Dept. of Chemistry & Biochemistry

18111 Nordhoff Street
Northridge, California 91330-8241

Phone: (818) 677-1200
Fax: (818) 677-4068M
E-mail: chemistry@csun.edu

Hours:
Mon-Fri: 8:00am-5:00pm

Contact the Department Webmaster

 


Gagik G. Melikyan

Gagik G. Melikyan

PROFESSOR

Department of Chemistry and Biochemistry
California State University, Northridge
Northridge, California, 91330-8262
telephone: (818) 677-2565
e-mail:
gagik.melikyan@csun.edu
fax: (818) 677-4068

Office: Eucalyptus Hall rm 2329




Melikyan book & research website click to access file



 

EDUCATION

  • Ph.D., Institute of Elementorganic Compounds, Moscow, 1977
  • D.Sc., Institute of Organic Chemistry, Yerevan, 1990

POSTDOCTORAL APPOINTMENTS and
PROFESSIONAL EXPERIENCE

  • Alexander von Humboldt Fellow, University of Erlangen-Nurnberg, 1990-1992
  • Adjunct Professor of Chemistry, University of Oklahoma, 1993-1995

COURSES TAUGHT

  • Chemistry 103, Introductory Chemistry I
  • Chemistry 235, Introductory Organic Chemistry
  • Chemistry 331, Organic Chemistry I
  • Chemistry 331L, Organic Chemistry I Laboratory
  • Chemistry 332, Organic Chemistry II
  • Chemistry 332L, Organic Chemistry II Laboratory
  • Chemistry 333, Principles of Organic Chemistry I
  • Chemistry 333L, Principles of Organic Chemistry I Laboratory
  • Chemistry 334, Principles of Organic Chemistry II
  • Chemistry 595F, Organometallic Chemistry

RESEARCH INTERESTS

Organic / Organometallic / Medicinal Chemistry
Radical and ionic reactions of transition metal-complexed unsaturated compounds; new synthetic methodologies in organic and organometallic chemistries; computational, spectroscopic, and structural analyses of transition metal-stabilized carbocations; novel therapeutic agents for breast cancer treatment; enzymatic chemistry; aromatase metabolism; non-steroidal hormones; food chemistry; antioxidants; supplements; cosmetics; environmental chemistry.

DISTINCTIONS

  • 2008 Outstanding Faculty Award, CSUN
  • 2008 Foreign Member, National Academy of Sciences, Yerevan, Armenia
  • 2010 Jerome Richfield Scholar Award, CSUN


NSF Supported Research (2007-2010) click to access file


REPRESENTATIVE PUBLICATIONS (from a total of 81)

  • "Radical Reactions of the Cobalt-Complexed Propargyl Acetals: Inter- and Intramolecular Variants" Melikyan, G. G.; Voorhees, E.; Sepanian, R. Organometallics (2014) 33, 69-83.

  • "Impact of Reducing Agent, Temperature, and Substrate Topology on Diastereoselectivity of the Intermolecular Coupling Reactions, or How “Free” Are Cobalt-Complexed Propargyl Radicals?" Melikyan, G. G.; Carlson, L.; Sahakyan, N.; Floruti, A.; Garrison, M. Dalton Transactions (2013) 42, 14801–14812.

  • "Cobaltocene-Induced Low-Temperature Radical Coupling Reactions in a Cobalt-Alkyne Series." Melikyan, G. G.; Rivas, B.; Harutyunyan, S.; Carlson, L.; Sepanian R. Organometallics (2012) 31, 1653-1663.

  • "1,3-Steric Induction in Intermolecular Radical Reactions Mediated by a Co2(CO)6-Metal Core." Melikyan, G. G.; Spencer, R.; Rowe, A. Organometallics (2010) 29, 3556-3562.

  • "Inter- and Intramolecular Isocarbon Couplings of Cobalt-Complexed Propargyl Radicals: Challenging the Consensus." Melikyan, G. G.; Spencer, R. Tetrahedron (2010) 66, 5321-5328.

  • "Carbon Tether Rigidity as a Stereochemical Tool Directing Intramolecular Radical Cyclizations." Melikyan, G. G.; Vorhees, E.; Wild, C.; Spencer, R.; Molnar, J. Tetrahedron Letters (2010) 51, 2287-2290.

