Microwave Assisted, L-Tyrosine Catalyzed Efficient Synthesis of Tetrahydrobenzo[b] Pyrans

Authors(4) :-Balaji D. Rupnar, Sunil S. Bhagat, Amol J. Sirsat, Rajendra P. Pawar

A mild and efficient protocol has been developed for the synthesis of Tetrahydrobenzo[b]pyrans, from aldehyde, malononitrile and dimedone in presence of L-Tyrosine under Microwave irradiation. High yield, simple workup procedure and mild reaction condition are main feature of this protocol.

Authors and Affiliations

Balaji D. Rupnar
Department of Chemistry, R.B. Attal Arts, Science and Commerce College, Georai, Beed, Maharashtra,India
Sunil S. Bhagat
Department of Chemistry, Deogiri College, Aurangabad, Maharashtra,India
Amol J. Sirsat

Rajendra P. Pawar

Microwave, L-Tyrosine, Tetrahydrobenzo[B]Pyrans, Multicomponent Reaction.

  1. BriocheJ. C. R., GoodenoughK. M., Whatrup D. J.,Harrity, J. P. A., Investigation of an
  2. Organomagnesium-Based [3 + 3] Annelation to Pyrans and Its Application in the Synthesis of Rhopaloic Acid A, J. Org. Chem., 2008, 73, 1946.
  3. TapasA. R., SakarkarD. M., KakdeR. B., Flavonoids as Nutraceuticals: A Review, Trop. J.Pharm. Res., 2008, 7, 1089.
  4. GaoY.,YangW.,Du D. M., efficient organocatalytic asymmetric synthesis of 2-amino-4H-chromene-3-carbononitrile derivatives, Tetrahedron: Asymmetry 2012, 23, 339.
  5. ReynoldsG. A.,DrexhageK. H., New coumarin dyes with rigidized structure for flashlamp-pumped dye lasers,Opt. Commun, 1975, 13, 222.
  6. ZollingerH., Color Chemistry, 3rd ed.; Verlag Helvetica ChimicaActa: Zurikh and Wiley-VCH: Weinheim, 2003.
  7. BissellE. R., MitchellA. R., SmithR. E., Synthesis and chemistry of 7-amino-4-(trifluoromethyl)coumarin and its amino acid and peptide derivatives, J. Org. Chem. 1980, 45, 2283.
  8. EllisG. P., The Chemistry of Heterocyclic of Compounds. Chromenes, Harmones and Chromones; A.Weissberger,E. C. Taylor, Eds.; John Wiley: New York, NY, 1977; Chapter II, 11.
  9. Hafez E. A. A., ElnagdiM. H.,ElagameyA. G. A., El-TaweelF. M. A. A.,Nitriles in Heterocyclic Synthesis: Novel Synthesis of Benzo[c]coumarin and of Benzo[c]pyrano[3,2-c]quinoline Derivatives, Heterocycles, 1987, 26, 903.
  10. KonkoyC. S., FickD. B., CaiS. X., LanN. C.,KeanaJ. F., PCTW. Int. Appl WO 0075123, 2000; Chem. Abstr.2001, 134, 29313.
  11. BurgardA., LangH. J., GerlachU.,A new cyclic tetrapeptide composed of alternatingL-proline and 3-aminobenzoic acid subunits, Tetrahedron 1999, 55, 7555.
  12. YuN., AraminiJ. M., Germann M. W.,HuangZ., Reactions of salicylaldehydes with alkyl cyanoacetates on the surface of solid catalysts: syntheses of 4H-chromene derivatives, Tetrahedron Lett., 2000, 41(36), 6993.
  13. WlodkowicD., SkommerJ., MattoM., ErayM., PelkonenJ.,HA14-1, a small molecule Bcl-2 antagonist, induces apoptosis and modulates action of selected anticancer drugs in follicular lymphoma B cells, Leuk. Res, 2006, 30, 322-331.
  14. PanditK.S., Chavan P. V., Desai U. V., KulkarniM. A., WadgaonkarP. P.,Tris-hydroxymethylaminomethane (THAM) a novel organocatalyst for environmentally benign synthesis of medicinally important tetrahydrobenzo[b]pyrans and pyran-annulated heterocycles, New J.Chem., 2015,39, 4452.
  15. GuptaM., GuptaM., Rajnikant and GuptaV. K.,Salicyldimine-based Schiff's complex of copper(II) as an efficient catalyst for the synthesis of nitrogen and oxygen heterocycles, New J. Chem., 2015,39, 3578.
  16. CandeiasN. R., BrancoL. S. C., GoisP. M. P., AfonsoC. A. M., TrindadeA. F., More Sustainable Approaches for the Synthesis of N-Based Heterocycles, Chem. Rev., 2009, 109, 2703.
  17. YoungS. N., PsychiatryJ.,L-Tyrosine to alleviate the effects of stress?,Neurosci, 2007, 32, 224.
  18. KhaskelA., GogoiP., BarmanP., BandyopadhyayB.,Grindstone chemistry: a highly efficient and green method for synthesis of 3,4-dihydropyrimidin-2-(1H)-ones by L-tyrosine as an organocatalyst: a combined experimental and DFT study, RSC Adv, 2014, 4, 35559.
  19. ThirupathiG., VenkatanarayanaM., DubeyP. K. and BharathiKumariY., L-tyrosine catalyzed Knoevenagel condensation: Facile synthesis of cyanoacrylonitriles cyanoacrylates and cyanoacrylamides in solvent free condition under grindstone method.Der PharmaChemica, 2012, 4(5), 1897.

Publication Details

Published in : Volume 4 | Issue 3 | January-February 2018
Date of Publication : 2018-01-22
License:  This work is licensed under a Creative Commons Attribution 4.0 International License.
Page(s) : 30-34
Manuscript Number : IJSRSET184309
Publisher : Technoscience Academy

Print ISSN : 2395-1990, Online ISSN : 2394-4099

Cite This Article :

Balaji D. Rupnar, Sunil S. Bhagat, Amol J. Sirsat, Rajendra P. Pawar, " Microwave Assisted, L-Tyrosine Catalyzed Efficient Synthesis of Tetrahydrobenzo[b] Pyrans, International Journal of Scientific Research in Science, Engineering and Technology(IJSRSET), Print ISSN : 2395-1990, Online ISSN : 2394-4099, Volume 4, Issue 3, pp.30-34, January-February-2018.
Journal URL : http://ijsrset.com/IJSRSET184309

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