Mild and Simple Access to Diverse 4-Amino-substituted 2-Phenyl-1,2,3,4-tetrahydroquinolines and 2-Phenylquinolines Based on a Multicomponent Imino Diels–Alder Reaction

REFERENCES

• Manske , R. H. F. ; Kukla , M. The skraup synthesis of quinoline . Org. React. 1953 , 7 , 59 .
   Google Scholar
• Bergstrom , F. W. Heterocyclic nitrogen compounds, part IIA: Hexacyclic compounds: Pyridine, quinoline, and isoquinoline . Chem. Rev. 1944 , 35 , 153 .
   Google Scholar
• Cheng , C.-C. ; Yan , S.-J. Review on Friedländer quinoline synthesis . Org. React. 1982 , 28 , 37 .
   Web of Science ®Google Scholar
• Jones , G. ; Weissberger , A. ; Taylor , E. C. (Eds.). Chemistry of Heterocyclic Compounds ; John Wiley and Sons : Chichester , 1977 ; vol. 32 , pp. 93 – 318 .
   Google Scholar
• Reitsema , R. H. The chemistry of 4-hydroxyquinolines . Chem. Rev. 1948 , 43 , 47 .
   Google Scholar
• Bergstrom , F. W. Heterocyclic nitrogen compounds, part IIA: Hexacyclic compounds: Pyridine, quinoline, and isoquinoline . Chem. Rev. 1944 , 35 , 156 .
   Google Scholar
• Jones , G. ; Katritzky , A. R. ; Rees , C. W. ; Scriven , E. E. (Eds.). In Comprehensive heterocyclic chemistry ; Pergamon Press : Oxford , 1996 ; vol. 5 , p. 167 .
   Google Scholar
• Boger , D. L. ; Weinreb , S. M. Hetero-Diels–Alder Methodology in Organic Synthesis ; Academic Press : San Diego , 1987 .
   Google Scholar
• Buonora , P. ; Olsen , J.-C. ; Oh , T. Recent developments in imino-Diels–Alder reactions . Tetrahedron 2001 , 57 , 6099 .
   Web of Science ®Google Scholar
• (a) Povarov , L. S. α,β-Unsaturated ethers and their analogues in reactions of diene synthesis. Russ. Chem. Rev. 1967, 36, 656; (b) Grieco , P. A. ; Bahsas , A. Role reversal in the cyclocondensation of cyclopentadiene with heterodienophiles derived from aryl amines and aldehydes: Synthesis of novel tetrahydroquinolines. Tetrahedron Lett. 1988, 29, 5855.
   Google Scholar
• Babu , G. ; Perumal , P. T. Synthetic applications of indium trichloride–catalyzed reactions . Aldrichm. Acta 2000 , 33 , 16 .
   Web of Science ®Google Scholar
• Kobayashi , S. Scandium triflate in organic synthesis . Eur. J. Org. Chem. 1999 , 15 .
   Web of Science ®Google Scholar
• Stevenson , P. J. ; Niuwenhuyzen , M. ; Osborne , D. Three-component coupling reactions of N-acetyl-2-azetine-rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines . Chem. Commun. 2002 , 444 .
   PubMedGoogle Scholar
• Sunderanrajan , G. ; Prabagaran , N. ; Varghese , B. First asymmetric synthesis of quinoline derivatives by inverse electron demand (IED) Diels−Alder reaction using chiral Ti(IV) complex . Org. Lett. 2001 , 3 , 1973 .
   PubMedGoogle Scholar
• Ma , Y. ; Qian , C. ; Xie , M. ; Sun , J. Lanthanide chloride–catalyzed imino-Diels−Alder reaction: One-pot synthesis of pyrano[3,2-c]- and furo[3,2-c]quinolines . J. Org. Chem. 1999 , 64 , 6462 .
   Web of Science ®Google Scholar
• (a) Toy , A. D. F. ; Walsh , E. N. In Phosphorus Chemistry in Everyday Living ; American Chemical Society : Washington , D.C. , 1987 ; (b) Engel , R. In Handbook of Organophosphorus Chemistry ; Marcel Dekker : New York , 1992 .
   Google Scholar
• Han , B. ; Jia , X.-D. ; Jin , X.-L. ; Zhou , Y.-L. ; Yang , L. ; Liu , Z.-L. ; Yu , W. A CAN-initiated aza-Diels–Alder reaction for a facile synthesis of 4-amido-N-yl tetrahydroquinolines . Tetrahedron. Lett. 2006 , 47 , 3545 – 3547 .
   Web of Science ®Google Scholar
• Kouznetsov , V. V. ; Bohorquez , A. R. R. ; Saavedra , L. A. ; Medina , R. F. An efficient synthesis of new C-2 aryl substituted quinolines based on three-component imino-Diels-Alder reaction . Mol. Diver. 2006 , 10 , 29 – 37 .
   PubMed Web of Science ®Google Scholar
• Jia , X. ; Han , B. ; Zhang , W. ; Jin , X. ; Yang , Li. ; Liu , Z.-L. Cation radical aza-Diels–Alder reaction between N-arylimines and N-vinyllactams: A facile synthesis of 4-lactam-N-yl tetrahydroquinolines . Synthesis 2006 , 17 , 2831 – 2836
   Google Scholar
• Srinivasa , A. ; Mahadevan , K. M. ; Hulikal , V. Imino Diels–Alder reactions: Efficient synthesis of 2-aryl-4-(29-oxopyrrolidinyl-19)-1,2,3,4-tetrahydroquinolines catalysed by antimony(III) sulphate . Monatsh. Chem. 2008 , 139 , 255 – 259 .
   Web of Science ®Google Scholar
• Srinivasa , A. ; Mahadevan , K. M. ; Hulikal , V. Synthesis of 1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-ones from anilines and N-vinyl pyrro lidin-2-one through imino Diels–Alder reaction using 4-nitro phthalic acid as catalyst . Synth. Commun. 2009 , 39 , 1 – 9 .
   Google Scholar