New compounds in ring-opening reaction of 5-substituted epoxyisoindolines
Corresponding Author
Ana Dunja Mance
Faculty of Chemical Engineering and Technology of the University of Zagreb, Department of Organic Chemistry, Marulićev trg 20, HR 10000, Zagreb, Croatia
Faculty of Chemical Engineering and Technology of the University of Zagreb, Department of Organic Chemistry, Marulićev trg 20, HR 10000, Zagreb, CroatiaSearch for more papers by this authorBranko Borovička
Faculty of Chemical Engineering and Technology of the University of Zagreb, Department of Organic Chemistry, Marulićev trg 20, HR 10000, Zagreb, Croatia
Search for more papers by this authorKreŠImir Jakopčić
Faculty of Chemical Engineering and Technology of the University of Zagreb, Department of Organic Chemistry, Marulićev trg 20, HR 10000, Zagreb, Croatia
Search for more papers by this authorGordana Pavlović
Faculty of Science of the University of Zagreb, Chemistry Department, Laboratory for General and Inorganic Chemistry, Kralja Zvonimira 8, HR 10000, Zagreb, Croatia
Search for more papers by this authorIvan Leban
Faculty of Chemistry and Chemical Technology of the University of Ljubljana, Laboratory of Inorganic Chemistry, P.O. Box 537, 1001, Ljubljana, Slovenia
Search for more papers by this authorCorresponding Author
Ana Dunja Mance
Faculty of Chemical Engineering and Technology of the University of Zagreb, Department of Organic Chemistry, Marulićev trg 20, HR 10000, Zagreb, Croatia
Faculty of Chemical Engineering and Technology of the University of Zagreb, Department of Organic Chemistry, Marulićev trg 20, HR 10000, Zagreb, CroatiaSearch for more papers by this authorBranko Borovička
Faculty of Chemical Engineering and Technology of the University of Zagreb, Department of Organic Chemistry, Marulićev trg 20, HR 10000, Zagreb, Croatia
Search for more papers by this authorKreŠImir Jakopčić
Faculty of Chemical Engineering and Technology of the University of Zagreb, Department of Organic Chemistry, Marulićev trg 20, HR 10000, Zagreb, Croatia
Search for more papers by this authorGordana Pavlović
Faculty of Science of the University of Zagreb, Chemistry Department, Laboratory for General and Inorganic Chemistry, Kralja Zvonimira 8, HR 10000, Zagreb, Croatia
Search for more papers by this authorIvan Leban
Faculty of Chemistry and Chemical Technology of the University of Ljubljana, Laboratory of Inorganic Chemistry, P.O. Box 537, 1001, Ljubljana, Slovenia
Search for more papers by this authorAbstract
Methoxy or nitro group present in the furan ring of tertiary alkenylfurfurylamine changes the expected results of both, the intramolecular [4+2]cycloaddition and the acid catalyzed ring-opening reaction of the derived oxatricycloadduct. With a 5-methoxy group, in addition to the expected 5-methoxyisoindoline 3, the corresponding hydroxy derivative 5 was obtained. On the other hand a 5-nitro group changes the outcome of the reaction even more profoundly. Instead of the expected 5-nitroisoindoline 12, 5-nitro-substituted epoxy-isoindoline 6 submitted to ring-opening reaction with the mixture of hydrobromic and acetic acid, yielded the mixture of bromo-substituted epoxy compounds 7,8, 9 and/or bromo-substituted isoindolines 10 and 11.
References and Notes
- 1 The acronym widely used since late eighties. See e.g.: C. Rogers and B. A. Keay, Tetrahedron Lett., 30, 1349–1352 (1989).
- 2a
For a review about intramolecular Diels-Alder (IMDA) and intramolecular Diels-Alder reaction with furan diene (IMDAF) see e.g.:
A. G. Fallis,
Can. J, Chem.,
77,
159
(1999);
2b
O. C. Kappe,
Sh. S. Murphree and
A. Padwa,
Tetrahedron,
53,
14179
(1997);
2c
T. Hudlicky,
G. Butora,
S. P. Fearnley,
A. G. Gum,
P. J. Persichini III,
M. R. Stabile and
J. S. Merola,
J. Chem. Soc., Perkin. Trans.,
I,
2393
(1995);
2d
W. Carruthers,
Cyclization Reactions in Organic Synthesis,
Pergamon Press, Oxford,
1990;
2e
D. Craig,
Chem. Soc. Rev.,
16,
187
(1987);
2f
B. H. Lipschutz,
Chem. Rev.,
86,
795
(1986);
2g
D. F. Taber,
Intramolecular Diels-Alder Reactions and Alder Ene Reaction,
Springer Verlag, New York,
1984;
10.1007/978-3-642-69233-8 Google Scholar2h A. G. Fallis, Can. J. Chem., 62, 183 (1984); 2i E. Ciganek, Organic Reactions, Vol. 32, W. G. Dauben, ed., John Wiley and Sons, Inc., New York, 1984, p. 1–374; 2j G. Brieger and J. Bennett, Chem. Rev., 80, 63 (1980); 2k W. Oppolzer, Angew. Chem., Int. Ed. Engl., 16, 10 (1977).
