Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 20
362
Views
14
CrossRef citations to date
0
Altmetric
Original Articles

Three-Component Synthesis and 1,3-Dipolar Cycloaddition of Highly Functionalized Pyrans with Nitrile Oxides: Easy Access to 1,2,4-Oxadiazoles

, , , , &
Pages 2763-2772 | Received 05 Sep 2012, Published online: 08 Jul 2013

REFERENCES

  • (a) Morinaka , Y. ; Takahashi , K. Quinolopyran-4-one-2carboxylic acid derivatives . Japan Kokai. 1977 , 17 , 498 – 507 ; (b) Montandon , J. B. ; Zijlstra , F. J. ; Wilson , J. H. P. In-vitro versus in-vivo activities of new 5-lipoxygenase inhibitors with anti-inflammatory activity . J. Int. Tissue. Reac. 1989 , 11 , 107 – 112 .
  • Konkoy , C. S. ; Fick , D. B. ; Cai , S. X. ; Lan , N. C. ; Keana , J. F. W. Substituted 5-oxo-5,6,7,8-tetrahydro-4H-1-benzopyrans and benzothiopyrans and their use as potentiators of AMPA. PCT Int. Appl. WO Patent 0075123, 2000; Chem. Abstr. 2001, 134, 29313a.
  • Tietze , L.-F. Secologanin, a biogenetic key compound—synthesis and biogenesis of the iridoid and secoiridoid glycosides . Angew. Chem., Int. Ed. Engl. 1983 , 22 , 828 – 841 , and references cited therein .
  • Hatakeyama , S. ; Ochi , N. ; Numata , H. ; Takano , S. A new route to substituted 3-methoxycarbonyldihydropyrans: Enantioselective synthesis of (–)-methyl elenolate. J. Chem. Soc., Chem. Commun. 1988, 1202–1204.
  • (a) Zhou , J. F. One-step synthesis of pyridine and 4H-pyran derivatives from bisarylidenecyclohexanone and malononitrile under microwave irradiation . Synth. Commun. 2003 , 33 , 99 – 103 ; (b) Wang , X. S. ; Shi , D. Q. ; Du , Y. ; Zhou , Y. ; Tu , S. J. Synthesis of 2-aminopyran derivatives and 3-arylpropionitrile derivatives catalyzed by KF/Al2O3 . Synth. Commun. 2004 , 34 , 1425 – 1432 ; (c) Jin , T. S. ; Liu , L. B. ; Zhao , Y. ; Li , T. S. Clean, one-pot synthesis of 4H-pyran derivatives catalyzed by hexadecyltrimethyl ammonium bromide in aqueous media . Synth. Commun. 2005 , 35 , 1859 – 1863 .
  • (a) Elnagdi , N. M. H. ; Al-Hokbany , N. S. Organocatalysis in synthesis: L-Proline as an enantioselective catalyst in the synthesis of pyrans and thiopyrans . Molecules 2012 , 17 , 4300 – 4312 ; (b) Mecadon , H. ; Rohman , M. R. ; Kharbangar , I. ; Laloo , B. M. ; Kharkongor , I. ; Rajbangshi , M. ; Myrboh , B. L-Proline as an efficient catalyst for the multicomponent synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in water . Tetrahedron Lett. 2011 , 52 , 3228 – 3231 .
  • Yao , C. ; Feng , X. ; Wang , C. ; Jiang , B. ; Yu , C. ; Wang , X. ; Li , T. ; Tu , S. Solvent-free three-component synthesis of 7-aryl-1,1-dioxothieno[3,2-b]pyran derivatives catalyzed by ammonium acetate . J. Heterocycl. Chem. 2011 , 48 , 1111 – 1116 .
  • Salfran , E. ; Suárez , M. ; Verdecia , Y. ; Alvarez , A. ; Ochoa , E. ; Martínez-Alvarez , R. ; Seoane , C. ; Martín , N. One-step synthesis of aminopyrimidines from 5-oxo-4H-benzopyrans . J. Heterocycl. Chem. 2004 , 41 , 509 – 516 .
  • Bakhite , E. A. ; Abdel-Rahman , A. E. ; Mohamed , O. S. ; Thabet , E. A. Synthesis and reactions of some new heterocyclic compounds containing the thienylthieno[2,3-b]pyridine moiety . Phosphorus, Sulfur Silicon Relat. Elem. 2004 , 179 , 1983 – 2006 .
