Accelerated Amination of Baylis–Hillman Acetates Under Ultrasound Irradiation

REFERENCES

• Drewes , S. E. ; Roos , G. H. P. Synthetic potential of the tertiary-amine-catalysed reaction of activated vinyl carbanions with aldehydes . Tetrahedron 1988 , 44 , 4653 – 4670 .
   Web of Science ®Google Scholar
• Basavaiah , D. ; Rao , P. D. ; Hyma , R. S. The Baylis–Hillman reaction: A novel carbon–carbon bond-forming reaction . Tetrahedron 1996 , 52 , 8001 – 8062 .
   Web of Science ®Google Scholar
• Basavaiah , D. ; Rao , A. J. ; Satyanarayana , T. Recent advances in the Baylis–Hillman reaction and applications . Chem. Rev. 2003 , 103 , 811 – 892 .
   PubMed Web of Science ®Google Scholar
• Langer , P. New strategies for the development of an asymmetric version of the Baylis–Hillman reaction . Angew. Chem. Int. Ed. 2000 , 39 , 3049 – 3052 .
   PubMed Web of Science ®Google Scholar
• Kim , J. N. ; Lee , K. Y. Synthesis of cyclic compounds from the Baylis–Hillman adducts . Curr. Org. Chem. 2002 , 6 , 627 – 645 .
   Web of Science ®Google Scholar
• Singh , V. ; Batra , S. Advances in the Baylis–Hillman reaction-assisted synthesis of cyclic frameworks . Tetrahedron 2008 , 64 , 4511 – 4574 .
   Web of Science ®Google Scholar
• Ciganek , E. In Organic Reactions ; L. A. Paquette (Ed.); John Wiley & Sons : New York , 1997 ; vol. 51 , p. 201 .
   Google Scholar
• Masson , G. ; Housseman , C. ; Zhu , J. P. The enantioselective Morita–Baylis–Hillman reaction and its aza counterpart . Angew. Chem. Int. Ed. 2007 , 46 , 4614 – 4628 .
   PubMed Web of Science ®Google Scholar
• Shi , Y. L. ; Shi , M. Aza–Baylis–Hillman reactions and their synthetic applications . Eur. J. Org. Chem. 2007 , 18 , 2905 – 2916 .
   Google Scholar
• Kim , S. C. ; Gowrisankar , S. ; Kim , J. N. Synthesis of polysubstituted quinolines from the acetates of Baylis–Hillman adducts: Aza-Claisen rearrangement as the key step . Bull. Korean Chem. Soc. 2005 , 26 , 1001 – 1004 .
   Google Scholar
• Pathak , R. ; Nag , S. ; Batra , S. A facile synthesis of 3-methylene-4-aryl-1,3,4,5-tetrahydrobenzo[ b ][1,4]diazepin-2-ones and 3-arylmethylene-4,5-dihydro-3 H -benzo[ b ][1,4]diazepin-2-ylamines . Synthesis 2006 , 4205 – 4211 .
   Google Scholar
• Lee , C. G. ; Lee , K. Y. ; Lee , S. ; Kim , J. N. Chemical transformation of Baylis–Hillman adducts: The reaction of methyl 3-arylamino-2-methylene-3-phenylpropanoates in polyphosphoric acid . Tetrahedron 2005 , 61 , 1493 – 1499 .
   Google Scholar
• Pathak , T. R. ; Madapa , S. ; Batra , S. Trifluoroacetic acid: A more effective and efficient reagent for the synthesis of 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones and 3-arylmethyl-2-amino-quinolines from Baylis–Hillman derivatives via Claisen rearrangement. Tetrahedron 2007, 63, 451–460.
   Web of Science ®Google Scholar
• Gowrisankar , S. ; Lee , H. S. ; Kim , J. M. ; Kim , J. N. Pd-mediated synthesis of 2-arylquinolines and tetrahydropyridines from modified Baylis–Hillman adducts . Tetrahedron Lett. 2008 , 49 , 1670 – 1673 .
   Google Scholar
• Jadidi , K. ; Gharemanzadeh , R. ; Mehrdad , M. ; Darabi , H. R. ; Khavasi , H. R. ; Asgari , D. A facile synthesis of novel pyrrolizidines under classical and ultrasonic conditions . Ultrason. Sonochem. 2008 , 15 , 124 – 128 .
   PubMed Web of Science ®Google Scholar
• Ramesh , E. ; Raghanatham , R. A facile synthesis of chromeno[4,3-b]pyrroles derived from allyl derivatives of Baylis–Hillman adducts through intramolecular 1,3-dipolar cycloaddition using ultrasonication . Tetrahedron Lett. 2008 , 49 , 1125 – 1128 .
   Google Scholar
• Kumar , V. ; Sharma , A. ; Sharma , M. ; Sharma , U. K. ; Sinha , A. K. DDQ-catalyzed benzylic acetoxylation of arylalkanes: A case of exquisitely controlled oxidation under sonochemical activation . Tetrahedron 2007 , 63 , 9718 – 9723 .
   Google Scholar
• Fu , N. ; Zhang , Y. R. ; Yang , D. ; Chen , B. H. ; Wu , X. L. A rapid synthesis of 1-ferrocenyl-2-arylacetylenes under ultrasound irradiation . Catal. Commun. 2008 , 9 , 976 – 979 .
   Google Scholar
• Dandia , A. ; Gautam , S. ; Jain , A. K. An efficient synthesis of fluorine-containing substituted spiro[piperidine-4,4′-pyrano[3,2-c]quinoline]-3′-carbonitrile by nonconventional methods . J. Fluorine. Chem. 2007 , 128 , 1454 – 1460 .
   Web of Science ®Google Scholar
• Xia , M. ; Lu , Y. D. Ultrasound-assisted one-pot approach to β-amino phosphonates under solvent-free and catalyst-free conditions . Ultrason. Sonochem. 2007 , 14 , 235 – 240 .
   PubMed Web of Science ®Google Scholar