Vicinal dianions of diethyl α-aroylsuccinates: A general synthetic route to α-aroyl- and α-arylidene-γ-butyrolactones

Tetrahedron Letters

Volumn 44, Issue 35, 2003, Pages 6717-6720

  Pohmakotr, Manat ^a   Sampaongoen, Laddawan ^a   Issaree, Arisara ^a   Tuchinda, Patoomratana ^a   Reutrakul, Vichai ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

Author keywords

Dianions; Diethyl aroylsuccinates; aroyl butyrolactones; arylidene butyrolactones

Indexed keywords

ANION; CARBONYL DERIVATIVE; LACTONE DERIVATIVE; METHANE; METHANESULFONYL CHLORIDE; PYRIDINE; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ELIMINATION REACTION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0043172234     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01622-8     Document Type: Article

References (28)

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8. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
9. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
10. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
11. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
12. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
13. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
14. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
15. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
16. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
17. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
18. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
19. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
20. For some recent syntheses, see: (a) Reddy, G. S.; Neelakantan, P.; Iyengar, D. S.; Synth. Commun. 2002, 32, 2601-2604; (b) Mali, R. S.; Babu, K. N. Helv. Chim. Acta 2002, 85, 3525-2530; (c) Consorti, C.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753-755; (d) Grigg, R.; Savic, V. Chem. Commun. 2000, 2381-2382; (e) Jiaang, W.-T.; Wang, C.-L.; Tseng, A.; Chen, S.-T. Heterocycles 2000, 53, 1569-1572; (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L. Synthesis 1997, 1061-1066; (g) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282; (f) Lee, E.; Hur, C.-U.; Jeong, Y.-C.; Rhee, Y.-H.; Chang, M.-H. J. Chem. Soc., Chem. Commun. 1991, 1314-1315; (g) Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Aust. J. Chem. 1988, 41, 251-261; (h) Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641-644; (i) Tanaka, K.; Unema, H.; Yamgishi, N.; Ono, N.; Kaji, A. Chem. Lett. 1978, 653-656; (j) Janecki, T.; Blaszezyk, E. Synthesis 2001, 403-408; (k) Castulik, J.; Mazal, C. Tetrahedron Lett. 2001, 41, 2741-2744.
21. 10.
22. Irradiation of H-4 resulted in 7.9% enhancement of H-5, but there was no effect on H-3. The enhancement of 8.5% of H-4 was observed, when H-5 was irradiated, but there was no enhancement of H-3.
23. The chemical shifts of the benzylidene protons of compounds 5 appeared as doublets (J=1.5-1.8 Hz) at δ 7.6-7.75 ppm, comparable to the chemical shifts of the E-isomers of some related compounds reported in the literature, see for examples: (a) Hwang, E.-I.; Yun, B.-S.; Kim, Y.-K.; Kwon, B.-M.; Kim, H.-G.; Lee, H.-B.; Jeong, W.-J.; Kim, S.-U. J. Antibiot. 2000, 53, 903-911; (b) Banerji, J.; Das, B.; Chatterjee, A.; Shoolery, J. N. Phytochemistry 1984, 23, 2323-2327; (c) Stevens, D. R.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1992, 633-637.
24. Enhancements of 9.8 and 12.2% of H-4 and H-5 of 5h were observed upon irradiation of H-5 and H-4, respectively.
25. Albright J.D. Tetrahedron. 39:1983;3207-3233. and references cited therein.
26. Reutrakul V., Nimgirawath S., Panichanun S., Ratananukul P. Chem. Lett. 1979;399-400.
27. Stetter H. Angew. Chem., Int. Ed. Engl. 15:1976;639-712.
28. Stetter H., Kuhlmann H. Org. React. 40:1991;407-438.