Synthesis of new spiro[1,4,2-dioxazole-5,3'-indolin]-2'-ONE by 1,3-dipolar cycloaddition

Synthetic Communications

Volumn 41, Issue 14, 2011, Pages 2096-2102

  Bouhfid, Rachid ^a,b   Joly, Nicolas ^a   Essassi, El Mokhtar ^b   Lequart, Vincent ^a   Massoui, Mohamed ^b   Martin, Patrick ^a  

^a UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

^b FACULTÉ DES SCIENCES   (Morocco)

Author keywords

1,3 dipolar cycloaddition; 1,4,2 dioxazole; Isatin; Isoxazole; Isoxazoline

Indexed keywords

3 (4 METHOXYPHENYL) 6 ([3 (4 METHOXYPHENYL)ISOXAZOL 5 YL]METHYL)SPIRO[1,4,2 DIOXAZOLINE 5,3' INDOLINE] 7 ONE; 3 (4 METHOXYPHENYL) 6 BENZYLSPIRO[1,4,2 DIOXAZOLINE 5,3' INDOLINE] 7 ONE; 3 (4 METHOXYPHENYL) 6 PROP 2 ENYLSPIRO[1,4,2 DIOXAZOLINE 5,3' INDOLINE] 7 ONE; 3 (4 METHOXYPHENYL) 6 PROP 2 YNYLSPIRO[1,4,2 DIOXAZOLINE 5,3' INDOLINE] 7 ONE; 3 (4 METHOXYPHENYL)SPIRO[1,4,2 DIOXAZOLINE 5,3' INDOLINE] 7 ONE; ISATIN DERIVATIVE; N ALLYLINDOLINE 2,3 DIONE; N BENZYLINDOLINE 2,3 DIONE; N PROPARGYLINDOLINE 2,3 DIONE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 79957631932     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.497595     Document Type: Article

References (18)

1. James, M. N. G.; Williams, G. J. B. The molecular and crystal structure of an oxindole alkaloid (6-hydroxy-2'-(2-methylpropyl)-3,3'- spirotetrahydropyrroIidino-oxindole). Can. J. Chem. 1972, 50, 2407-2412.
2. Elderfield, R. C.; Gilman, R. E. Alstonia alkaloids, 11: Alkaloids of alstonia muelleriana. Phytochemistry 1972, 11, 339-343.
3. Jossang, A.; Jossang, P.; Hadi, H. A.; Sevenet, T.; Bodo, B. Horsfiline, an oxindole alkaloid from Horsfieldia superba. J. Org. Chem. 1991, 56, 6527-6530.
4. Cui, C. B.; Kakeya, H.; Okada, G.; Onose, R.; Osada, H. Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus, 1: Taxonomy, fermentation, isolation and biological properties. J. Antibiot. 1996, 49, 527-533. (Pubitemid 26235660)
5. Jain, M.; Khanna, P.; Saxena, A.; Bhagat, S.; Olsen, C. E.; Jain, S. C. Synthesis of some novel bis-spiro[indole-pyrazolinyl-thiazolidine]-2,40-diones. Synth. Commun. 2006, 36, 1863-1872.
6. Piscopo, E.; Diurno, M. V.; Mazzoni, O.; Ciaccio, A. M. Studies on heterocyclic compounds spiroindole-3,2'-thiazolidine derivatives antimicrobial activity of monohalogenated 3'-phenylspiro-3H-indole-3,2'-thiazolidine-2,4'-1H- diones. Bull. Soc. Ital. Biol. Sper. 1990, 66, 1181-1186.
7. Rajopadhye, M.; Popp, F. D. Synthesis and antileukemic activity of spiro[indoline-3,2'- thiazolidine]-2,4'diones. J. Heterocycl. Chem. 1987, 24, 1637-1641.
8. Kornet, M. J.; Thio, A. P. Oxindole-3-spiropyrrolidines and -piperidines: Synthesis and local anesthetic activity. J. Med. Chem. 1976, 19, 892-898.
9. Hershenson, E. M.; Prodan, K. A.; Kochman, R. L.; Bloss, J. L.; Mackerer, C. R. Synthesis of β-spiropyrrolidinoindolines, their binding to glycine receptor, and in vivo biological activity. J. Med. Chem. 1977, 22, 1448-1451. (Pubitemid 8209554)
10. Jain, R.; Bansal, M. A facile synthesis and central nervous system activities of fluorine containing spiro-[3H-indole-3,4'(4H)-pyran]-2(1H)-ones. Pharmazie 1995, 50, 224-225.
11. Kikugawa, K.; Ichino, M. Platelet-aggregation inhibitors, 5: Pyrimidine derivatives, indole derivatives, benzothiophenes, and benzoquinolizine derivatives. Chem. Pharm. Bull. 1973, 21, 1151-1155.
12. Joshi, K. J.; Jain, R.; Chand, P. Indoles with C-3 as spiro atom. Heterocycles 1985, 23, 957-996.
13. Flann, C. J.; Overman, L. E.; Sarkar, A. K. Synthesis of 3-acyl-3-alkyloxindoles. Tetrahedron Lett. 1991, 32, 6993-6996.
14. Bouhfid, R.; Joly, N.; Ohmani, F.; Essassi, E. M.; Lequart, V.; Banoub, J.; Kheddid, K.; Charof, R.; Massoui, M.; Martin, P. Synthesis and antibacterial activity of new (2,3-dioxo-indolin-1-yl) acetamides. Lett. Org. Chem. 2008, 5, 3-7.
15. Bouhfid, R.; Joly, N.; Massoui, M.; Cecchelli, R.; Lequart, V.; Martin, P.; Essassi, E. M. An efficient synthesis of new spiro[indolo-3(1H),2'(3'H)- oxadiazolyl] and 1-(triazol-4- ylmethyl)isatin derivatives. Heterocycles 2005, 65, 2949-2955.
16. Nyerges, M.; Gajdics, L.; Szollosy, A.; Toke, L. 2-Oxoindolin-3-ylidene derivatives as 2 pi components in 1,3-dipolar cycloadditions of azomethine ylides. Synlett 1999, 1, 111-113. (Pubitemid 29093081)
17. Malinakova, H. C.; Liebeskind, L. S. Enantiocontrolled synthesis of spirooxindoles based on the [5+2] cycloaddition of a Tp(CO)(2)Mo(pyridinyl) scaffold (Tp=hydridotrispyraotrispyrazolylborate). Org. Lett. 2000, 2, 4083-4086.
18. Cecchelli, R.; Dehouck, B.; Descamps, L.; Fenart, L.; Buée-Scherrer, V.; Duhem, C.; Rentfel, M.; Torpier, G.; Dehouck, M. P. In vitro model for evaluating drug transport across the blood-brain barrier. Adv. Drug Delivery Rev. 1999, 36, 165-178. (Pubitemid 29121970)