Rapid and efficient ultrasound-assisted method for the combinatorial synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives

ACS Combinatorial Science

Volumn 14, Issue 1, 2012, Pages 38-43

  Zou, Yi ^a,b   Hu, Yu ^a   Liu, Hai ^a   Shi, Daqing ^a  

^a SOOCHOW UNIVERSITY   (China)

^b JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

Combinatorial synthesis; heterocycle; multicomponent reaction; spiroindoline; ultrasound irradiation

Indexed keywords

INDOLE DERIVATIVE; PYRAZOLE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; SOUND; SYNTHESIS; TIME;

COMBINATORIAL CHEMISTRY TECHNIQUES; INDOLES; MOLECULAR STRUCTURE; PYRAZOLES; SOUND; SPIRO COMPOUNDS; TIME FACTORS;

EID: 84862908792     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co200128k     Document Type: Article

References (52)

1. Cintas, P.; Luche, J. L. Green chemistry. The sonochemical approach Green Chem. 1999, 1, 115-125
2. Li, J. T.; Yin, Y.; Sun, M. X. An efficient one-pot synthesis of 2,3-epoxyl-1,3-diaryl-1-propanone directly from acetophenones and aromatic aldehydes under ultrasound irradiation Ultrason. Sonochem. 2010, 17, 363-366
3. Li, J. T.; Wang, S. X.; Chen, G. F.; Li, T. S. Some application of ultrasound irradiation in organic synthesis Curr. Org. Synth. 2005, 2, 415-436
4. Mamaghani, M.; Dastmard, S. An efficient ultrasound-promoted synthesis of the Baylis-Hillman adducts catalyzed by imidazole and L-proline Ultrason. Sonochem. 2009, 16, 445-447
5. Saleh, T. S.; El-Rahman, N. M. A. Ultrasound promoted synthesis of substituted pyrazoles and isoxazoles containing Sulphone moiety Ultrason. Sonochem. 2009, 16, 237-242
6. Cella, R.; Stefani, H. A. Ultrasound in heterocycles chemistry Tetrahedron 2009, 65, 2619-2641
7. Dömling, A.; Ugi, I. Multicomponent reactions with isocyanides Angew. Chem., Int. Ed. 2000, 39, 3168-3210
8. Dömling, A. Recent developments in Isocyanide based multicomponent reactions in applied chemistry Chem. Rev. 2006, 106, 17-89 (Pubitemid 43159621)
9. Zhu, J.; Bienaymé, H. Multicomponent Reactions; Wiley-VCH: Weinheim, Germany, 2005
10. Dou, G. L.; Shi, C. L.; Shi, D. Q. Highly regioselective synthesis of polysubstituted pyrroles through three-component reaction induced by low-valent titanium reagent J. Comb. Chem. 2008, 10, 810-813
11. Wu, H.; Lin, W.; Wan, Y.; Xin, H. Q.; Shi, D. Q.; Shi, Y. H.; Yuan, R.; Bo, R. C.; Yin, W. Silica gel-catalyzed one-pot synthesis in water and fluorescence properties studies of 5-amino-2-aryl-3 H -chromeno[4,3,2- de ][1,6]naphthyridine-4-carbonitriles and 5-amino-2- aryl-3 H -quinolino[4,3,2- de ][1,6]naphthyridine-4-carbonitriles J. Comb. Chem. 2010, 12, 31-34
12. Houlihan, W. J.; Remers, W. A.; Brown, R. K. Indoles: Part I; Wiley: New York, 1992.
13. Sundberg, R. J. The Chemistry of Indoles; Academic: New York, 1996.
14. Da-Silva, J. F. M.; Garden, S. J.; Pinto, A. C. The chemistry of isatins: a review from 1975 to 1999 J. Braz. Chem. Soc. 2001, 12, 273-324
15. Joshi, K. C.; Chand, P. Biologically active indole derivatives Pharmazie 1982, 37, 1-12 (Pubitemid 12113974)
16. Joshi, K. C.; Jain, R.; Sharma, K.; Bhattacharya, S. K.; Goel, R. K. Studies in spiro-heterocycles. Part-XII. Synthesis of some fluorine containing spiro[3 H -indole-3,4(4 H)-pyrano[2,3- d ]pyrimidine]-2,5,7(1 H)-triones as CNS agents J. Indian Chem. Soc. 1988, 115, 202-204
