Study of regioselectivity of intramolecular cyclization of N-(m-R-phenyl)- and N-(α-naphthyl)-2-allyl(methallyl)-6-carboxy-4-oxo-3-aza-10- oxatricyclo[5.2.1.01,5]dec-8-enes

Russian Chemical Bulletin

Volumn 53, Issue 12, 2004, Pages 2816-2829

  Zubkov, F I ^a   Boltukhina, E V ^a   Nikitina, E V ^a   Varlamov, A V ^a  

^a PEOPLES FRIENDSHIP UNIVERSITY OF RUSSIA   (Russian Federation)

Author keywords

3a,6 epoxyisoindoles; Homoallylamines; Intramolecular 4+2 cycloaddition; Intramolecular Diels Alder reaction; Isoindolo 2,1 a quinolines

Indexed keywords

2 METHYL 5,5 DIMETHYL 5,6,6A,11 TETRAHYDRO 11 OXO 10 CARBOXYISOINDOLO[2,1 A]QUINOLINE; 2 METHYLCHLORO 5 METHYL 5,6,6A,11 TETRAHYDRO 11 OXO 10 CARBOXYISOINDOLO[2,1 A]QUINOLINE; 2 METHYLCHLORO 5,5 DIMETHYL 5,6,6A,11 TETRAHYDRO 11 OXO 10 CARBOXYISOINDOLO[2,1 A]QUINOLINE; 2 METHYLMETHOXY 5 METHYL 5,6,6A,11 TETRAHYDRO 11 OXO 10 CARBOXYISOINDOLO[2,1 A]QUINOLINE; 2 METHYLMETHOXY 5,5 DIMETHYL 5,6,6A,11 TETRAHYDRO 11 OXO 10 CARBOXYISOINDOLO[2,1 A]QUINOLINE; 2,5 DIMETHYL 5,6,6A,11 TETRAHYDRO 11 OXO 10 CARBOXYISOINDOLO[2,1 A]QUINOLINE; 4 METHYL 5,5 DIMETHYL 5,6,6A,11 TETRAHYDRO 11 OXO 10 CARBOXYISOINDOLO[2,1 A]QUINOLINE; 4 METHYLCHLORO 5 METHYL 5,6,6A,11 TETRAHYDRO 11 OXO 10 CARBOXYISOINDOLO[2,1 A]QUINOLINE; 4 METHYLCHLORO 5,5 DIMETHYL 5,6,6A,11 TETRAHYDRO 11 OXO 10 CARBOXYISOINDOLO[2,1 A]QUINOLINE; 4 METHYLMETHOXY 5 METHYL 5,6,6A,11 TETRAHYDRO 11 OXO 10 CARBOXYISOINDOLO[2,1 A]QUINOLINE; 4 METHYLMETHOXY 5,5 DIMETHYL 5,6,6A,11 TETRAHYDRO 11 OXO 10 CARBOXYISOINDOLO[2,1 A]QUINOLINE; 4,5 DIMETHYL 5,6,6A,11 TETRAHYDRO 11 OXO 10 CARBOXYISOINDOLO[2,1 A]QUINOLINE; 7,8,8A,13 TETRAHYDRO 7,7 DIMETHYL 13 OXOBENZ[H]ISOINDOLO[2,1 A]QUINOLINE 12 CARBOXYLIC ACID; ALKENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; NAPHTHYL GROUP; PHENYL GROUP; PHOSPHORIC ACID; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; INFRARED SPECTROSCOPY; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 21644489224     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-005-0196-5     Document Type: Article

References (17)

1. J. Epsztajn, A. Jóźwiak, P. Kołuda, I. Sadokierska, and I. D. Wilkowska, Tetrahedron, 2000, 56, 4837.
2. P. Pigeon and B. Decroix, Synth. Commun., 1998, 28, 2507.
3. Y. Abe, A. Ohsawa, and H. Igeta, Heterocycles, 1982, 19, 49.
4. P. Pigeon, M. Othman, P. Netchitaïlo, and B. Decroix, J. Heterocycl. Chem., 1999, 36, 691.
5. D.-B. Reuschling and F. Krönke, Chem. Ber., 1971, 104, 2103.
6. J. D. White and M. E. Mann, Adv. Heterocycl. Chem., 1969, 10, 113.
7. R. Bonnett and S. A. North, Adv. Heterocycl. Chem., 1981, 29, 341.
8. W. H. N. Nijhuis, G. R. B. Leus, R. J. M. Egberink, W. Verboom, and D. N. Reinhoudt, Recl. Trav. Chim. Pays-Bas, 1989, 108, 172.
9. Y. Ichihara, Y. Kiyota, and G. Goto, Chem. Pharm. Bull., 1990, 38, 3024.
10. Z. Sui, J. Altom, V. N. Nguyen, J. Fernandez, J. I. Bernstein, J. J. Hiliard, J. F. Barrett, B. L. Podlogar, and K. A. Ohemeng, Bioorg. Med. Chem., 1998, 6, 735.
11. A. V. Varlamov, F. I. Zubkov, E. V. Boltukhina, N. V. Sidorenko, and R. S. Borisov, Tetrahedron. Lett., 2003, 44, 3641.
12. V. V. Kuznetsov, A. E. Aliev, and N. S. Prostakov, Khim. Geterotsikl. Soedin., 1994, 73
13. [Chem. Heterocycl. Compd., 1994, 30, 70 (Engl. Transl.)].
14. V. Kouznetsov, N. Öcal, Z. Turgut, F. Zubkov, S. Kaban, and A. Varlamov, Monatsh. Chem., 1998, 129, 671.
15. A. V. Varlamov, E. V. Boltukhina, F. I. Zubkov, N. V. Sidorenko, A. I. Chernyshev, and D. G. Grudinin, Khim. Geterotsikl. Soedin., 2004, 27
16. [Chem. Heterocycl. Compd., 2004, 40, 22 (Engl. Transl.)].
17. D. Bilović, Croat. Chem. Acta, 1968, 40, 15.