Development of a Mild and Versatile Directed Cycloaddition Approach to Pyridines

作者: Sylvestre P. J. T. Bachollet , Jérôme F. Vivat , Dean C. Cocker , Harry Adams , Joseph P. A. Harrity

DOI: 10.1002/CHEM.201403916

关键词:

摘要: The aza-Diels–Alder cycloaddition of 1,2,4-triazines with alkynes offers a rapid and convenient method for the synthesis highly substituted pyridines, but often requires harsh conditions long reaction times. present study solution to these limitations by use temporary tether established Lewis acid–base complexation in situ generated alkynylboranes triazines bearing basic donor. reactions take place within 20 min at 40 °C provide direct access broad range pyridines complete predictable regiocontrol. carbon[BOND]boron bond can be further functionalised cross-coupling allowing functionality introduced after cycloaddition.

参考文章(20)
Gerhard Hilt, Konstantin I. Smolko, Alkinylboronester als effiziente Dienophile in Cobalt-katalysierten Diels-Alder-Reaktionen Angewandte Chemie. ,vol. 115, pp. 2901- 2903 ,(2003) , 10.1002/ANGE.200351404
Dale L. Boger, Diels-Alder reactions of azadienes Tetrahedron. ,vol. 39, pp. 2869- 2939 ,(1983) , 10.1016/S0040-4020(01)92154-4
E. Vedejs, R. W. Chapman, S. C. Fields, S. Lin, M. R. Schrimpf, Conversion of Arylboronic Acids into Potassium Aryltrifluoroborates: Convenient Precursors of Arylboron Difluoride Lewis Acids Journal of Organic Chemistry. ,vol. 60, pp. 3020- 3027 ,(1995) , 10.1021/JO00115A016
Jesús A. Varela, Carlos Saá, Construction of pyridine rings by metal-mediated [2 + 2 + 2] cycloaddition. Chemical Reviews. ,vol. 103, pp. 3787- 3801 ,(2003) , 10.1021/CR030677F
Damien F. Crépin, Joseph P. A. Harrity, Lewis Base Directed Cycloaddition Reactions of 2-Pyrones and Alkynylaluminum Reagents Organic Letters. ,vol. 15, pp. 4222- 4225 ,(2013) , 10.1021/OL401952K
Matthew D. Helm, Jane E. Moore, Andrew Plant, Joseph P. A. Harrity, Synthesis of Highly Substituted Pyridazines through Alkynyl Boronic Ester Cycloaddition Reactions Angewandte Chemie. ,vol. 44, pp. 3889- 3892 ,(2005) , 10.1002/ANIE.200500288
SHOETSU KONNO, SETSUYA OHBA, MATAICHI SAGI, HIROSHI YAMANAKA, Studies on as-Triazine Derivatives. IX. Synthesis of 5-Substituted 1, 2, 4-Triazine Derivatives through an Addition Reaction and Subsequent Oxidation Chemical & Pharmaceutical Bulletin. ,vol. 35, pp. 1378- 1382 ,(1987) , 10.1248/CPB.35.1378
Stéphane Diring, Pascal Retailleau, Raymond Ziessel, A Rational Protocol for the Synthesis of Arylated Bipyridine Ligands via a Cycloaddition Pathway Journal of Organic Chemistry. ,vol. 72, pp. 10181- 10193 ,(2007) , 10.1021/JO7019866
Duncan L. Browne, Jérôme F. Vivat, Andrew Plant, Enrique Gomez-Bengoa, Joseph P. A. Harrity, Investigation of the scope and regiochemistry of alkynylboronate cycloadditions with sydnones. Journal of the American Chemical Society. ,vol. 131, pp. 7762- 7769 ,(2009) , 10.1021/JA902460N