17. Abdel-Rahman, A. H.; Keshk, E. M.; Hanna, M. A.; El-Bady, S. M. Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents Bioorg. Med. Chem. 2004, 12, 2483-2488 (Pubitemid 38471731)
18. Dandia, A.; Singh, R.; Khaturia, S.; Merienne, C.; Morgant, G.; Loupy, A. Efficient microwave enhanced regioselective synthesis of a series of benzimidazoly/triazolyl spiro [indole-thiazolidinones] as potent antifungal agents and crystal structure of spiro[3 H-indole-3,2′-triazolidine]- 3′(1,2,4-triazol-3-yl)-2,4′(1 H)-dione Bioorg. Med. Chem. 2006, 14, 2409-2417 (Pubitemid 43254748)
19. Khafagy, M. M.; El-Wahas, A. H. F. A.; Eid, F. A.; El-Agrody, A. M. Synthesis of halogen derivatives of benzo[ h ]chromene and benzo[ a ]anthracene with promising antimicrobial activities Farmaco 2002, 57, 715-722 (Pubitemid 35287005)
20. Sebahar, P. R.; Williams, R. M. The asymmetric total synthesis of (+) and (-)-spirotryprostatin B J. Am. Chem. Soc. 2000, 122, 5666-5667
21. Ma, J.; Hecht, S. M. Javaniside, a novel DNA cleavage agent from Alangium javanicum having an unusual oxindole skeleton Chem. Commun. 2004, 1190-1191 (Pubitemid 38797468)
22. Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzinol, L.; Rosen, N. Total synthesis of Spirotryprostatin A, leading to the discovery of some biologically promising analogues J. Am. Chem. Soc. 1999, 121, 2147-2155
23. 2 receptors expressed in xenopus oocyte Eur. J. Pharmacol. 2002, 444, 39-45 (Pubitemid 34621332)
24. Bazgir, A.; Tisseh, Z. N.; Mirzaei, P. An efficient synthesis of spiro[dibenzo[ b, i ] xanthene-1,3,3′-indoline]-pentaones and 5 H -dibenzo[ b, i ]xanthene-tetraones Tetrahedron Lett. 2008, 49, 5165-5168
25. Jadidi, K.; Ghahremanzadeh, R.; Bazgir, A. Spirooxindoles: reaction of 2,6-diaminopyrimidin-4(3 H)-one and isatins Tetrahedron 2009, 65, 2005-2009
26. Dabiri, M.; Azimi, S. C.; Khavasi, H. R.; Bazgir, A. A novel reaction of 6-amino-uracils and isatins Tetrahedron 2008, 64, 7307-7311
27. Jadidi, K.; Ghahremanzadeh, R.; Bazgir, A. Efficient synthesis of spiro[chromeno[2,3- d ]pyrimidine-5,3′-indoline]-tetraones by a one-pot and three-component reaction J. Comb. Chem. 2009, 11, 341-344
28. Ghahremanzadeh, R.; Sayyafi, M.; Ahadi, S.; Bazgir, A. Novel one-pot, three-component synthesis of spiro [indoline-pyrazolo[4′,3′:5,6] pyrido[2,3- d ]pyrimidine]trione library J. Comb. Chem. 2009, 11, 393-396
29. Wang, L. M.; Jiao, N.; Qiu, J.; Yu, J. J.; Liu, J. Q.; Guo, F. L.; Liu, Y. Sodium stearate-catalyzed multicomponent reactions for efficient synthesis of spirooxindoles in aqueous micellar media Tetrahedron 2010, 66, 339-343
30. El-Tamany, E. H.; El-Shahed, F. A.; Mohamed, B. H. Synthesis and biological activity of some pyrazole derivatives J. Serb. Chem. Soc. 1999, 64, 9-18
31. Zaki, M. E. A.; Soliman, H. A.; Hiekal, O. A.; Rashad, A. E. Pyrazolopyranopyrimidines as a class of anti-inflammatory agents Z. Naturforsch. 2006, 61, 1-5
32. Abdelrazek, F. M.; Metz, P.; Metwally, N. H.; El-Mahrouky, S. F. Synthesis and molluscicidal activity of new cinnoline and pyrano[2,3- c ]pyrazole derivatives Arch. Pharm. 2006, 339, 456-460 (Pubitemid 44320225)
33. Abdelrazek, F. M.; Metz, P.; Kataeva, O.; Jaeger, A.; El-Mahrouky, S. F. Synthesis and molluscicidal activity of new chromene and pyrano[2,3- c ]pyrazole derivatives Arch. Pharm. 2007, 340, 543-548 (Pubitemid 350007052)
34. Foloppe, N.; Fisher, L. M.; Howes, R.; Potter, A.; Robertson, A. G. S.; Surgenor, A. E. Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening Bioorg. Med. Chem. 2006, 14, 4792-4802
