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BITS Pilani
Pilani Campus
Povarov-Reductive Amination Cascade to Access
6-Aminoquinolines and Anthrazolines
Kasiviswanadha...
BITS Pilani, Pilani Campus
 Introduction
 Results and Discussion
 Conclusion
 Acknowledgements
Contents of the Seminar...
BITS Pilani, Pilani Campus
3
Quinolines derivatives
BITS Pilani, Pilani Campus
Lit. for the synthesis of Anthrazolines
Ref# 1) Eilaf Ahmed , Alejandro L. Briseno , Younan Xia...
BITS Pilani, Pilani Campus
Povarov reaction
Ref# L. S. Povarov, Russian. Chem. Rev, 1967, 36, 656.
5
BITS Pilani, Pilani Campus
Imine as oxidizing agent
Ref# R. Leardini, D. Nanni, A. Tundo, G. Zanardi, F. Ruggieri, J. Org....
BITS Pilani, Pilani Campus
Imine as oxidizing agent
Ref# N. Shindoh, H. Tokuyama, Y. Takemoto and K. Takasu, J. Org. Chem,...
BITS Pilani, Pilani Campus
Imine as oxidizing agent
Ref# V. Gaddam, S. Ramesh and R. Nagarajan, Tetrahedron, 2010, 66, 421...
BITS Pilani, Pilani Campus
Our approach
9
BITS Pilani, Pilani Campus
Our approach
10
BITS Pilani, Pilani Campus
11
BITS Pilani, Pilani Campus
BITS Pilani, Pilani Campus
BITS Pilani, Pilani Campus
Entry Catalyst Solvent Yieldb
1 BF3-Et2O CH3CN 36
2 BF3-Et2O CH3CN 44c
3 AlCl3 CH3CN 22
4 p-TSA...
BITS Pilani, Pilani Campus
Diversifying the methodology
15
BITS Pilani, Pilani Campus
Diversifying the methodology
16
BITS Pilani, Pilani Campus
Utility of new compounds
17
BITS Pilani, Pilani Campus
18
BITS Pilani, Pilani Campus
• A new tandem multicomponent approach has been introduced for the
synthesis N-arylmethyl-6-ami...
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Kasiviswanadharaju pericherla, tandem povarov reaction, hydrogen transfer

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this ppt represents recently published organic letters for the tandem synthesis of aminoquinolines derivatives via povarov reaction and hydrogen transfer

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Kasiviswanadharaju pericherla, tandem povarov reaction, hydrogen transfer

  1. 1. BITS Pilani Pilani Campus Povarov-Reductive Amination Cascade to Access 6-Aminoquinolines and Anthrazolines Kasiviswanadharaju Pericherla, August 30, 2013
  2. 2. BITS Pilani, Pilani Campus  Introduction  Results and Discussion  Conclusion  Acknowledgements Contents of the Seminar 2
  3. 3. BITS Pilani, Pilani Campus 3 Quinolines derivatives
  4. 4. BITS Pilani, Pilani Campus Lit. for the synthesis of Anthrazolines Ref# 1) Eilaf Ahmed , Alejandro L. Briseno , Younan Xia ,and Samson A. Jenekhe, J. Am. Chem. Soc. 2008, 130, 1118. 2) Christopher J. Tonzola , Maksudul M. Alam , Werner Kaminsky , and Samson A. Jenekhe,J. Am. Chem. Soc. 2003, 125, 13548. 4
  5. 5. BITS Pilani, Pilani Campus Povarov reaction Ref# L. S. Povarov, Russian. Chem. Rev, 1967, 36, 656. 5
  6. 6. BITS Pilani, Pilani Campus Imine as oxidizing agent Ref# R. Leardini, D. Nanni, A. Tundo, G. Zanardi, F. Ruggieri, J. Org. Chem, 1992, 57, 1842. 6
  7. 7. BITS Pilani, Pilani Campus Imine as oxidizing agent Ref# N. Shindoh, H. Tokuyama, Y. Takemoto and K. Takasu, J. Org. Chem, 2008, 73, 7451. 7
  8. 8. BITS Pilani, Pilani Campus Imine as oxidizing agent Ref# V. Gaddam, S. Ramesh and R. Nagarajan, Tetrahedron, 2010, 66, 4218. 8
  9. 9. BITS Pilani, Pilani Campus Our approach 9
  10. 10. BITS Pilani, Pilani Campus Our approach 10
  11. 11. BITS Pilani, Pilani Campus 11
  12. 12. BITS Pilani, Pilani Campus
  13. 13. BITS Pilani, Pilani Campus
  14. 14. BITS Pilani, Pilani Campus Entry Catalyst Solvent Yieldb 1 BF3-Et2O CH3CN 36 2 BF3-Et2O CH3CN 44c 3 AlCl3 CH3CN 22 4 p-TSA CH3CN 18 5 CF3CO2H CH3CN trace 6 CH3CO2H CH3CN NDd 7 Sc(OTf)3 CH3CN 39 8 Cu(OTf)2 CH3CN 22 9 Y(OTf)3 CH3CN 29 10 Yb(OTf)3 CH3CN 48 11 CANe CH3CN 16 12 Cyanuric chloride CH3CN 12 13 Yb(OTf)3 1,4-Dioxane 15 14 Yb(OTf)3 Toluene NDd 15 Yb(OTf)3 DCEf 18 16 Yb(OTf)3 DMFg NDd 17 Yb(OTf)3 DMEh trace aReaction conditions: 1 (1.0 mmol), 2 (2.0 mmol), 3 (1.5 mmol), Catalyst (0.05 mmol), Solvent (3.0 mL), 80 °C, 14 h. bIsolated yields. cCatalyst (20 mol%). dNot Detected. eCeric ammonium nitrate. f1,2-Dichloroethane. gN,N-Dimethylformamide. h1,2-Dimethoxyethane Optimization 14
  15. 15. BITS Pilani, Pilani Campus Diversifying the methodology 15
  16. 16. BITS Pilani, Pilani Campus Diversifying the methodology 16
  17. 17. BITS Pilani, Pilani Campus Utility of new compounds 17
  18. 18. BITS Pilani, Pilani Campus 18
  19. 19. BITS Pilani, Pilani Campus • A new tandem multicomponent approach has been introduced for the synthesis N-arylmethyl-6-amino-2,4-diarylquinolines via Povarov reaction, dehydrogenation and imine reduction. • An array of 6-aminoquinoline derivatives have been synthesized to demonstrate the scope of the standardized condition. • Removal of the N-benzyl group on a representative molecule by catalytic hydrogenation resulted in 6-amino-2,4-diphenylquinoline, which was utilized in making symmetrical and unsymmetrical anthrazoline derivatives. • This work represents the first report for the synthesis unsymmetrical anthrazolines using 1,4-phenylenediamine. Conclusion 19

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