  • Moneam , A. M. I. ; El-Dean , A. M. K. Synthesis of pyridothienopyridines and arylazothienopyridines . J. Chem. Res. 2004 , 2004 , 23 – 26 .
  • Al-Hazimi , H. M. A. ; Al-Alshaikh , M. A. Microwave-assisted synthesis of substituted furan-2-carboxaldehydes and their reactions . J. Saudi Chem. Soc. 2010 , 14 , 373 – 382 .
  • Karimi-Jaberi , Z. ; Pooladian , B. A facile synthesis of new 2-amino-4H-pyran-3-carbonitriles by a one-pot reaction of α,α′-bis(arylidene)cycloalkanones and malononitrile in the presence of K2CO3 . Sci. World J. 2012 , 2012 , 208796 .
  • Kumar , R. R. ; Perumal , S. ; Senthilkumar , P. ; Yogeeswari , P. ; Sriram , D. An atom-efficient, solvent-free, green synthesis, and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles . Bioorg. Med. Chem. Lett. 2007 , 17 , 6459 – 6462 .
  • Watjen , F. ; Baker , R. ; Engelstoff , M. ; Herbert , R. ; MacLeod , A. ; Knight , A. ; Merchant , K. ; Moseley , J. ; Saunders , J. Novel benzodiazepine receptor partial agonists: Oxadiazolylimidazobenzodiazepines . J. Med. Chem. 1989 , 32 , 2282 – 2291 .
  • Tully , W. R. ; Gardner , C. R. ; Gillespie , R. J. ; Westwood , R. 2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-a]pyrimidines as agonists and inverse agonists at benzo-diazepine receptors . J. Med. Chem. 1991 , 34 , 2060 – 2067 .
  • Saunders , J. ; Cassidy , M. ; Freedman , S. B. ; Harley , E. A. ; Iversen , L. L. ; Kneen , C. ; MacLeod , A. M. ; Merchant , K. J. ; Snow , R. J. ; Baker , R. Novel quinuclidine-based ligands for the muscarinic cholinergic receptor . J. Med. Chem. 1990 , 33 , 1128 – 1138 .
  • Orlek , B. S. ; Balaney , F. E. ; Braun , F. ; Clark , M. S. G. ; Hadley , M. S. ; Hatcher , J. ; Riley , G. J. ; Rosenberg , H. E. ; Wadsworth , H. J. ; Wyman , P. Comparison of azabicyclic esters and oxadiazoles as ligands for the muscarinic receptor . J. Med. Chem. 1991 , 34 , 2726 – 2735 .
  • Street , L. J. ; Baker , R. ; Book , T. ; Kneen , C. O. ; MacLeod , A. M. ; Merchant , K. J. ; Showell , G. A. ; Saunders , J. ; Herbert , R. H. Synthesis and biological activity of 1,2,4-oxadiazole derivatives: Highly potent and efficacious agonists for cortical muscarinic receptors. J. Med. Chem. 1990, 33, 2690–2697.
  • Swain , C. J. ; Baker , R. ; Kneen , C. ; Moseley , J. ; Saunders , J. ; Seward , E. M. ; Stevenson , G. ; Beer , M. ; Stanton , J. ; Watling , K. Novel 5-HT3 antagonists: Indole oxadiazoles . J. Med. Chem. 1991 , 34 , 140 – 151 .
  • Carbone , M. ; Li , Y. ; Irace , C. ; Mollo , E. ; Castelluccio , F. ; Di Pascale , A. ; Cimino , G. ; Santamaria , R. ; Guo , Y. W. ; Gavagnin , M. Structure and cytotoxicity of phidianidines A and B: First finding of 1,2,4-oxadiazole system in a marine natural product . Org. Lett. 2011 , 13 , 2516 – 2519 .
  • Welsch , M. E. ; Snyder , S. A. ; Stockwell , B. R. Privileged scaffolds for library design and drug discovery . Curr. Opin. Chem. Biol. 2010 , 14 , 347 – 361 .
  • Liang , G. B. ; Qian , X. Oxadiazole synthesis on solid supports . Bioorg. Med. Chem. Lett. 1999 , 9 , 2101 – 2104 .
  • Liang , G. B. ; Feng , D. D. An improved oxadiazole synthesis using peptide coupling reagents . Tetrahedron Lett. 1996 , 37 , 6627 – 6630 .
  • Young , J. R. ; DeVita , R. J. Novel synthesis of oxadiazoles via palladium catalysis . Tetrahedron Lett. 1998 , 39 , 3931 – 3934 .
