Efficient synthesis of 3-carboxylate pyrroles using microwave irradiation

Tetrahedron Letters

Volumn 46, Issue 7, 2005, Pages 1061-1062

  Grassi, Giovanni ^a   Foti, Francesco ^a   Risitano, Francesco ^a   Zona, Domenico ^a  

^a UNIVERSITY OF MESSINA   (Italy)

Author keywords

Dipolar cycloaddition; Mesoionic compounds; Microwave synthesis; Regioselectivity

Indexed keywords

1,3 OXAZOLIUM 5 OXIDE; ESTER DERIVATIVE; OXIDE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; MICROWAVE IRRADIATION; QUANTUM YIELD; STEREOCHEMISTRY;

EID: 12344284050     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.102     Document Type: Article

References (13)

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3. A. Padwa W.H. Pearson Synthetic Applications of Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Product 2002 John Wiley & Sons New York 681 754
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8. General procedure: a mixture of olefin 2 (3 mmol), N-methyl-N-benzoyl- alanine (621.6 mg, 3 mmol) and acetic anhydride (1 mL) in dioxane (40 mL) was irradiated for 10 min in an open glass vial in a CEM microwave synthesiser at 100°C. After cooling the reaction to room temperature, the solvent was removed under vacuum and the residue was purified by silica gel flash column chromatography using chloroform to give the regioisomer mixture as a yellow solid or oil. Recrystallisation from 80% petroleum ether/methanol afforded 3 and 4 as colourless crystals or a pale yellow oil
9. R. Huisgen, H. Gotthard, and H.O. Bayer Angew. Chem., Int. Ed. 3 1964 135 137
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11. 2: C, 75.25; H, 7.80; N, 5.16. Found: C, 75.59; H, 7.72; N, 5.28
12. In this case, the two regioisomers 3b and 4b were obtained by the quoted means (Ref. 3) with respective yields of 13% and 16%
13. 3: C, 71.56; H, 6.71; N, 4.91. Found: C, 71.68; H, 6.75; N, 5.06