L-Proline as an efficient enantioinduction organo-catalyst in the solvent-free synthesis of pyrazolo[3,4-b]quinoline derivatives via one-pot multi-component reaction

The role of L-proline as an efficient organo-catalyst for the three-component synthesis of pyrazoloquinolinones involving dimedone, 3-methyl-1H-pyrazol-5-amine and various aryl aldehydes under mild solvent-free condition is reported. Besides the several advantages offered by this method such as its generality, simplicity, high yields and environment friendly reaction, the most notable is the ability of the catalyst to influence asymmetric induction in the reaction. Interestingly, it was observed that in addition to being an efficient catalyst, L-proline also imparted enantioselectivity in the synthesised pyrazoloquinolinones derivatives.

[1]  G. Bez,et al.  Beyond enzymatic promiscuity: asymmetric induction by L-proline on lipase catalyzed synthesis of polyfunctionalized 4H-pyrans , 2015 .

[2]  R. Nongrum,et al.  Nickel nanoparticles assisted regioselective synthesis of pyrazoloquinolinone and triazoloquinazolinone derivatives , 2015 .

[3]  Lokman H. Choudhury,et al.  L-proline catalyzed multicomponent reactions: facile access to 2H-benzo[g]pyrazolo[3,4-b]quinoline-5,10(4H,11H)-dione derivatives , 2014 .

[4]  J. Nanubolu,et al.  Polyethylene glycol (PEG-400): an efficient and recyclable reaction medium for the synthesis of pyrazolo[3,4- b ]quinoline derivatives , 2012 .

[5]  M. R. P. Heravi,et al.  l -Proline-catalysed one-pot synthesis of tetrahydrobenzo[c]acridin-8(7H)-ones at room temperature , 2012 .

[6]  N. Al-Hokbany,et al.  Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans , 2012, Molecules.

[7]  D. Shi,et al.  Three-component one-pot synthesis of pyrazolo[3,4-b]quinolin-5(6H)-one derivatives in aqueous media , 2012 .

[8]  M. R. Rohman,et al.  l-Proline as an efficicent catalyst for the multi-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in water , 2011 .

[9]  V. N. Chernenko,et al.  Green and efficient synthesis of pyrazolo[3,4‐b]quinolin‐5‐ones derivatives by microwave‐assisted multicomponent reaction in hot water medium , 2011 .

[10]  D. Shi,et al.  An efficient synthesis of pyrazolo[3,4‐b]quinolin‐5(6H)‐one derivatives in ionic liquid , 2011 .

[11]  J. Menéndez,et al.  L-Proline-catalysed sequential four-component “on water” protocol for the synthesis of structurally complex heterocyclic ortho-quinones , 2011 .

[12]  R. Butcher,et al.  L-Proline-catalyzed one-pot expeditious synthesis of highly substituted pyridines at room temperature , 2010 .

[13]  Jianji Wang,et al.  Ionic liquid-promoted multi-component reaction: novel and efficient preparation of pyrazolo[3,4-b]pyridinone, pyrazolo[3,4-b]-quinolinone and their hybrids with pyrimidine nucleoside , 2010, Molecular Diversity.

[14]  H. Hügel.  Microwave Multicomponent Synthesis , 2009, Molecules.

[15]  X. Companyó,et al.  Organocatalytic domino reactions , 2009 .

[16]  V. N. Chernenko,et al.  Tuning of chemo- and regioselectivities in multicomponent condensations of 5-aminopyrazoles, dimedone, and aldehydes. , 2008, The Journal of organic chemistry.

[17]  M. Organ,et al.  Multicomponent reactions to form heterocycles by microwave-assisted continuous flow organic synthesis. , 2007, Journal of combinatorial chemistry.

[18]  V. N. Chernenko,et al.  One-pot, multicomponent route to pyrazoloquinolizinones. , 2007, Organic letters.

[19]  W. Jadhav,et al.  L-Proline as an Efficient Organo-Catalyst for the Synthesis of Polyhydroquinoline Via Multicomponent Hantzsch Reaction , 2007 .

[20]  S. Shishkina,et al.  Synthesis of partially hydrogenated pyrazolo[3,4-b]quinolinones by condensation of 3-amino-5-methylpyrazole with aromatic aldehydes and dimedone , 2006 .

[21]  H. Pellissier.  Asymmetric domino reactions. Part B: Reactions based on the use of chiral catalysts and biocatalysts , 2006 .

[22]  H. Pellissier.  Asymmetric domino reactions. Part A: Reactions based on the use of chiral auxiliaries , 2006 .

[23]  Y. K. Rao,et al.  Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors. , 2004, Bioorganic & medicinal chemistry letters.

[24]  B. List.  Proline-catalyzed asymmetric reactions , 2002 .

[25]  J. N. Low,et al.  Regioselective synthesis of 4,7,8,9-tetrahydro-2 H -pyrazolo[3,4- b ]quinolin-5(6 H )-ones. Mechanism and structural analysis , 2001 .

[26]  J. N. Low,et al.  4‐(4‐Methoxy­phenyl)‐3,7,7‐tri­methyl‐4,7,8,9‐tetra­hydro‐2H‐pyrazolo­[3,4‐b]quinolin‐5(6H)‐one , 2001 .

[27]  B. Insuasty,et al.  Synthesis of 4‐aryl‐4,7,8,9‐tetrahydro‐6H‐pyrazolo[3,4‐b]quinolin‐5‐ones , 1998 .

[28]  M. Pomponi,et al.  Synthesis of 7,8‐dihydro‐6H‐pyrazolo[3,4‐b]quinolin‐5‐ones and related derivatives , 1991 .

[29]  P. Siminoff,et al.  Stimulation of Interferon Production in Mice and in Mouse Spleen Leukocytes by Analogues of BL-20803 , 1977, Antimicrobial Agents and Chemotherapy.

[30]  G. M. Luke,et al.  Interferon inducing activities of derivatives of 1,3-dimethyl-4-(3-dimethylaminopropylamino)-1H-pyrazolo(3,4-b)quinoline and related compounds. , 1976, Journal of medicinal chemistry.

[31]  A. De,et al.  Synthesis and activity of a new class of heterocyclic compounds against Entamoeba histolytica. 1,2,3,3a-tetrahydro-1-alkylcyclopenta[de]quinolines. , 1970, Journal of medicinal chemistry.