Palladium-Catalyzed 8-Exo Trig Intramolecular Heck Reaction Under Microwave Irradiation in the Presence of Basic Alumina

REFERENCES

• Alonso , F. ; Beletskaya , I. P. ; Yus , M. Nonconventional methodologies for transition metal catalyzed carbon–carbon coupling: A critical overview. Part 1: the Heck reaction . Tetrahedron 2005 , 61 , 11771 .
   Web of Science ®Google Scholar
• (a) Diederich , F. ; Stang , P. J. Eds. Metal-Catalyzed Cross Coupling Reactions ; Wiley-VCH : New York , 1998 ; (b) Tsuji , J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis ; Wiley : New York , 1995 ; (c) Kaiser , C. ; Lafferty , J. J. Piperidylidene derivatives of benzo-fused xanthenes, thioxanthenes, and dibenzoxepins and antipsychotic use thereof. U.S. Patent 4,073,912, 1972; Chem. Abstr. 1978, 89, 24156.
   Google Scholar
• Beletskaya , I. P. ; Cheprakov , A. V. The Heck reaction as a sharpening stone of palladium catalysis . Chem. Revi. 2000 , 100 , 3009
   PubMed Web of Science ®Google Scholar
• Balamurugan , R. ; Dekkerab , F. J. ; Waldmann , H. Design of compound libraries based on natural product scaffolds and protein structure similarity clustering (PSSC) . Mol. Bio. Syst. 2005 , 1 , 36 .
   Web of Science ®Google Scholar
• (a) Hermkens , P. H. H. ; Ottenheijm , H. C. J. ; Rees , D. Solid-phase organic reactions: A review of the recent literature . Tetrahedron 1996 , 52 , 4527 ; (b) Brase , S. ; Kirchhoff , J. H. ; Kobberling , J. Palladium-catalysed reactions in solid-phase organic synthesis . Tetrahedron 2003 , 59 , 885 .
   Web of Science ®Google Scholar
• (a) Bram , G. ; Loupy , A. ; Villemin , D. In olid Supports and Catalysts in Organic Synthesis ; K. Smith , (Ed.); Ellis Horwood Prentice Hall : Chichester , 1992 ; Chapter 12 , p. 302 ; (b) Varma , R. S. Solvent-free organic syntheses. Using supported reagents and microwave irradiation. Green Chem. 1999, 1, 43 .
   Google Scholar
• (a) Saha , P. ; Naskar , S. ; Paira , P. ; Hazra , A. ; Sahu , K. B. ; Paira , R. ; Banerjee , S. ; Mondal , N. B. Basic alumina–supported highly effective Suzuki–Miyaura cross-coupling reaction under microwave irradiation: Application to fused tricyclic-oxa-aza-quinolones. Green Chem. 2009, 11, 931; (b) Saha , P. ; Naskar , S. ; Paira , R. ; Mondal , S.; Maity. A. ; Sahu , K. B. ; Paira , P. ; Hazra , A. ; Bhattacharya , D. ; Banerjee , S. ; Mondal , N. B. One-pot tandem synthesis of furo[3,2-h]quinolines by a Sonogashira cross-coupling and cyclization reaction supported by basic alumina under microwave irradiation. Synthesis 2010, 3, 486.
   Web of Science ®Google Scholar
• (a) Majumdar , K. C. ; Chattopadhyay , B. ; Ray , K. Novel synthesis of medium-sized oxa-heterocycles by palladium-catalyzed intramolecular Heck reaction . Tetrahedron Lett. 2007 , 48 , 7633 ; (b) Majumdar , K. C. ; Chattopadhyay , B. ; Samanta , S. Synthesis of highly substituted dibenzoazocine derivatives by the aza-Claisen rearrangement and intramolecular Heck reaction via 8-exo-trig mode of cyclization . Tetrahedron Lett. 2009 , 50 , 3178 .
   Web of Science ®Google Scholar
• Majumdar , K. C. ; Chattopadhyay , B. Novel synthesis of nine-membered oxa-heterocycles by Pd(0)-catalyzed intramolecular Heck reaction via unusual 9-endo-trig-mode cyclization . Synlett 2008 , 7 , 979 .
   Web of Science ®Google Scholar
• (a) Park , C.-H. ; Ryabova , V. ; Seregin , I. V. ; Sromek , A. W. ; Gevorgyan , V. Palladium-catalyzed arylation and heteroarylation of indolizines . Org. Lett. 2004 , 6 , 1159 ; (b) Kalyani , D. ; Deprez , N. R. ; Desai , L. V. ; Sanford , M. S. Oxidative C−H activation/C−C bond forming reactions: synthetic scope and mechanistic insights . J. Am. Chem. Soc. 2005 , 127 , 7330 .
   PubMed Web of Science ®Google Scholar
• Majumdar , K. C. ; Maji , P. K. ; Ray , K. ; Debnath , P. Thiol mediated 8-endo-trig radical cyclization: An easy access to medium-sized cyclic ethers . Tetrahedron Lett. 2007 , 48 , 9124 .
   Web of Science ®Google Scholar
• (a) Majumdar , K. C. , Chattopadhyay , B. ; Sinha , B. Novel synthesis of oxathiocine derivatives by wittig olefination and intramolecular Heck reaction via an 8-endo-trig cyclization . Synthesis 2008 , 23 , 3857 ; (b) Majumdar , K. C. , Chattopadhyay , B. ; Sinha , B. Novel synthesis of oxocine derivatives by Wittig olefination and intramolecular Heck reaction via 8-endo trig cyclization . Tetrahedron Lett. 2008 , 49 , 1319 .
   Web of Science ®Google Scholar
• (a) Fields , J. D. ; Kropp , P. J. Surface-mediated reactions: Selective oxidation of primary and secondary amines to hydroxylamines . J. Org. Chem. 2000 , 65 , 5937 ; (b) Kotha , S. ; Mandal , K. ; Deb , A. C. ; Banerjee , S. Microwave-assisted Claisen rearrangement on a silica-gel support . Tetrahedron Lett. 2004 , 45 , 9603 .
   PubMed Web of Science ®Google Scholar
• Owczarczyk , Z. ; Lamaty , F. ; Vawter , E. J. ; Negishi , E. I. Apparent endo-mode cyclic carbopalladation with inversion of alkene configuration via exo-mode cyclization-cyclopropanation rearrangement . J. Am. Chem. Soc. 1992 , 114 , 10091 .
   Web of Science ®Google Scholar
• Denieul , M.-P. ; Skrydstrup , T. Application of an intramolecular Heck reaction for the construction of the balanol aryl core structure . Tetrahedron Lett. 1999 , 40 , 4901 .
   Web of Science ®Google Scholar
• (a) Finkelstein , J. ; Holden , K. G. ; Perchonock , C. D. Nuclear analogs of β-lactam antibiotics, V: Synthesis of a benzo-fused carbocyclic β-lactam . Tetrahedron Lett. 1978 , 19 , 1629 ; (b) Alcaide , B. ; Polanco , C. ; Sierra , M. A. A three-step general synthesis of 2-azetidinones bearing N-dehydroamino acid side chains . Eur. J. Org. Chem. 1998 , 2913 .
   Google Scholar