9570
S. Raju et al. / Tetrahedron 62 (2006) 9554–9570
6
0, 3270; (i) Larock, R. C.; Doty, M. J.; Han, X. J. Org. Chem.
Fairlamb, I. J. S.; Lee, A. F.; Loe-Mie, F.; Niemel €a , E. H.;
O’Brien, C. T.; Whitwood, A. C. Tetrahedron 2005, 61,
9827; (h) Collings, J. C.; Parsons, A. C.; Porr ꢀe s, L.; Beeby,
A.; Batsanov, A. S.; Howard, J. A. K.; Lydon, D. P.; Low,
P. J.; Fairlamb, I. J. S.; Marder, T. B. Chem. Commun. 2005,
2666; (i) Niemel €a , E. H.; Lee, A. F.; Fairlamb, I. J. S.
Tetrahedron Lett. 2004, 45, 3593; (j) Fairlamb, I. J. S.; Lu,
F.-J.; Schmidt, J.-P. Synthesis 2003, 2564; (k) Marrison,
L. R.; Dickinson, J. M.; Fairlamb, I. J. S. Bioorg. Med.
Chem. Lett. 2002, 12, 3509.
1999, 64, 8770; (j) Rossi, R.; Bellina, F.; Biagetti, M.;
Catanese, A.; Mannina, L. Tetrahedron Lett. 2000, 41, 5281.
. (a) Campaigne, E. Comprehensive Heterocyclic Chemistry;
Katritzky, A. R., Ed.; Pergamon: New York, NY, 1984; Vol.
3
4, pp 911–913; (b) Burger, A. Prog. Drug Res. 1991, 37, 287;
(
c) Colotta, V.; Catarzi, D.; Varano, F.; Melani, F.;
Filacchioni, G.; Cecchi, L.; Trincavelli, L.; Martini, C.;
Lucacchini, A. Il Farmaco 1998, 53, 189; (d) Catarzi, D.;
Cecchi, L.; Colotta, V.; Filacchioni, G.; Martini, C.; Tacchi,
P.; Lucacchini, A. J. Med. Chem. 1995, 38, 1330; (e) For exam-
ple, thiophene isosteres of the potassium channel opener cro-
makalim were found to be 10-fold more potent than
cromakalim when tested for oral antihypertensive activity in
spontaneously hypertensive rats, see: Sanfilippo, P. J.;
McNally, J. J.; Press, J. B.; Fitzpatrick, L. J.; Urbanski, M. J.;
Katz, L. B.; Giardino, E.; Falotico, R.; Salata, J.; Moore,
J. B., Jr.; Miller, W. J. Med. Chem. 1992, 35, 4425; (f) For syn-
thesis and analgesic activity of pyrano[2,3-c]pyrazoles, see:
Ueda, T.; Mase, H.; Oda, N.; Ito, I. Chem. Pharm. Bull. 1981,
9. (a) Tietze, L. F. Chem. Rev. 1996, 96, 115; (b) Lira, R.; Wolfe,
J. P. J. Am. Chem. Soc. 2004, 126, 13906; (c) Loones, K. T. J.;
Maes, B. U. W.; Dommisse, R. A.; Lemiere, G. L. F. Chem.
Commun. 2004, 2466; (d) Zhu, G.; Zhang, Z. Org. Lett. 2004,
6, 4041; (e) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.;
Stecker, F. Angew. Chem., Int. Ed. 2004, 44, 257; (f) Wasilke,
J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev.
2005, 105, 1001; (g) Pal, M.; Dakarapu, R.; Parasuraman, K.;
Subramanian, V.; Yeleswarapu, K. R. J. Org. Chem. 2005, 70,
7179.
1
2, 3522; (g) For example, thiophenes can undergo Diels–
10. For our earlier studies on Sonogashira-type reactions, see: (a)
Pal, M.; Parasuraman, K.; Gupta, S.; Yeleswarapu, K. R.
Synlett 2002, 1976; (b) Pal, M.; Subramanian, V.;
Parasuraman, K.; Yeleswarapu, K. R. Tetrahedron 2003, 59,
9563; (c) Pal, M.; Subramanian, V.; Yeleswarapu, K. R.
Tetrahedron Lett. 2003, 44, 8221; (d) Pal, M.; Subramanian,
V.; Batchu, V. R.; Dager, I. Synlett 2004, 1965; (e) Batchu,
V. R.; Subramanian, V.; Parasuraman, K.; Swamy, N. K.;
Kumar, S.; Pal, M. Tetrahedron 2005, 41, 9869.
11. For the synthesis of 3-iodo-thiophene-2-carboxylic acid (1),
see: Duffault, J.-M.; Tellier, F. Synth. Commun. 1998, 28, 2467.
12. Crystallographic data (excluding structure factors) for 3a have
been deposited with the Cambridge Crystallographic Data
Centre as supplementary publication numbers CCDC 607010.
13. Glover, B.; Harvey, K. A.; Liu, B.; Sharp, M. J. Org. Lett. 2003,
5, 301.
