rev. 103, 893–930; (c) Fischer C., Koening B. (2011) Palladium and copper mediated N-aryl bond formation reactions for the synthesis of biologically active compounds. Beilstein J. Org. Chem. 7, 59-74; (d) Bari S. S., Bhalla A. (2010) Spirocyclic B-lactams: Synthesis and biological evaluation of novel heterocycles. Top. Heterocycl. Chem. 22, 49-99.
2. (a) Dimmock J. R., Jha A., Zello G. A., Quail J. W., Oloo E. O., Nienaber K. H., Kowalczyk E. S., Allen T. M., Santos C. L., De Clercq E., Balzarini J., Manavathu E. K., Stables J. P. (2012) Cytotoxic N-[4-(3-aryl-3-oxo-1-propenyl)phenylcarbonyl]-3,5-bis(phenylmethylene)-4-piperidones and related compounds. Eur. J. Med. Chem. 37, 961-972; (b) Jha A., Mukherjee C., Prasad A. K., Parmar V. S., De Clercq E., Balzarini J., Stables J. P., Manavathu E. K., Srivastava A., Sharma R. K., Nienaber K. H., Zello G. A., Dimmock J. R. (2007) E,E,E-1-(4-Arylamino-4-oxo-2-butenoyl)-3,5-bis(arylidene)-4-piperidones: A topographical study of some novel potent cytotoxins. Bioorg. Med. Chem. 15, 5854-5865.
3. (a) Schwartz R. E., Helms G. L., Bolessa E. A., Wilson K. E., Giacobbe R. A., Tkacz J. S., Bills G. F., Liesch J. M., Zink D. L., Curotto J. E., Pramanik B., Onishi J. C. (1994) Tetrahedron 50, 1675-1686; (b) Das U., Das S., Bandy B., Stables J. P., Dimmock J. R. (2008) Pramanicin, a novel antimicrobial agent from a fungal fermentation. Bioorg. Med. Chem. 16, 3602-3607; (c) Das M., Molnar J., Barath Z., Bata Z., Dimmock, J. R. (2008) 1-[4-(2-Aminoethoxy)phenylcarbonyl]-3,5-bis-(benzylidene)-4-oxopiperidines: A novel series of highly potent revertants of P-glycoprotein associated multidrug resistance. Bioorg. Med. Chem. Lett. 18, 3484-3487.
4. Coutrot P., Claudel S., Didierjean C., Grison C. (2006) Stereoselective synthesis and glycosidase inhibitory activity of 3,4-dihydroxy-pyrrolidin-2-one-3,4-dihydroxy-piperidin-2-one and 1,2-dihydroxy-pyrrolizidin-3-one. Bioorg. Med. Chem. Lett. 16, 417-420.
5. Baures P. W., Eggleston D. S., Erhard K. F., Cieslinski L. B., Torphy T. J., Christensen S. B. (1993) Crystal structure, absolute configuration, and phosphodiesterase inhibitory activity of (+)-1-(4-bromobenzyl)-4-[(3-cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone. J. Med. Chem. 36, 3274-3277.
6. (a) Ho B., Crider A. M., Stables J. P. (2001) Synthesis and structure–activity relationships of potential anticonvulsants based on 2-piperidine carboxylic acid and related pharmacophores. Eur. J. Med. Chem. 36, 265-286; (b) Le Tiran A., Stables J. P., Kohn H. (2001) Functionalized amino acid anticonvulsants: synthesis and pharmacological evaluation of conformationally restricted analogues. Bioorg. Med. Chem. 9, 2693-2708.
7. Mitchell G., Barnes N. J., Cox J. M., Matthews I. R., Parry D. R., Pearson D. P. J., Smith S. C. (2001) ACS Symposium Series, Vol. 800, Chapter 3, pp 18-29.
8. Rubiralta M., Diez A., Balet A., Bosch J. (1987) New synthesis of benzo[a]quinolizidin-2-ones via protected 2-Aryl-4-piperidones. Tetrahedron 43, 3021-3030.
9. Kumar R. R., Perumal S. (2007) A facile synthesis and highly atom economic 1,3-dipolar cycloaddition of hexahydropyrido[3,4-c][1,5]benzothiazepines with nitrile oxide: Stereoselective formation of hexahydro[1,2,4]oxadiazolo[5,4-d]pyrido[3,4-c][1,5]-benzothiazepines. Tetrahedron 63, 7850-7857.
