Room-Temperature Synthesis of Pyrazoles, Diazepines, β-Enaminones, and β-Enamino Esters Using Silica-Supported Sulfuric Acid as a Reusable Catalyst Under Solvent-Free Conditions

REFERENCES

• (a) Hatheway , G. J. ; Hansch , C. ; Kim , K. H. ; Milstein , S. R. ; Schimidt , C. L. ; Smith , R. N. ; Quin , F. R. Antitumor 1-(X-aryl)-3,3-dialkyltriazenes, 1: Quantitative structure–activity relationships vs L1210 leukemia in mice . J. Med. Chem. 1978 , 21 , 563 – 574 ; (b) Katayama , H. ; Oshiyama , T. Preparation and bioactivity of pyrazole derivativies as potential cross-linking agent . Can. J. Chem. 1997 , 75 , 913 – 919 ; (c) Badawey , E. A. M. ; El-Ashmawey , I. M. Nonsteroidal antiinflammatory agents, part 1: Antiinflammatory, analgesic, and antipyretic activity of some new 1-(pyrimidin-2-yl)-3-pyrazolin-5-ones and 2-(pyrimidin-2-yl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-ones . Eur. J. Med. Chem. 1998 , 33 , 349 – 361 ; (d) Bailey , D. M. ; Hansen , P. E. ; Hlavac , A. G. ; Baizman , E. R. ; Pearl , J. ; Defelice , A. F. ; Feigenson , M. E. 3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants . J. Med. Chem. 1985 , 28 , 256 – 260 .
   Web of Science ®Google Scholar
• (a) Edafiogho , I. O. ; Moore , J. A. ; Alexander , M. S. ; Scott , K. R. Nuclear magnetic resonance studies of anticonvulsant enaminones. J. Pharm. Sci. 1994, 83, 1155–1170; (b) Foster , J. E. ; Nicholson , J. M. ; Butcher , R. ; Stables , J. P. ; Edafiogho , I. O. ; Goodwin , A. M. ; Henson , M. C. ; Smith , C. A. ; Scott , K. R. Synthesis, characterization, and anticonvulsant activity of enaminones, part 6: Synthesis of substituted vinylic benzamides as potential anticonvulsants. Bioorg. Med. Chem. 1999, 7, 2415–2425; (c) Wang , Y. F. ; Izawa , T. ; Kobayashi , S. ; Ohno , M. Stereocontrolled synthesis of (+)-negamycin from an acyclic homoallylamine by 1,3-asymmetric induction. J. Am. Chme. Soc. 1982, 104, 6465–6466; (d) Michael , J. P. ; De Koning , C. B. ; Hosken , G. D. ; Stanbury , T. V. Reformatsky reactions with N-arylpyrrolidine-2-thiones: Synthesis of tricyclic analogues of quinolone antibacterial agents. Tetahedron 2001, 57, 9635–9648; (e) Boger , D. L. ; Ishizaki , T. ; Wysocki , R. J. ; Munk , J. S. A. ; Kitos , P. A. ; Suntornwat , O. Total synthesis and evaluation of (±)-N-(tert-butoxycarbonyl)-CBI, (±)-CBI-CDPI1, and (±)-CBI-CDPI2: CC-1065 functional agents incorporating the equivalent 1,2,9,9a-tetrahydrocyclopropa[1,2-c]benz[1,2-e]indol-4-one (CBI) left-hand subunit. J. Am. Chem. Soc. 1989, 111, 6461–6463.
   PubMed Web of Science ®Google Scholar
• Spivey , A. C. ; Srikaran , R. ; Diaper , C. M. ; Turner , D. J. Traceless solid phase synthesis of 2-substituted pyrimidines using an “off-the-shelf” chlorogermane-functionalised resin . Org. Biomol. Chem. 2003 , 1 , 1638 – 1640 .
   PubMed Web of Science ®Google Scholar
• (a) Polshettiwar , V. ; Varma , R. S. Greener and rapid access to bio-active heterocycles: Room temperature synthesis of pyrazoles and diazepines in aqueous medium . Tetrahedron Lett. 2008 , 49 , 397 – 400 ; (b) Wang , Z. ; Qin , H. Solventless synthesis of pyrazole derivatives . Green Chem. 2004 , 6 , 90 – 92 ; (c) Mohamed Ahmed , M. S. ; Kobayashi , K. ; Mori , A. One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling . Org. Lett. 2005 , 7 , 4487 – 4489 ; (d) Heller , S. T. ; Natarajan , S. R. 1,3-Diketones from acid chlorides and ketones: A rapid and general one-pot synthesis of pyrazoles . Org. Lett. 2006 , 8 , 2675 – 2678 ; (e) Deng , X. ; Mani , N. S. Reaction of N-monosubstituted hydrazones with nitroolefins: A novel regioselective pyrazole synthesis . Org. Lett. 2006 , 8 , 3505 – 3508 ; (f) Armstrong , A. ; Jones , L. H. ; Knight , J. D. ; Kelsey , R. D. Oxaziridine-mediated amination of primary amines: Scope and application to a one-pot pyrazole synthesis . Org. Lett. 2005 , 7 , 713 – 716 ; (g) Greenberg , S. ; Marcuccio , S. M. ; Leznoff , C. C. ; Tomer , K. B. Selective synthesis of binuclear and trinuclear phthalocyanines covalently linked by a one atom oxygen bridge . Synthesis 1986 , 409 ; (h) Siva , A. ; Murugan , E. A new trimeric cinchona alkaloid as a chiral phase-transfer catalyst for the synthesis of asymmetric α-amino acids . Synlett 2005 , 2927 .
