Synthesis of Functionalized Hydroxyphthalides and Their Conversion to 3-Cyano-1(3H)-isobenzofuranones. The Diels-Alder Reaction of Methyl 4,4-Diethoxybutynoate and Cyclohexadienes

Journal of Organic Chemistry

Volumn 50, Issue 6, 1985, Pages 805-810

  Freskos, John N ^a   Morrow, Gary W ^a   Swenton, John S ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000346689     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00206a016     Document Type: Article

References (16)

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4. Freskos, J. N.; Morrow, G. W.; Sercel, A. D.; Swenton, J. S. Tetrahedron, “Symposium in Print” 1984, 40, 4625. (b) For a preliminary report on the Diels-Alder route to hydroxypthalides, see: Freskos, J.; Cynkowski, T.; Swenton, J. J. Chem. Soc., Chem. Commun. 1984, 819.
5. Thomson, R. H. “Naturally Occurring Quinones” Academic Press: New York, 1971; Chapter 6.
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7. Reduction of phthalic and other cyclic anhydrides with a variety of reducing agents usually affords the corresponding phthalides: (a) Bailey, D. M.; Johnson, R. E. J. Org. Chem. 1970, 35, 3574. (b) Mellows, S. M.; Sammes, P. G. J. Chem. Soc. D 1971, 21. (c) Birch, A. J.; Russell, R. A. Aust. J. Chem. 1971 24, 1975. (d) Burke, D. E.; LeQuesne, P. W. J. Org. Chem. 1971, 36, 2397. (e) Shroff, C. C.; Stewart, W. S.; Uhm, S. J.; Wheeler, J. W. J. Org. Chem. 1971; 36, 3356. (f) Koizumi, T.; Yamamoto, N.; Yoshii, E. Chem. Pharm. Bull. 1973, 21, 312. (g) Subba Rao, B. C. Curr. Sci. 1961, 30, 218. (h) McAlles, A. J.; McCrindle, R.; Sneddon, D. W. J. Chem. Soc., Perkin Trans. 1 1977, 2030, 2037. (9) DeSilva, S. O.; Reed, J. N.; Snieckus, V. Tetrahedron Lett. 1978, 5099. (b) Beak. P.; Brown, R. A. J. Org. Chem. 1979, 44, 4463. (c) Plauman, H. P.; Keay, B. A.; Rodrigo, R. Tetrahedron Lett. 1979, 4921. (d) Zielger, F. E.; Fowler, K. W. J. Org. Chem. 1976, 41, 1564. (e) Commins, D. L.; Brown, J. D.; Mantlo, N. B. Tetrahedron Lett. 1982, 23, 3979. (f) Sinhababu, A. K.; Borchardt, R. T. J. Org. Chem. 1983, 48, 2356. (g) Prabhu, U.; Eapen, K. C.; Tamborski, C. J. Org. Chem. 1984, 49, 2792.
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10. Harland, P. A.; Hodge, P. Synthesis 1982, 223; 1983, 419. We regret having not referenced these key papers in our preliminary note on the Diels-Alder chemistry reported herein and wish to thank Professor Hodge for informing us of his work.
11. The 1,3-dipolar cycloadditions of 12 have been studied. (a) Farina, F.; Martin, M. V.; Sanchez, F. An. Quim. 1982, 78C, 332. (b) Farina, F.; Fernadez, P.; Martin, M. K.; Martin, M. V.; Sanchez, F. An. Quim. 1983, 79C, 333, (c) See also: Gorgues, A.; Simon, A.; LeCoq, A.; Corre, F. Tetrahedron Lett. 1981, 22, 625. (d) Professor F. Farina has informed us that he has studied the Diels-Alder reaction of 12 with simple dienes.
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13. The conversion of 1-methoxycyclohexa-l,4-dienes to the conjugated isomer under Diels-Alder conditions has been studied and proposed to occur via a charge-transfer complex. Birch, A. J.; Dastur, K. P. Tetrahedron Lett. 1972, 4195; J. Chem. Soc., Perkin Trans. 1 1973, 1650.
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15. 2d has recently reported this method to be unreliable.
16. Marumo, S.; Sasaki, K.; Ohkuma, K.; Ansai, K.; Suzuki, S. Agric. Biol. Chem. 1968, 209. (23) (a) Gannon, W.; House, H. O. Org. Synth. 1960, 40, 41. (b) No attempt was made to obtain the pure silyl enol ether since the Diels-Alder reaction and subsequent distillation gave a pure product in excellent overall yield.