10. Commins D. L., Ollinger C. G. (2001) Tetrahedron Lett. 42, 4115-4118.
11. Diez A., Voldoire A., Lopez I., Rubiralta M., Segarra V., Pages L., Palacois J. M. (1995) Synthetic applications of 2-aryl-4-piperidones X: Synthesis of 3-aminopiperidines, potential substance P antagonists. Tetrahedron 51, 5143-5156.
12. Rubiralta M., Diez A., Vila C., Bettiol J. L., Troin Y., Sinibaldi M. E. (1992) Synthetic applications of 2-aryl-4-piperidones. VIII: Synthesis of methyl indolo-[2,3-a]quinolizidin-2-acetate. Tetrahedron Lett. 33, 1233-1236.
13. Diez A., Tona M., Rubiralta M. (1990) Synthetic applications of protected 2-aryl-4-piperidones. V. Synthesis of guettardine and 15-epiguettardine. Tetrahedron 46, 4393-4406.
14. Lopez I., Diez A., Rubiralta M. (1996) Synthetic applications of 2-aryl-4-piperidones XI: A new synthesis of the E-azaburnamine skeleton. Tetrahedron 52, 8581-8600.
15. Radisky D. C., Radisky E. S., Barrows L. R., Copp B. R., Kramer R. A., Ireland C. M. (1993) Novel cytotoxic topoisomerase II inhibiting pyrroloiminoquinones from Fijian sponges of the genus Zyzzya. J. Am. Chem. Soc. 115, 1632-1638.
16. Moro-oka Y., Fukuda T., Iwao M. (1999) The first total synthesis of veiutamine, a new type of pyrroloiminoquinone marine alkaloid. Tetrahedron Lett. 40, 1713-1716.
17. Rubiralta M., Marco M. P., Bolos J., Trape J. (1991) Synthetic applications of 2-aryl-4-piperidones. V1: Synthesis of the fundamental tetracyclic skeleton of ervitsine and its 20-deethylidene-6,16-dihydro analogue. Tetrahedron 47, 5585-5602.
18. Hartwig J. F. (1998) Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: Scope and mechanism. Angew. Chem. Int. Ed. 37, 2046-2067.
19. Klapars A., Antilla J. C., Huang X., Buchwald S. L. (2001) A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles. J. Am. Chem. Soc. 123, 7727-7729.
20. Deng W., Wang Y. F., Zou Y., Liu L., Guo Q.-X. (2004) Amino acid-mediated Goldberg reactions between amides and aryl iodides. Tetrahedron Lett. 45, 2311-2315.
21. Klapars A., Huang X., Buchwald S. L. (2002) A general and efficient copper catalyst for the amidation of aryl halides. J. Am. Chem. Soc. 124, 7421-7428.
22. Cai Q., Zhu W., Zhang H., Zhang Y. D., Ma D. W. (2005) Preparation of N-aryl compounds by amino acid-promoted Ullmann-type coupling reactions. Synthesis 496-499.
23. Guo X., Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. (2006) An inexpensive and efficient copper catalyst for N-arylation of amines, amides and nitrogen-containing heterocycles. Adv. Synth. Catal. 348, 2197-2202.
24. Lv X., Bao W.A. (2007) B-Keto ester as a novel, efficient, and versatile ligand for copper (I)-catalyzed C-N, C-O, and C-S coupling reactions. J. Org. Chem. 72, 3863-3867.
25. Kwong F. Y., Klapars A., Buchwald S. L. (2002) Copper-catalyzed coupling of alkylamines and aryl iodides: An efficient system even in an air atmosphere.Org. Lett. 4, 581-584.
26. Yang Y.-H., Shi M. (2005) Ring-expanding reaction of cyclopropyl amides with triphenylphosphine and carbon tetrahalide. J. Org. Chem. 70, 8645-8648.
27. (a) Chaturvedi D., Chaturvedi A. K., Mishra N., Mishra V.(2012) Org. Biomol. Chem. 10, 9148-9151; (b) Chaturvedi D., Chaturvedi A.K., Mishra N., Mishra V. (2012) Synlett 23, 2627-2630.