   Web of Science ®Google Scholar
• (a) Rault , S. ; Gillard , A. C. ; Foloppe , M. P. ; Robba , M. A new rearrangement under microwave heating conditions: Synthesis of cyclopenta[b][1,4]benzodiazepines and tetrahydrodibenzo[b,f][1,4]diazepines . Tetrahedron Lett. 1995 , 36 , 6673 – 6674 ; (b) Eary , C. T. ; Clausen , D. Preparation of substituted 1,2,3,4-tetrahydroquinoxalines and 2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepines from catalytic Cp∗Ir hydrogen transfer N-heterocyclization of anilino alcohols . Tetrahedron Lett. 2006 , 47 , 6899 – 6902 ; (c) Wang , Q. F. ; Hu , B. ; Luo , B. H. ; Hu , C. M. Synthesis of 5-per(poly)fluoroalkyl-2,3-dihydro-1,4-diazepines . Tetrahedron Lett. 39 , 2377 – 2380 ; (d) Bonacorso , H. G. ; Lourega , R. V. ; Deon , E. D. ; Zanatta , N. ; Martins , M. A. P. The first synthesis of dihydro-3H-pyrido[2,3-b][1,4]diazepinols and a new alternative approach for diazepinone analogues . Tetrahedron Lett. 2007 , 48 , 4835 – 4838 ; (e) Cairns , J. ; Clarkson , T. R. ; Hamersma , J. A. M. ; Rae , D. R. 11-(Tetrahydro-3 and 4-pyridinyl)dibenzo[b,e][1,4]diazepines undergo novel rearrangements on treatment with concentrated HBr . Tetrahedron Lett. 2002 , 43 , 1583 – 1585 .
   Web of Science ®Google Scholar
• (a) Rechsteiner , B. ; Texier-Boullet , F. ; Hamalin , J. Synthesis in dry media coupled with microwave irradiation: Application to the preparation of enaminoketones. Synthesis in dry media coupled with microwave irradiation: Application to the preparation of enaminoketones . Tetrahedron Lett. 1993 , 34 , 5071 – 5074 ; (b) Braibante , M. E. F. ; Braibante , S. ; Missio , L. ; Andricopulo , A. Synthesis and reactivity of β-amino α,β-unsaturated ketones and esters using K-10 montmorillonite . Synthesis 1994 , 898 ; (c) Arcadi , A. ; Bianchi , G. ; Di Giuseppe , S. ; Marinelli , F. Gold catalysis in the reactions of 1,3-dicarbonyls with nucleophiles . Green Chem. 2003 , 5 , 64 – 67 ; (d) Khosropour , A. R. ; Khodaei , M. M. ; Kookhazadeh , M. A mild, efficient and environmentally friendly method for the regio- and chemoselective synthesis of enaminones using Bi(TFA)3 as a reusable catalyst in aqueous media . Tetrahedron Lett. 2004 , 45 , 1725 – 1728 ; (e) Bartoli , G. ; Bosco , M. ; Locatelli , M. ; Marcantoni , E. ; Melchiorre , P. ; Sambri , L. Zn(ClO4)2·6H2O as a powerful catalyst for the conversion of β-Ketoesters into β-enamino esters . Synlett 2004 , 239 ; (f) Khodaei , M. M. ; Khosropour , A. R. ; Kookhazadeh , M. Enamination of β-dicarbonyl compounds catalyzed by CeCl3·7H2O at ambient conditions: Ionic liquid and solvent-free media . Synlett 2004 , 1980 ; (g) Das , B. ; Venkateswarlu , K. ; Majhi , A. ; Reddy , M. R. ; Reddy , K. N. ; Rao , Y. K. ; Ravikumar , K. ; Sridhar , B. Highly efficient, mild and chemo- and stereoselective synthesis of enaminones and enamino esters using silica supported perchloric acid under solvent-free conditions . J. Mol. Catal. A: Chem. 2006 , 246 , 276 – 281 .
   Web of Science ®Google Scholar
• (a) Cave , G. W. V. ; Raston , C. L. ; Scott , J. L. Recent advances in solventless organic reactions: Towards benign synthesis with remarkable versatility . Tetrahedron Lett. 2001 , 1 , 2159 – 2169 ; (b) Raston , C. L. ; Scott , J. L. Chemoselective, solvent-free aldol condensation reaction . Green Chem. 2000 , 2 , 49 – 52 ; (c) Yoshizawa , K. ; Toyota , S. ; Toda , F. Solvent-free Claisen and Cannizzaro reactions . Tetrahedron Lett. 2001 , 42 , 7983 – 7985 ; (d) Tanaka , K. ; Sugino , T. ; Toda , F. Selective Stobbe condensation under solvent-free conditions . Green Chem. 2000 , 2 , 303 – 304 ; (e) Yoshizawa , K. ; Toyota , S. ; Toda , F. Efficient solvent-free Thorpe reactions . Green Chem. 2002 , 4 , 68 – 70 .
   Google Scholar
• (a) Rajput , V. K. ; Roy , B. ; Mukhopadhyay , B. Sulfuric acid immobilized on silica: An efficient reusable catalyst for selective hydrolysis of the terminal O-isopropylidene group of sugar derivatives . Tetrahedron Lett. 2006 , 47 , 6987 – 6991 ; (b) Roy , B. ; Mukhopadhyay , B. Sulfuric acid immobilized on silica: An excellent catalyst for Fischer type glycosylation . Tetrahedron Lett. 2007 , 48 , 3783 – 3787 .
   Web of Science ®Google Scholar
• Das , B. ; Veeranjaneyulu , B. ; Krishnaiah , M. ; Balasubramanyam , P. Synthesis of gem-dihydroperoxides from ketones using silica-supported sodium hydrogen sulfate as a heterogeneous catalyst. J. Mol. Catal. A: Chem. 2008, 284, 116–119.
   Web of Science ®Google Scholar