The Aqueous Trimethylamine Mediated Baylis-Hillman Reaction

REFERENCES AND NOTES

• Basavaiah , D. , Dharma Rao , P. and Suguna Hyma , R. 1996 . Tetrahedron , 52 : 8001
   Web of Science ®Google Scholar
• Ciganek , E. 1997 . Organic Reactions , Edited by: Paquette , L. A. vol. 51 , 201 – 350 . New York : John Wiley & Sons .
   Google Scholar
• Drewes , S. E. and Roos , G. H.P. 1988 . Tetrahedron , 44 : 4653
   Web of Science ®Google Scholar
• Basavaiah , D. , Bakthadoss , M. and Pandiaraju , S. 1998 . Chem. Commun. , : 1639
   Web of Science ®Google Scholar
• Basavaiah , D. , Krishnamacharyulu , M. , Suguna Hyma , R. and Pandiaraju , S. 1997 . Tetrahedron Lett. , 38 : 2141
   Web of Science ®Google Scholar
• Basavaiah , D. , Krishnamacharyulu , M. , Suguna Hyma , R. , Sarma , P. K.S. and Kumaragurubaran , N. 1999 . J. Org. Chem. , 64 : 1197
   Web of Science ®Google Scholar
• Basavaiah , D. , Sarma , P. K.S. and Bhavani , A. K.D. 1994 . J. Chem. Soc., Chem. Commun. , : 1091
   Google Scholar
• Rezgui , F. and El Gaied , M. M. 1998 . Tetrahedron Lett. , 39 : 5965
   Web of Science ®Google Scholar
• Kataoka , T. , Iwama , T. and Tsujiyama , S. 1998 . Chem. Commun. , : 197
   Web of Science ®Google Scholar
• Barrett , A. G.M. , Cook , A. S. and Kamimura , A. 1998 . Chem. Commun. , : 2533
   Web of Science ®Google Scholar
• Hayase , T. , Shibata , T. , Soai , K. and Wakatsuki , Y. 1998 . Chem. Commun. , : 1271
   Web of Science ®Google Scholar
• Nakagawa , K. , Makino , M. and Kita , Y. Eur. Patent Appl. EP . 669,312 . 1995 .
   Google Scholar
• 1995 . Chem. Abstr. , 123 : 285218v
   Google Scholar
• Bode , M. L. and Kaye , P. T. 1993 . J. Chem. Soc., Perkin Trans. , 1 : 1809 This molecule is known in the literature and was prepared via the DABCO catalyzed coupling of 2-pyridinecarboxaldehyde with methyl acrylate in CHCl3 for 3 days in 94% yield. See
   Google Scholar
• Preparation of molecule 1 (Representative procedure): A mixture of pyridine-2-carboxaldehyde (10 mmol, 1.071 g), methyl acrylate (30 mmol, 2.583 g) and aqueous trimethylamine (30% w/v) (12 mmol, 2.36 mL) was heated at 60°C for 4 hours. The reaction mixture was then cooled to room temperature, layers separated and the aqueous layer was extracted with ether (3 × 10 mL). The combined organic layer was dried over anhydrous sodium sulfate, concentrated and silica gel column chromatography (5% ethyl acetate in hexanes) of the crude product thus obtained, has provided 1.196 g (62%) of methyl 3-hydroxy-2-methylene-3-(pyrid-2-yl)propanoate (1) as a colorless oil.
   Google Scholar
• Masuyama , Y. , Nimura , Y. and Kurusu , Y. 1991 . Tetrahedron Lett. , 32 : 225
   Web of Science ®Google Scholar
• Drewes , S. E. , Loizou , G. and Roos , G. H.P. 1987 . Synth. Commun. , 17 : 291
   Web of Science ®Google Scholar
• Preparation of molecule 14: A mixture of cyclohex-2-en-1-one (20 mmol, 1.923 g) and aqueous trimethylamine (30% w/v) (24 mmol, 4.72 mL) was heated at 60°C for 6 hours. Usual work up followed by silica gel column chromatography (10% ethyl acetate in hexanes) has provided 0.680 g (35%) of 14 as pale yellow oil.
   Google Scholar
• Foucaud , A. and El Guemmout , F. 1989 . Bull. Soc. Chim. Fr. , : 403 These molecules are known, and their spectral data (IR, 1H and/or 13C NMR) are reported in the literature. Spectral data of these molecules are agreement with the literature data. For molecule 1, see
   Google Scholar
• Fort , Y. , Berthe , M. C. and Caubere , P. 1992 . Tetrahedron , 48 : 6371 For molecule 2, see: ref: 8. For molecule 4, see: ref: 15. For molecules 7 and 9, see
   Web of Science ®Google Scholar
• Novarro , C. , Castaing , D-M. , Colombani , D. and Maillard , B. 1993 . Synth. Commun. , 23 : 1025 For molecule 10, see: ref: 10b. For molecule 11, see: ref: 16. For molecule 13, see
   Web of Science ®Google Scholar
• Mubarak , M. S. , Pagel , M. , Marcus , L. M. and Peters , D. G. 1998 . J. Org. Chem. , 63 : 1319 For molecule 14, see
   Web of Science ®Google Scholar
• Elemental analysis of selected products: Elemental analysis is furnished for either unknown molecules or the known molecules whose spectral data is not fully reported in the literature., Recorded on a Perkin-Elmer 240C-CHN analyzer.
   Google Scholar
• Compound 4: m.p.: 72-73°C (lit.15 74°C); Compound 10: b.p.: 71-72°C/2mm; Compound 11: b.p.: 78-80°C/2mm (lit.16 65-70°C/1mm); Compound 12: b.p.: 80°C/0.5mm; Compound 13: b.p.: 76°C/0.5mm.
   Google Scholar
• Foucaud , A. and Rouille , E. 1990 . Synthesis , : 787
   Web of Science ®Google Scholar
• Villieras , J. and Rambaud , M. 1982 . Synthesis , 11 : 924
   Web of Science ®Google Scholar