- 3 A. D. Mance, B. Borovička, B. Karaman and K. Jakopčić, J. Heterocyclic Chem., 36, 1337 (1999).
- 4 A. D. Mance M. Šindler-Kulyk, K. Jakopčić, A. Hergold-Brundić and A. Nagl, J. Heterocyclic Chem., 34, 1315 (1997) and preceding papers cited therein.
- 5 For a review see e.g.: R. Fikentscher, H. Kröper and J. Sand, in Methoden der organischen Chemie (Houben-Weil), Band VI, Teil 4, E. Müller, ed., Georg Thieme Verlag, Stuttgart, 1966, p. 670–674.
- 6a
D. Bilović,
Ž. Stojanac and
V. Hahn,
Tetrahedron Lett.,
1964,
2071
(1964),
10.1016/S0040-4039(01)89456-9 Google Scholar6b D. Bilović and V. Hahn, Croat. Chem. Acta, 39, 189 (1967).10.1016/S0003-2670(01)80480-3 Google Scholar
- 7a Ž. Klepo and K. Jakopčić, Croat. Chem. Acta, 47, 45 (1975); 7b Ž. Klepo and K. Jakopčić, J. Heterocyclic Chem., 24, 1787 (1987); 7c A. D. Mance and K. Jakopčić, Vestn. Slov. Kem. Društ., 33, 287 (1986); 7d A. D. Mance, K. Jakopčć and M. Šindler-Kulyk, Synthetic Commun., 26, 923 (1996); 7e A. D. Mance M. Šindler-Kulyk, K. Jakopčić, A. Hergold-Brundić and A. Nagl, J. Heterocyclic Chem., 34, 1315 (1997).
- 8a See e.g.: A. Padwa, M. A. Brodney, K. Satake and C. S. Straub, J. Org. Chem., 64, 4617 (1999); 8b A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem., 64, 3595 (1999); 8c B. J. McNelis, J. T. Starr and Hung Dang, J. Heterocyclic Chem., 35, 1509 (1998); 8d S. Woo, M. Parvez, B. A. Keay, Can. J. Chem., 75, 665 (1997); 8e D. Prapajapati and J. S. Sandhu, Heterocycles, 23, 17 (1985); 8f R. S. Mkrtchyan, G. O. Torosyan, K. Ts. Tagmazyan and A. T. Babayan, Arm. Khim. Zh., 31, 328 (1978).
- 9 As a matter of fact such a possibility was indicated in the early papers from this laboratory [6].
- 10 The formation of 2b was indicated by 1H nmr spectra in the experiment with deuteriochloroform solution of 1b standing at -18 °C for several months.
- 11 A. L. Spek, PLATON98 for Windows, University of Utrecht, The Netherlands (1998).
- 12 Probably under participation of oxygen from air and an amine present in the reaction mixture [13].
- 13a
For a review about bromination see e.g.:
Y. Sasson,
“ Formation of carbon-halogen bonds (Cl, Br, I)” in
Suplement D2:
The chemistry of halides pseudohalides and azides,
S. Patai and
Z. Rappoport, Ed's,
J. Wiley and Sons, New York,
1995,
p. 535;
10.1002/047002349X.ch11 Google Scholar13b B. C. Challis and A. R. Butler, “ Substitution at an amino nitrogen” in The chemistry of the amino group, S. Patai, Ed., J. Wiley and Sons, London, 1968, p. 278.
- 14 The rest (70%) was 3a.
- 15 Stoe & Cie, STADI4, Diffractometer Control Program, Darmstadt, Germany (1995).
- 16 Stoe & Cie, X-RED, Data Reduction Program for Windows, Darmstadt, Germany, 1995.
- 17 P. T. Beurskens, G. Beurskens, W. P. Bosman, R. de Gelder, S. Garcia-Granda, R. O. Gould, R. Israel and J. M. M. Smits, The DIRDIF96 program system, Crystallography Laboratory, University of Nijmegen, Netherlands (1998).
- 18 G. M. Sheldrick, SHELXL97, Crystal Structure Refinement Program, University of Göttingen, Germany (1997).
- 19 Resolved by the use of APT technique.
- 20 Z. Otwinowski and W. Minor, Processing of X-ray Diffraction Data Collected in Oscillation Mode in Methods in Enzymology, Vol. 276, Macromolecular Crystallography, part A, edited by C. W. Carter and R. M. Sweet, Academic Press, London (1997) p. 307.
- 21 G. M. Sheldrick, Acta Cryst., A46, 467 (1990)