  • Neidlein , R. ; Sheng , L. The syntheses of heterocyclic compounds with 1,2,4-oxadiazole as well as 1,2-pyrazole rings . Synth. Commun. 1995 , 25 , 2379 – 2394 .
  • Neidlein , R. ; Sheng , L. Syntheses of 1,2,4-oxadiazole substituted pyrazole, isoxazole, and pyrimidine heterocycles . J. Heterocycl. Chem. 1996 , 33 , 1943 – 1949 .
  • (a) Bell , C. L. ; Nambury , C. N. V. ; Bauer , L. The structure of amidoximes . J. Org. Chem. 1964 , 29 , 2873 – 2877 ; (b) Eloy , F. ; Lenaers , R. The chemistry of amidoximes and related compounds . Chem. Rev. 1962 , 62 , 155 – 183 .
  • (a) Korbonits , D. ; Horvath , K. Synthesis of heterocycles from aminoamide oximes . Heterocycles 1994 , 37 , 2051 – 2068 ; (b) Chiou , S. ; Shine , H. J. A simplified procedure for preparing 3,5-disubstituted-1,2,4-oxadiazoles by reaction of amidoximes with acyl chlorides in pyridine solution . J. Heterocycl. Chem. 1989 , 26 , 125 – 128 .
  • Gangloff , A. R. ; Litvak , J. ; Shelton , J. E. J. ; Sperandio , D. ; Wang , V. R. ; Rice , K. D. Synthesis of 3,5-disubstituted-1,2,4-oxadiazoles using tetrabutylammonium fluoride as a mild and efficient catalyst . Tetrahedron Lett. 2001 , 42 , 1441 – 1443 .
  • (a) Almansour , A. I. ; Kumar , R. S. ; Arumugam , N. ; Sriram , D. A solvent-free, four-component synthesis and 1,3-dipolar cycloaddition of 4(H)-pyrans with nitrile oxides: Synthesis and discovery of antimycobacterial activity of enantiomerically pure 1,2,4-oxadiazoles. Eur. J. Med. Chem. 2012, 53, 416–423; (b) Suresh Kumar , R. ; Osman , H. ; Perumal , S. ; Menendez , J. C. ; Ashraf Ali , M. ; Ismail , R. ; Choon , T. S. A facile three-component [3 + 2]-cycloaddition/annulation domino protocol for the regio- and diastereoselective synthesis of novel penta- and hexacyclic cage systems, involving the generation of two heterocyclic rings and five contiguous stereocenters. Tetrahedron 2011, 67, 3132–3139; (c) Suresh Kumar , R. ; Ashraf Ali , M. ; Osman , H. ; Ismail , R. ; Choon , T. S. ; Yoon , Y. K. ; Wei , A. C. ; Pandian , S. ; Manogaran , E. Synthesis and discovery of novel hexacyclic cage compounds as inhibitors of acetylcholinesterase. Bioorg. Med. Chem. Lett. 2011, 21, 3997–4000; (d) Suresh Kumar , R. ; Michael Rajesh , S. ; Perumal , S. ; Yogeeswari , P. ; Sriram , D. 1,3-Dipolar cycloaddition of nitrile oxides to (R)-1-(1-phenylethyl)-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: Synthesis and antimycobacterial evaluation of novel enantiomerically pure di- and trispiroheterocycles. Tetrahedron: Asymmetry 2010, 21, 1315–1327; (e) Kumar , R. S. ; Michael Rajesh , S. ; Perumal , S. ; Banerjee , D. ; Yogeeswari , P. ; Sriram , D. Novel three-component domino reactions of ketones, isatin, and amino acids: Synthesis and discovery of antimycobacterial activity of highly functionalized novel dispiropyrrolidines. Eur. J. Med. Chem. 2010, 45, 411–422; (f) Kumar , R. S. ; Perumal , S. ; Arun Shetty , K. ; Yogeeswari , P. ; Sriram , D. 1,3-Dipolar cycloaddition of C-aryl-N-phenylnitrones to (R)-1-(1-phenylethyl)-3-[(E)-arylmethylidene]-tetrahydro-4(1H)-pyridinones: Synthesis and antimycobacterial evaluation of enantiomerically pure spiroisoxazolidines. Eur. J. Med. Chem. 2010, 45, 124–133.
  • Bogdanowicz-Szwed , K. ; Budzowski , A. Synthesis of phenylthio substituted 4H-pyrans and 2-pyridinones by conjugate adddition-cyclisation of CH-acids to α,β-unsaturated ketones . Monatsh. Chem. 1999 , 130 , 545 – 554 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.