Expeditious syntheses of 3,4-dihydroisocoumarins and phthalides via a Heck-Matsuda reaction.

Expeditious syntheses of 3,4-dihydroisocoumarins and phthalides via a Heck-Matsuda reaction.

Forni, J.A.; Biajoli, A.F.P.; da Penha, E.T.; Correia, C.R.D.

Abstract:

The 3-aryl-3,4-dihydroisocoumarins and phthalides are families of natural products that exhibit an extensive list of biological activities. For example, the sweetener phyllodulcin is more effective than sucrose1a, and isoochracinic acid, is a phthalide that causes the black spot disease on Japanese pears1b. Employing Heck-Matsuda (HM) conditions, we developed an efficient protocol for the synthesis of these cores structures using arenediazonium salt 3.

The 3-aryl-3,4-dihydroisocoumarins and phthalides are families of natural products that exhibit an extensive list of biological activities. For example, the sweetener phyllodulcin is more effective than sucrose1a, and isoochracinic acid, is a phthalide that causes the black spot disease on Japanese pears1b. Employing Heck-Matsuda (HM) conditions, we developed an efficient protocol for the synthesis of these cores structures using arenediazonium salt 3.

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DOI: 10.5151/chempro-14bmos-R0044-1

Referências bibliográficas

• [1] 1.(a) Dick, W.E.; Hodge, J.E. J. Agric.Food Chem. 1978, 26, 723- 725. (b) Kameda,K.; Namika, M. Chem. Lett. 1974, 1491.
• [2] 2.(a) Heck, R.F.; Nolley, J.P J. Org. Chem. 1972, 37, 2320. (b) Kikukawa, K.; Matsuda, T. Chem. Lett. 1977, 159-162
• [3] 3. Moro, A. V.; Cardoso, F. S. P., et al. Tetrahedron Lett. 2008, 49, 5668-5671.

Como citar:

Forni, J.A.; Biajoli, A.F.P.; da Penha, E.T.; Correia, C.R.D.; "Expeditious syntheses of 3,4-dihydroisocoumarins and phthalides via a Heck-Matsuda reaction.", p-44-44. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0044-1