35. Litvinov, Y. M.; Shestopalov, A. A.; Rodinovskaya, L. A.; Shestopalov, A. M. New convenient four-component synthesis of 6-amino-2,4-dihydropyrano[2,3- c ]pyrazol-5- carbonitriles and one-pot synthesis of 6′-aminospiro[(3 H)-indol-3,4′-pyrano[2,3- c ] pyrazol]-(1 H)-2-one-5′-carbonitriles J. Comb. Chem. 2009, 11, 914-919
36. Zou, Y.; Wu, H.; Hu, Y.; Liu, H.; Zhao, X.; Ji, H. L.; Shi, D. Q. A novel and environment-frienfly method for preparing dihydropyrano[2,3- c ]pyrazoles in water under ultrasound irradiation Ultrason. Sonochem. 2011, 18, 708-712
37. Wang, H. Y.; Zou, Y.; Zhao, X.; Shi, D. Q. A novel and convenient synthesis of 4-hydroxy-6-methyl-3-(1-(phenylimino)ethyl)-2 H -pyran-2-one derivatives under ultrasound irradiation Ultrason. Sonochem. 2011, 18, 1048-1051
38. Liu, H.; Dou, G. L.; Shi, D. Q. Regio- and stereo-selective synthesis of novel dispiropyrrolidine bisoxindole derivatives via multicomponent reactions J. Comb. Chem. 2010, 12, 292-294
39. Liu, H.; Dou, G. L.; Shi, D. Q. Regioselective synthesis of novel spiropyrrolidinesand spirothiapyrrolizidines through multicomponent 1,3-dipolar cycloaddition reaction of azomethine ylides J. Comb. Chem. 2010, 12, 633-637
40. Li, Y. L.; Chen, H.; Shi, C. L.; Shi, D. Q.; Ji, S. J. Efficient one-pot synthesis of spirooxindole derivatives catalyzed by L -proline in aqueous medium J. Comb. Chem. 2010, 12, 231-237
41. Chen, H.; Shi., D. Q. Efficient one-pot synthesis of novel spirooxindole derivatives via three-component reaction in aqueous medium J. Comb. Chem. 2010, 12, 571-576
42. 2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions Tetrahedron 2001, 57, 9509-9511 (Pubitemid 33016767)
43. Mason, T. J.; Peters, D. Practical Sonochemistry, 2 nd ed.; Ellis Horwood: London, U.K., 2002.
44. Dahlem, O.; Reisse, J.; Halloin, V. The radially vibrating horn: A scaling-up possibility for sonochemical reactions Chem. Eng. Sci. 1999, 54, 2829-2838 (Pubitemid 29401150)
45. Li, J. T.; Zhai, X. L.; Chen, G. F. Ultrasound promoted one-pot synthesis of 3-aza-6,10-diaryl-2-oxa-spiro[4.5]decane-1,4,8-trione Ultrason. Sonochem. 2010, 17, 356-358
46. Abd El-Latif, F. F.; Gohar, A. E. M. N.; Fahmy, A. M.; Badr, M. Z. A. Novel synthesis of furo[2,3- b ]indole derivatives Bull. Chem. Soc. Jpn. 1986, 59, 1235-1238
47. Liu, Y.; Zhou, D.; Ren, Z. J.; Cao, W. G.; Chen, J.; Deng, H. M.; Gu, Q. A green efficient synthesis of spiro[indoline-3,4′(1 H ′)-pyrano[2,3- c ]pyrazol]-2-one derivatives J. Chem. Res. 2009, 154-156
48. Redkin, R. G.; Shemchuk, L. A.; Chernykh, V. P.; Shishkin, O. V.; Shishkina, S. V. Synthesis and molecular structure of spirocyclic 2-oxindole derivatives of 2-amino-4 H -pyran condensed with the pyrazolic nucleus Tetrahedron 2007, 63, 11444-11450 (Pubitemid 47498464)
49. Elinson, M. N.; Dorofeev, A. S.; Miloserdov, F. M.; Nikishin, G. I. Electrocatalytic multicomponent assembling of isatins, 3-methyl-2-pyrazolin-5- ones and malononitrile: facile and convenient way to functionalized spirocyclic [indole-3,4′-pyrano[2,3- c ]pyrazole] system Mol. Diversity 2009, 13, 47-52
50. 2AlCN using amino alcohols and BINOLs as catalysts Chem. Commun. 2010, 46, 4330-4332
51. 2AlCN for asymmetric catalytic Strecker reaction J. Org. Chem. 2010, 75, 5144-5150
52. Kaur, P.; Wever, W.; Pindi, S.; Milles, R.; Gu, P.; Shi, M.; Li, G. The GAP chemistry for chiral N -phosphonyl imine-based Strecker reaction Green Chem. 2011, 13, 1288-1292