28. Sankaranarayanan S., Chattopadhyay S. (1998) Asymmetric synthesis of a cytotoxic amide of Telesto riisei. Tetrahedron Assym. 9, 1345-1350.
2. (a) Dimmock J. R., Jha A., Zello G. A., Quail J. W., Oloo E. O., Nienaber K. H., Kowalczyk E. S., Allen T. M., Santos C. L., De Clercq E., Balzarini J., Manavathu E. K., Stables J. P. (2012) Cytotoxic N-[4-(3-aryl-3-oxo-1-propenyl)phenylcarbonyl]-3,5-bis(phenylmethylene)-4-piperidones and related compounds. Eur. J. Med. Chem. 37, 961-972; (b) Jha A., Mukherjee C., Prasad A. K., Parmar V. S., De Clercq E., Balzarini J., Stables J. P., Manavathu E. K., Srivastava A., Sharma R. K., Nienaber K. H., Zello G. A., Dimmock J. R. (2007) E,E,E-1-(4-Arylamino-4-oxo-2-butenoyl)-3,5-bis(arylidene)-4-piperidones: A topographical study of some novel potent cytotoxins. Bioorg. Med. Chem. 15, 5854-5865.
3. (a) Schwartz R. E., Helms G. L., Bolessa E. A., Wilson K. E., Giacobbe R. A., Tkacz J. S., Bills G. F., Liesch J. M., Zink D. L., Curotto J. E., Pramanik B., Onishi J. C. (1994) Tetrahedron 50, 1675-1686; (b) Das U., Das S., Bandy B., Stables J. P., Dimmock J. R. (2008) Pramanicin, a novel antimicrobial agent from a fungal fermentation. Bioorg. Med. Chem. 16, 3602-3607; (c) Das M., Molnar J., Barath Z., Bata Z., Dimmock, J. R. (2008) 1-[4-(2-Aminoethoxy)phenylcarbonyl]-3,5-bis-(benzylidene)-4-oxopiperidines: A novel series of highly potent revertants of P-glycoprotein associated multidrug resistance. Bioorg. Med. Chem. Lett. 18, 3484-3487.
4. Coutrot P., Claudel S., Didierjean C., Grison C. (2006) Stereoselective synthesis and glycosidase inhibitory activity of 3,4-dihydroxy-pyrrolidin-2-one-3,4-dihydroxy-piperidin-2-one and 1,2-dihydroxy-pyrrolizidin-3-one. Bioorg. Med. Chem. Lett. 16, 417-420.
5. Baures P. W., Eggleston D. S., Erhard K. F., Cieslinski L. B., Torphy T. J., Christensen S. B. (1993) Crystal structure, absolute configuration, and phosphodiesterase inhibitory activity of (+)-1-(4-bromobenzyl)-4-[(3-cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone. J. Med. Chem. 36, 3274-3277.
6. (a) Ho B., Crider A. M., Stables J. P. (2001) Synthesis and structure–activity relationships of potential anticonvulsants based on 2-piperidine carboxylic acid and related pharmacophores. Eur. J. Med. Chem. 36, 265-286; (b) Le Tiran A., Stables J. P., Kohn H. (2001) Functionalized amino acid anticonvulsants: synthesis and pharmacological evaluation of conformationally restricted analogues. Bioorg. Med. Chem. 9, 2693-2708.
7. Mitchell G., Barnes N. J., Cox J. M., Matthews I. R., Parry D. R., Pearson D. P. J., Smith S. C. (2001) ACS Symposium Series, Vol. 800, Chapter 3, pp 18-29.
8. Rubiralta M., Diez A., Balet A., Bosch J. (1987) New synthesis of benzo[a]quinolizidin-2-ones via protected 2-Aryl-4-piperidones. Tetrahedron 43, 3021-3030.
9. Kumar R. R., Perumal S. (2007) A facile synthesis and highly atom economic 1,3-dipolar cycloaddition of hexahydropyrido[3,4-c][1,5]benzothiazepines with nitrile oxide: Stereoselective formation of hexahydro[1,2,4]oxadiazolo[5,4-d]pyrido[3,4-c][1,5]-benzothiazepines. Tetrahedron 63, 7850-7857.
