Rearrangements of the [2+2]-cycloadducts of DDQ and 2-ethynylpyrroles

Tetrahedron Letters

Volumn 51, Issue 38, 2010, Pages 5028-5031

  Trofimov, Boris A ^a   Sobenina, Lyubov N ^a   Stepanova, Zinaida V ^a   Ushakov, Igor A ^a   Mikhaleva, Albina I ^a   Tomilin, Denis N ^a   Kazheva, Olga N ^b   Alexandrov, Grigorii G ^c   Chekhlov, Anatolii N ^b   Dyachenko, Oleg A ^b  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

^b INSTITUTE OF PROBLEMS OF CHEMICAL PHYSICS   (Russian Federation)

^c KURNAKOV INSTITUTE OF GENERAL AND INORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Bicyclo 3.2.0 heptadienone; Bicyclo 4.2.0 octadienedione; Cyclobutene; Dihydrofuranone; Ethanolysis; Rearrangement

Indexed keywords

2 ETHYNYLPYRROLE; 2,3 DICHLORO 5,6 DICYANO 1,4 BENZOQUINONE; BENZOQUINONE; DIETHYL 3 CHLORO 1,5 DICYANO 4 OXO 7 (4,5,6,7 TETRAHYDRO 1H INDOL 2 YL)BICYCLO[3.2.0]HEPTA 2,6 DIENE 2,6 DICARBOXYLATE; ETHYL 3,4 DICYANO 4 (3,4 DICHLORO 2 ETHOXY 5 OXO 2,5 DIHYDRO 2 FURANYL) 2 (4,5,6,7 TETRAHYDRO 1H INDOL 2 YL) 1 CYCLOBUTENE 1 CARBOXYLATE; ETHYL 6 BENZOYL 3 CHLORO 6 1,5 DICYANO 4 OXO 7 (4,5,6,7 TETRAHYDRO 1H INDOL 2 YL) BICYCLO[3.2.0]HEPTA 2,6 DIENE 2 CARBOXYLATE; ETHYL 7 BENZOYL 3 CHLORO 6 [5 (4 CHLOROPHENYL) 1H PYRROL 2 YL] 1,5 DICYANO 4 OXOBICYCLO[3.2.0]HEPTA 2,6 DIENE 2 CARBOXYLATE; ETHYL 7 BENZOYL 3 CHLORO 6 [5 PHENYL] 1H PYRROL 2 YL] 1,5 DICYANO 4 OXOBICYCLO [3.2.0]HEPTA 2,6 DIENE 2 CARBOXYLATE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 78649331333     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.100     Document Type: Article

References (20)

1. Trofimov, B. A.; Sobenina, L. N.; Stepanova, Z. V.; Ushakov, I. A.; Sinegovskaya, L. M.; Vakul'skaya, T. I.; Mikhaleva, A. I. Synthesis 2010, 470-477.
2. Trofimov, B. A.; Stepanova, Z. V.; Sobenina, L. N.; Mikhaleva, A. I.; Ushakov, I. A. Tetrahedron Lett. 2004, 45, 6513-6516;
3. Trofimov, B. A.; Sobenina, L. N.; Stepanova, Z. V.; Petrova, O. V.; Ushakov, I. A.; Mikhaleva, A. I. Tetrahedron Lett. 2008, 49, 3946-3949.
4. 4
5. 5 (Fig. 2), taking a general position. The cyclobutene fragment is almost planar, maximum atom deviation from the averaged plane did not exceed 0.002 Å. In the fragment, one of a longest ordinary C-C bond 1.62(1) Å was detected. The dihedral angles formed by the cyclobutene plane and cyano substituents are 53.4° and 71.1°, respectively. The angle between the cyclobutene moiety and the average plane of the ester unit is 172.0°. The pyrrole fragment has analmost planar structure, themaximumdeviationof atoms from its plane being 0.01 Å. The dihedral angle between the cyclobutene and pyrrole planes equals 173.4°. The dihydrofuranone substituent is also almost planar, themaximumdeviation of atoms fromits plane being 0.01 Å. The dihedral angle formed by this fragment with the cyclobutene plane is 63.1°. The angle between the ethoxy group and the furan fragment is 82.5°.
6. Pappas, S. P.; Pappas, B. S.; Portnoy, N. A. J. Org. Chem. 1969, 34, 520-525.
7. Knunyants, I. L.; Rozhkov, I. N.; Stepanov, A. A.; Antipin, M. Y.; Kravers, M. A.; Struchkov, Y. T. Dokl. Akad. Nauk SSSR 1979, 248, 1128-1131;
8. Bagryanskaya, I. Y.; Gatilov, Y. V.; Osadchii, S. A. Russ. Zh. Strukt. Khim. 1984, 25, 178-180;
9. Armesto, D.; Albert, A.; Cano, F. H.; Martin, N.; Ramos, A.; Rodriguez, M.; Segura, J. L.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1997, 3401-3405;
10. Yeh, W.-Y.; Liu, Y.-C.; Peng, S.-M.; Lee, G.-H. Organometallics 2003, 22, 2361-2363;
11. Liu, Y.; Liu, M.; Song, Z. J. Am. Chem. Soc. 2005, 127, 3662-3663.
12. Carlton, J. B.; Levin, R. H.; Clardy, J. J. Am. Chem. Soc. 1976, 98, 6068-6070;
13. Schnapp, K. A.; Motz, P. L.; Stoeckel, S. M.; Wilson, R. M.; Bauer, J. A. K.; Bohne, C. Tetrahedron Lett. 1996, 37, 2317-2320;
14. Wu, H.-P.; Aumann, R.; Frohlich, R.; Wibbeling, B. Eur. J. Org. Chem. 2000, 1183-1192;
15. Wu, H.-P.; Aumann, R.; Venne-Dunker, S.; Saarenketo, P. Eur. J. Org. Chem. 2000, 3463- 3473;
16. Wu, H.-P.; Aumann, R.; Frohlich, R.; Saarenketo, P. Chem. Eur. J. 2001, 7, 700-710.
17. Baudouy, R.; Crabbe, P.; Greene, A. E.; Le Drain, C.; Orr, A. F. Tetrahedron Lett. 1977, 34, 2973-2976;
18. Gibson, S. E.; Mainolfi, N.; Kalindijan, S. B.; Wright, P. T. Angew. Chem., Int. Ed. 2004, 43, 5680-5682.
19. Pandya, B. A. Boston College Dissertations and Theses. Paper AAI3283895, 2007.
20. Sheldrick, G. M. SHELXS 97, SHELXL 97; University of Gottingen: Germany, 1997.