Ring transformations of heterocyclic compounds. XXIV [1]. 1′,2′,5′,6′-tetrahydro-4′H-spiro[cyclohexa-2, 4-diene-1,2′-pyrrolo[3,2,1-ij]quinoline] and 1,2,4,5,6,7- hexahydrospiro[azepino[3,2,1-hi]indole-2,1′-cyclo-hexa[2,4]diene] - Two new spiro[cyclohexadiene-azaheterocycles] easily accessible by pyrylium ring transformation

Journal of Heterocyclic Chemistry

Volumn 41, Issue 5, 2004, Pages 691-695

  Zimmermann, Thomas ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1',2',5',6' TETRAHYDRO 4'H SPIRO(CYCLOHEXA 2,4 DIENE 1,2' PYRROLO[3,2,1 IJ]QUINOLINE); 1,2,4,5,6,7 HEXAHYDROSPIRO(AZEPINO[3,2,1 HI]INDOLE 2,1' CYCLOHEXA 2,4 DIENE); 2 METHYL 1,4,5,6 TETRAHYDROPYRROLO[3,2,1 IF]QUINOLINIUM PERCHLORATE; 2 METHYL 4,5,6,7 TETRAHYDRO 1H AZEPINO[3,2,1 HI]INDOLIUM PERCHLORATE; 2 METHYLENE 1,2,4,5 TETRAHYDROPYRROLO[3,2,1 HI]INDOLE; 2 METHYLENE 1,2,4,5,6,7 HEXAHYDROAZEPINO[3,2,1 HI]INDOLE; 2 METHYLENE 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLINE; 2 METHYLENEINDOLINE; 4 METHYL 2,5 DIHYDRO 1H PYRROLO[3,2,1 HI]INDOLIUM PERCHLORATE; ACETIC ACID; ALCOHOL; BENZENE; CARBON; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; NITROGEN; PERCHLORATE; PYRYLIUM DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HEATING; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 6344257024     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570410506     Document Type: Article

References (22)

1. Part XXIII: T. Zimmermann and O. Brede, J. Heterocyclic Chem., 39, 263 (2002).
2. T. Zimmermann and M. Pink, J. Prakt. Chem./Chem.-Ztg., 337, 368 (1995).
3. [3a] A. T. Balaban, A. Dinculescu, G. N. Dorofeenko, G. W. Fischer, A. V. Koblik, V. V. Mezheritskii and W. Schroth, Pyrylium Salts. Syntheses, Reactions and Physical Properties, Advances in Heterocyclic Chemistry, Suppl 2, Academic Press, New York, 1982;
4. [b] W. Schroth, W. Dolling and A. T. Balaban, in Houben-Weyl, Vol E7b, R. P. Kreher, ed, Thieme, Stuttgart, 1992, pp 755-1014.
5. 2, R. P. Kreher, ed, Thieme, Stuttgart, 1994, pp 546-1354.
6. [5a] O. Brede, L. Goebel and T. Zimmermann, J. Inf. Rec. Mater., 22, 397 (1996);
7. [b] L. Goebel, O. Brede and T. Zimmermann, Radiat. Phys. Chem., 47, 369 (1996);
8. [c] O. Brede, L. Goebel and T. Zimmermann, J. Phys. Chem. A, 101, 4103 (1997);
9. [d] T. Häupl, T. Zimmermann, R. Hermann and O. Brede, Chem. Phys. Lett., 291, 215 (1998); T. Häupl, T. Zimmermann, R. Hermann and O. Brede, J. Phys. Chem. A, 103, 6904 (1999).
10. [d] T. Häupl, T. Zimmermann, R. Hermann and O. Brede, Chem. Phys. Lett., 291, 215 (1998); T. Häupl, T. Zimmermann, R. Hermann and O. Brede, J. Phys. Chem. A, 103, 6904 (1999).
11. T. Zimmermann and U. Abram, J. Heterocyclic Chem., 37, 1223 (2000).
12. T. Zimmermann, J. Heterocyclic Chem., 37, 885 (2000).
13. T. Zimmermann, J. Heterocyclic Chem., 39, 255 (2002).
14. The formula scheme shows only one enantiomer of the racemate.
15. A detailed description of the reaction sequence is given in ref [2].
16. For the classification of pyrylium ring transformations see ref [3a].
17. A. T. Balaban and C. Toma, Tetrahedron, Supplement 7, 1 (1966).
18. A. Mistr, M. Vavra, J. Skoupy and R. Zahradnik, Collect. Czech. Chem. Commun., 37, 1520 (1972).
19. K. Dimroth, C. Reichardt, T. Siepmann and F. Bohlmann, Liebigs Ann. Chem., 661, 1 (1963).
20. G. N. Dorofeenko, S. V. Krivun and V. V. Mezheritskii, Zh. Obshch. Khim., 35, 632 (1963).
21. G. W. Fischer and M. Hermann, J. Prakt. Chem., 326, 287 (1984).
22. T. Zimmermann, J. Heterocyclic Chem., 41, 103 (2004).