10. Commins D. L., Ollinger C. G. (2001) Tetrahedron Lett. 42, 4115-4118.
11. Diez A., Voldoire A., Lopez I., Rubiralta M., Segarra V., Pages L., Palacois J. M. (1995) Synthetic applications of 2-aryl-4-piperidones X: Synthesis of 3-aminopiperidines, potential substance P antagonists. Tetrahedron 51, 5143-5156.
12. Rubiralta M., Diez A., Vila C., Bettiol J. L., Troin Y., Sinibaldi M. E. (1992) Synthetic applications of 2-aryl-4-piperidones. VIII: Synthesis of methyl indolo-[2,3-a]quinolizidin-2-acetate. Tetrahedron Lett. 33, 1233-1236.
13. Diez A., Tona M., Rubiralta M. (1990) Synthetic applications of protected 2-aryl-4-piperidones. V. Synthesis of guettardine and 15-epiguettardine. Tetrahedron 46, 4393-4406.
14. Lopez I., Diez A., Rubiralta M. (1996) Synthetic applications of 2-aryl-4-piperidones XI: A new synthesis of the E-azaburnamine skeleton. Tetrahedron 52, 8581-8600.
15. Radisky D. C., Radisky E. S., Barrows L. R., Copp B. R., Kramer R. A., Ireland C. M. (1993) Novel cytotoxic topoisomerase II inhibiting pyrroloiminoquinones from Fijian sponges of the genus Zyzzya. J. Am. Chem. Soc. 115, 1632-1638.
16. Moro-oka Y., Fukuda T., Iwao M. (1999) The first total synthesis of veiutamine, a new type of pyrroloiminoquinone marine alkaloid. Tetrahedron Lett. 40, 1713-1716.
17. Rubiralta M., Marco M. P., Bolos J., Trape J. (1991) Synthetic applications of 2-aryl-4-piperidones. V1: Synthesis of the fundamental tetracyclic skeleton of ervitsine and its 20-deethylidene-6,16-dihydro analogue. Tetrahedron 47, 5585-5602.
18. Hartwig J. F. (1998) Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: Scope and mechanism. Angew. Chem. Int. Ed. 37, 2046-2067.
19. Klapars A., Antilla J. C., Huang X., Buchwald S. L. (2001) A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles. J. Am. Chem. Soc. 123, 7727-7729.
20. Deng W., Wang Y. F., Zou Y., Liu L., Guo Q.-X. (2004) Amino acid-mediated Goldberg reactions between amides and aryl iodides. Tetrahedron Lett. 45, 2311-2315.
21. Klapars A., Huang X., Buchwald S. L. (2002) A general and efficient copper catalyst for the amidation of aryl halides. J. Am. Chem. Soc. 124, 7421-7428.
22. Cai Q., Zhu W., Zhang H., Zhang Y. D., Ma D. W. (2005) Preparation of N-aryl compounds by amino acid-promoted Ullmann-type coupling reactions. Synthesis 496-499.
23. Guo X., Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. (2006) An inexpensive and efficient copper catalyst for N-arylation of amines, amides and nitrogen-containing heterocycles. Adv. Synth. Catal. 348, 2197-2202.
24. Lv X., Bao W.A. (2007) B-Keto ester as a novel, efficient, and versatile ligand for copper (I)-catalyzed C-N, C-O, and C-S coupling reactions. J. Org. Chem. 72, 3863-3867.
25. Kwong F. Y., Klapars A., Buchwald S. L. (2002) Copper-catalyzed coupling of alkylamines and aryl iodides: An efficient system even in an air atmosphere.Org. Lett. 4, 581-584.
26. Yang Y.-H., Shi M. (2005) Ring-expanding reaction of cyclopropyl amides with triphenylphosphine and carbon tetrahalide. J. Org. Chem. 70, 8645-8648.
27. (a) Chaturvedi D., Chaturvedi A. K., Mishra N., Mishra V.(2012) Org. Biomol. Chem. 10, 9148-9151; (b) Chaturvedi D., Chaturvedi A.K., Mishra N., Mishra V. (2012) Synlett 23, 2627-2630.
28. Sankaranarayanan S., Chattopadhyay S. (1998) Asymmetric synthesis of a cytotoxic amide of Telesto riisei. Tetrahedron Assym. 9, 1345-1350.