One-pot synthesis of chromenylfurandicarboxylates and cyclopenta[b] chromenedicarboxylates involving zwitterionic intermediates. A DFT investigation on the regioselectivity of the reaction

Journal of Organic Chemistry

Volumn 75, Issue 6, 2010, Pages 1948-1955

  Terzidis, Michael A ^a   Stephanidou Stephanatou, Julia ^a   Tsoleridis, Constantinos A ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

BASIS SETS; CHEMICAL EQUATIONS; CHROMONES; DFT CALCULATION; ESTER GROUPS; IN-SITU; INTERMEDIATE PRODUCT; MECHANISTIC SCHEME; NMR CHEMICAL SHIFTS; ONE-POT SYNTHESIS; TRANSITION STRUCTURES; ZWITTERIONIC INTERMEDIATE;

ACETYLENE; ESTERS; LIGHTING; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROBABILITY DENSITY FUNCTION; REGIOSELECTIVITY; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

REACTION INTERMEDIATES;

3 FORMYLCHROMONE DERIVATIVE; ACETYLENEDICARBOXYLATE DERIVATIVE; AMPHOLYTE; CARBOXYLIC ACID DERIVATIVE; CHROMENYLFURADICARBOXYLATE DERIVATIVE; CHROMENYLFURANDICARBOXYLATE DERIVATIVE; CHROMONE DERIVATIVE; CYANIDE; CYCLOHEXYL ISOCYANIDE; CYCLOPENTA[B]CHROMENEDICARBOXYLATE DERIVATIVE; DIMETHYL 2 (TERT BUTYLAMINO) 5 (4 OXO 4H CHROMEN 3 YL)FURAN 3,4 DICARBOXYLATE; TERT BUTYL ISOCYANIDE TECHNETIUM TC 99M; TETRAMETHYL 10 (TERT BUTYLAMINO) 11 OXO 7,11 DIHYDROCYCLOHEPTA[B]CHROMENE 6,7,8,9 TETRACARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

BENZOPYRANS; CARBOXYLIC ACIDS; CYCLOPENTANES; FURANS; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM;

EID: 77949821631     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902702j     Document Type: Article

References (66)

