Benzyne-oxazole cycloadducts: isolation and retro-Diels-Alder reactions

SE Whitney, M Winters, B Rickborn

Index: Whitney, Scott E.; Winters, Michael; Rickborn, Bruce Journal of Organic Chemistry, 1990 , vol. 55, # 3 p. 929 - 935

Full Text: HTML

Citation Number: 53

Abstract

A literature procedure for generating benzyne from 1-aminobenzotriazole and lead tetraacetate was modified by the use of two syringe pumps to effect simultaneous addition through opposing ports of a three-neck flask. Applied to the reaction of benzyne with 4- phenyloxazole at 0" C, this modification resulted in essentially quantitative formation of cycloadduct. Retro-Dieh-Alder expulsion of benzonitrile with concurrent formation of ...

~37%

~50%

~56%

~0%

Detail

~10%

Photochemistry of 4??and 5??phenyl substituted isoxazoles

[Pavlik, James W.; St. Martin, Heather; Lambert, Karen A.; Lowell, Jennifer A.; Tsefrikas, Vikki M.; Eddins, Cheryl K.; Kebede, Naod Journal of Heterocyclic Chemistry, 2005 , vol. 42, # 2 p. 273 - 281]

Discovery of a novel class of selective non-peptide antagoni...

[Giardina, Giuseppe A. M.; Sarau, Henry M.; Farina, Carlo; Medhurst, Andrew D.; Grugni, Mario; Raveglia, Luca F.; Schmidt, Dulcie B.; Rigolio, Roberto; Luttmann, Mark; Vecchietti, Vittorio; Hay, Douglas W. P. Journal of Medicinal Chemistry, 1997 , vol. 40, # 12 p. 1794 - 1807]

Isolation of a 1: 1 oxazole-benzyne cycloadduct. An improved...

[Journal of Organic Chemistry, , vol. 53, # 23 p. 5595 - 5596]

Synthesis and biological activity of new potential agonists ...

[Chemische Berichte, , vol. 87, p. 700,706]

Facile structural elucidation of imidazoles and oxazoles bas...

[Tetrahedron, , vol. 66, # 7 p. 1465 - 1471]