14. (a) Coupling of 3-iodothiophenes with terminal alkynes under
Sonogashira conditions are common in the literature, see for
example: Ye, X.-S.; Wong, H. N. C. J. Org. Chem. 1997, 62,
1940; (b) Padwa, A.; Chiacchio, U.; Fairfax, D. J.; Kassir,
J. J.; Litrico, A.; Semones, M. A.; Xu, S. L. J. Org. Chem.
1993, 58, 6429.
15. Conversion of Pd(0) to Pd(II) species under Sonogashira con-
dition has been proposed by Lu et al., see: Lu, X.; Huang,
X.; Ma, S. Tetrahedron Lett. 1993, 34, 5963; This Pd(II) species
was thought to be responsible for the cyclization of ynenoic
acid via the s-vinyl-palladium intermediate, see also:
Yanagihara, N.; Lambert, C.; Iritani, K.; Utimoto, K.;
Nozaki, H. J. Am. Chem. Soc. 1986, 108, 2753.
Alder reactions through their 1,1-dioxide derivatives, see:
Press, J. B.; Russell, R. K. Progress in Heterocyclic
Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon:
Oxford, 1992; Vol. 4, pp 62–80; (h) Ram, V. J.; Goel, A.;
Shukla, P. K.; Kapil, A. Bioorg. Med. Chem. Lett. 1997, 7,
3101.
4
. For synthesis of related derivatives, see: (a) Mladenovic, S. A.;
Castro, C. E. J. Heterocycl. Chem. 1968, 5, 227; (b) Mentzer, B.
Bull. Soc. Chim. Fr. 1945, 12, 292; (c) Zhang, Y.; Herndon,
J. W. J. Org. Chem. 2002, 67, 4177; For other examples of
the thienopyrone ring system, see: (d) Jackson, P. M.; Moody,
C. J.; Shah, P. J. Chem. Soc., Perkin Trans. 1 1990, 2909; (e)
Jackson, P. M.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1
1990, 681.
5
. (a) Subramanian, V.; Batchu, V. R.; Barange, D.; Pal, M. J. Org.
Chem. 2005, 70, 4778; (b) A preliminary report on part of this
work has appeared, see: Raju, S.; Batchu, V. R.; Swamy, N. K.;
Dev, R. V.; Babu, J. M.; Kumar, P. R.; Mukkanti, K.; Pal, M.
Tetrahedron Lett. 2006, 47, 83.
. For leading references, see: (a) Sashida, H.; Kawamukai.
Synthesis 1999, 1145; (b) Yao, T.; Larock, R. C. J. Org.
Chem. 2003, 68, 5936; (c) Biagetti, M.; Bellina, F.; Carpita,
A.; Stabile, P.; Rossi, R. Tetrahedron 2002, 58, 5023; (d)
Rossi, R.; Carpita, A.; Bellina, F.; Stabile, P.; Mannina, L.
Tetrahedron 2003, 59, 2067; (e) Peng, A.-Y.; Ding, Y.-X.
Org. Lett. 2004, 6, 1119.
6
7
8
. (a) Liao, H.-Y.; Cheng, C.-H. J. Org. Chem. 1995, 60, 3711; (b)
Kundu, N. G.; Pal, M.; Nandi, B. J. Chem. Soc., Perkin Trans. 1
1998, 561; (c) Kundu, N. G.; Pal, M. J. Chem. Soc., Chem.
Commun. 1993, 86.
. See for example: (a) Wu, J.; Liao, Y.; Yang, Z. J. Org. Chem.
2001, 66, 3642; (b) Fu, X.; Zhang, S.; Yin, J.; Schumacher,
D. P. Tetrahedron Lett. 2002, 43, 6673; (c) Kabalka, G. W.;
Dong, G.; Venkataiah, B. Tetrahedron Lett. 2004, 45, 5139;
16. Trost, B. M.; Chan, C.; Ruhter, G. J. Am. Chem. Soc. 1987, 109,
3486.
17. 3-Hex-1-ynyl thiophene-2-carboxylic acid was prepared by
1
4b
Sonogashira coupling
acid methyl ester with 1-hexyne in the presence of Et N in
of 3-iodo thiophene-2-carboxylic
3
ꢀ
DMF at 60 C for 6 h followed by hydrolysis of the resulting
ester in aqueous methanol.
(
d) Catellani, M.; Chiusoli, G. P.; Fagnola, M. C.; Solari, G.
Tetrahedron Lett. 1994, 35, 5923. See also Ref. 6b; For the
synthesis of 4-alkynyl-2-pyrones, see: (e) Marrison, L. R.;
Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Tetrahedron
Lett. 2002, 43, 8853; (f) Fairlamb, I. J. S.; O’Brien, C. T.;
Lin, Z.; Lam, K. C. Org. Biomol. Chem. 2006, 4, 1213; (g)
18. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.;
Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.;
Gray-Goodrich, M.; Campbell, H.; Mayo, J.; Boyd, M. J. Natl.
Cancer Inst. 1991, 83, 757.
19. Duffault, J.-M.; Tellier, F. Synth. Commun. 1998, 28, 2467.