1. (a) Dewick, P. M. The Flavonoids: Advances in Research Since 1986; Harbome, J. B., Ed.; Chapman & Hall: New York, 1994; p 117.
2. (b) Gill, M. The Chemistry of Natural Products, 2nd ed.; Thomson, R. H., Ed.; Blackie: Surrey, U.K., 1993; p 60.
3. (c) Flavonoids in the Living Systems: Advances in Experimental Medicine and Biology; Manthey, J. A., Buslig, B. S., Eds.; Plenum: New York, 1998; Vol.439.
4. (a) Korkina, G. L.; Afanas'ev, I. B. Advances in Pharmacology; Sies, H., Ed.; Academic Press: San Diego, 1997; Vol.38, p 151.
5. (b) Comprehensive Medicinal Chemistry; Hansen, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon: New York, 1990; Vol.6.
6. (a) Hsung, R. P. J. Org. Chem. 1997, 62, 7904.
7. (b) Valenti, P.; Bisi, A.; Rampa, A.; Belluti, F.; Gobbi, S.; Zampiron, A.; Carrara, M. Bioorg. Med. Chem. 2000, 8, 239.
8. (a) Larget, R.; Lockhart, B.; Renard, P.; Largeron, M. Bioorg. Med. Chem. Lett. 2000, 10, 835.
9. (b) Groweiss, A.; Cardellina, J. H.; Boyd, M. R. J. Nat. Prod. 2000, 63, 1537.
10. (c) Pietta, P. G. J. Nat. Prod. 2000, 63, 1035.
11. (d) Donner, C. D.; Gill, M.; Tewierik, M. Molecules 2004, 9, 498.
12. Ghosh, C. K. J. Hetercycl. Chem. 1983, 20, 1437.
13. Sabitha, G. Aldrichimica Acta 1996, 29, 15.
14. Ghosh, C. K.; Ghosh, C. Indian J. Chem.. 1997, 36B, 968.
15. (a) Ghosh, C. K. Heterocycles 2004, 63, 2875.
16. (b) Ghosh, C. K.; Patra, A. J. Heterocycl. Chem. 2008, 45, 1529.
17. (a) Cremins, P. J.; Saengchantara, S. T.; Wallace, T. W. Tetrahedron 1987, 43, 3075.
18. (b) Sandulache, A; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105.
19. Eiden, F.; Breugst, J. Chem. Ber. 1979, 112, 1791.
20. (a) Quiroga, J.; Mejía, D.; Insuasty, B.; Abonía, R.; Nogueras, M.; Sánchez, A.; Cobo, J.; Low, J. N. J. Heterocycl Chem. 2002, 39, 51.
21. (b) Quiroga, J.; Rengifo, A.; Insuasty, B.; Abonía, R.; Nogueras, M.; Sánchez, A. Tetrahedron Lett. 2002, 43, 9061.
22. (c) Vanden Eynde, J. J.; Hecq, N.; Kataeva, O.; Kappe, C. O. Tetrahedron 2001, 57, 1785.
23. (a) Sabitha, G.; Babu, R. S.; Yadav, J. S. Synth. Commun. 1998, 28, 4571.
24. (b) Bandyopadhyay, C.; Sur, K. R.; Patra, R.; Sen, A. Tetrahedron 2000, 56, 3583.
25. (a) Singh, G.; Singh, L.; Ishar, M. P. S. Tetrahedron 2002, 58, 7883.
26. (b) Risitano, F.; Grossi, G.; Foti, F. J. Heterocycl. Chem. 2001, 38, 1083.
27. (c) Bruno, O.; Schenone, S.; Ranise, A.; Bondavalli, F.; Barocelli, E.; Ballabeni, V.; Chiavarini, M.; Bertoni, S.; Tognolini, M.; Impicciatore, M. Bioorg. Med. Chem. 2001, 9, 629.
28. (a) Tietze, L. F. Chem. Rey. 1996, 96, 115.
29. (b) Posner, G. H. Chem. Rev. 1986, 86, 831.
30. (c) Ramón, D. J.; Yus, M. Angew. Chem. Int. Ed. 2005, 44, 1602.
31. (a) Dömling, A.; Ugi, I. Angew. Chem.. Int. Ed. 2000, 39, 3168.
32. (b) Domlmg, A. Chem. Rev. 2006, 106, 17.
33. (c) Akritopoulou-Zanze, I. Curr. Opin. Chem. Biol. 2008, 12, 324.
34. (d) El Kaim, L.; Grimaud, L. Tetrahedron 2009, 65, 2153.
35. (a) Terzidis, M.; Tsoleridis, C. A.; Stephanidou-Stephanatou, J. Tetrahedron Lett. 2005, 46, 7239.
36. (b) Terzidis, M.; Tsoleridis, C. A.; Stephanidou-Stephanatou J. Tetrahedron 2007, 63, 7828-12009
37. (c) Terzidis, M. A.; Tsoleridis, C. A.; Stephanidou-Stephanatou, J. Synlett 2009, 229.
38. (d) Terzidis, M. A.; Tsoleridis, C. A.; Stephanidou-Stephanatou, J. Tetrahedron Lett. 2009, 50, 1196.
39. (e) Terzidis, M. A.; Dimitriadou, E.; Tsoleridis, C. A.; StephanidouStephanatou, J. Tetrahedron Lett. 2009, 50, 2174.
40. Frisch, M. J.; Tracks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Buran t, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Peterson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, Y. C.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Rev. B.02; Gaussian: Pittsburgh, PA, 2003.
41. (a) Halgren, T. A.; Lipscomp, W. N. Chem. Phys. Lett. 1977, 49, 225.
42. (b) Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49.
43. (c) Peng, C.; Schlegel, H. B. Isr. J. Chem. 1994, 33, 449.
44. (a) Cancès, M. T.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032.
45. (b) Cossi, M.; Barone, V.; Mennucci, B.; Tomasi, J. Chem. Phys. Lett. 1998, 286, 253.
46. (c) Mennucci, B.; Tomasi, J. J. Chem. Phys. 1996, 106, 5151.
47. Raj, T.; Ishar, M. P. S.; Gupta, V.; Pannu, A. P. S.; Kanwal, P.; Singh, G. Tetrahedron Lett. 2008, 49, 243.
48. (a) Plaskon, A. S.; Ryabukhin, S. V.; Volochnyuk, D. M.; Gavrilenko, K. S.; Shivanyuk, A. N.; Tolmachev, A. A. J. Org. Chem. 2008, 73, 6010.
49. (b) Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2007, 3155.
50. (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019.
51. (b) Nair, V.; Vinod, A. U.; Abhilash, N.; Menon, R. S.; Santhi, V.; Varma, R. L.; Viji, S.; Mathew, S.; Srinivas, R. Tetrahedron 2003, 59, 10279.
52. (c) Yadav, J. S.; Reddy, B. V. Subba; Shubashree, S.; Sadashiv, K.; Naidu, Jaisree J. Synthesis 2004, 2376.
53. (d) Azizian, J.; Mohammadizadeh, M. R.; Mohammadi, A. A.; Karimi, A. R. Heteroat Chem. 2005, 16, 259.
54. (e) Adib, M.; Sayahi, M. H.; Koloogani, S. A.; Mirzaei. P. Hely. Chim. Acta 2006, 89, 299.
55. (f) Asghari, S.; Qandalee, M. Acta Chim. Slov. 2007, 54, 638.
56. (g) Hazeri, N.; Maghsoodlou, M. T.; Habibi-Khorassani, S. M.; Marandi, G.; Khandan-Barani, K.; Ziyaadini, M.; Aminkhani, A. Arkivoc 2007, i, 173.
57. (a) Zhao, L.; Brinton, R. D. J. Med. Chem. 2005, 48, 3463.
58. (b) Edwards, B. S.; Bologa, C.; Young, S. M.; Balakin, K. V.; Prossnitz, E. R.; Savchuck, N. P.; Sklar, L. A.; Oprea, T. I. Mol. Pharmacol. 2005, 68, 1301.
59. (c) Sayed, H. M.; Mohamed, M. H.; Farag, S. F.; Mohamed, G. A.; Proksch, P. Nat. Prod. Res. 2007, 21, 343.
60. (a) Wang, H.-J.; Gloer, J. B.; Scott, J. A.; Malloch, D. Tetrahedron Lett. 1995, 36, 5847.
61. (b) Fujimoto, H.; Inagaki, M.; Satoh, Y.; Yoshida, E.; Yamazaki, M. Chem. Pharm. Bull. 1996, 44, 1090.
62. (c) Lin, L.-J.; Topcu, G.; Lotter, H.; Ruangrungsi, N.; Wagner, H.; Pezzuto, J. M.; Cordell, G. A. Phytochemistry 1992, 31, 4333.
63. (d) Ondeyka, J. G.; Zink, D.; Basilio, A.; Vicente, F.; Bills, G.; Diez, M. T.; Motyl, M.; Dezeny, G.; Byrne, K.; Singh, S. B. J. Nat. Prod. 2007, 70, 668.
64. (a) Mori, K.; Audran, G.; Monti, H. Synlett 1998, 259.
65. (b) Thasana, N.; Ruchirawat, S. Tetrahedron Lett. 2002, 43, 4515.
66. Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023.