  • "Stereoselective Synthesis of meso-1,5-Cyclodecadiynes." Melikyan, G. G.; Spencer, R.; Abedi, E. J. Org. Chem. (2009) 74, 8541-8546.

  • "Cobalt-Complexed Propargyl Cations: Generation under Neutral Conditions and Spontaneous, High-Temperature Conversion to Propargyl Radicals. " Melikyan, G. G.; Sepanian, R.; Spencer, R.; Rowe, A.; Toure, P.Organometallics (2009) 28, 5541-5549.

  • "High-Temperature Reaction of a Co2(CO)6-Complexed Propargyl Cation. " Melikyan, G. G.; Mikailian, B.; Sepanian, R.; Toure, P. J. Organomet. Chem. (2009) 694, 785-794.

  • "Intramolecular Radical Cyclizations of Co2(CO)6-Complexed Propargyl Radicals: Synthesis of d,l- and meso-1,5-Cyclodecadiynes." Melikyan, G. G.; Wild, C.; Toure, P. Organometallics (2008) 27, 1569-1581.

  • "Cross-Coupling of Cobalt-Complexed Propargyl Radicals: Metal Core- and alpha- and gamma-Aryl-Induced Chemo- and Diastereoselectivity." Melikyan, G. G.; Floruti, A.; Devletyan, L.; Toure, P.; Dean, N.; Carlson, L. Organometallics (2007) 26(13), 3173-3182.

  • "Tetrahydrofuran-Mediated Stereoselective Radical C-C Bond Formation in Dicobalthexacarbonyl-Propargyl Complexes." Melikyan, G. G.; Villena, F.; Floruti, A.; Sepanian, S.; Sarkissian, H.; Rowe, A.; Toure, P.; Mehta, D.; Christian, N.; Myer, S.; Miller, D.; Scanlon, S.; Porazik, M.; Gruselle, M. Organometallics (2006) 25, 4680-4690.

  • Invited review: Gagik Melikyan. Ligand-Based Organometallic Radical Chemistry: An Emerging Interdisciplinary Field in: Frontiers in Organometallic Chemistry. Ed. M. A. Cato, Nova Science Publishers, 2006, Ch. 7, 155-190.

  • "Spontaneous Generation and Stereoselective Coupling of Co2(CO)6-Complexed Propargyl Radicals," Melikyan, G. G.; Villena, F.; Sepanian, S.; Pulido, M.; Sarkissian, H.; Floruti, A. Organic Letters (2003) 5, 3395-3397.

  • "Tetrahydrofuran - Mediated Radical Processes: Stereoselective Synthesis of dl-Hexestrol," Melikyan, G. G.; Sepanian, S.; Riahi, B.; Villena, F.; Jerome, J.; Ahrens, B.; McClain, R.; Matchett, J.; Scanlon, S.; Abrenica, E.; Paulsen, K.; Hardcastle, K. I. J. Organomet. Chem. (2003) 683(2), 324-330.

  • "Thymidine 3',5'-Diphosphoric Acid Derived Cations and Radicals: Ab Initio Study," Toure, P.; Villena, F. and Melikyan, G. G. Organic Letters (2002) 4, 3989-3992.

  • "Interaction of Propargyl Cation with Tetrahydrofuran: Thermodynamics, Kinetics, and Biological Relevance," Toure, P.; Myer, S. and Melikyan, G. G. J. Phys. Chem. A (2001) 105, 4579-4584.

  • "Hydroalumination-Brominolysis of Vinylacetylenic Alcohols: A Novel Entry to E - and Z - Bromodienols, and Bromoallenols," Gharibian, H.; Palikyan, G.; Badanyan, Sh.H.; Paulsen, K. and Melikyan, G. G. Helv. Chim. Acta. (2000) 83, 3291-3294.

  • "Manganese(II)/(III) Glycolates: Preparation, X-Ray Crystallographic Study, and Application in Radical Cycloaddition Reactions," Melikyan, G. G.; Amiryan, F.; Visi, M.; Hardcastle, K. I. and Bales, B. L. Inorg. Chim. Acta (2000) 308, 45-50.

  • "Reduction of Metal-Stabilized Alpha-CF3-Carbenium Ion Complexes under Mild Conditions: Synthesis, Structures, and Reactivity.," Gruselle, M., Malezieux, B., Andres, R., Amouri, H., Vaissermann, J. and Melikyan, G. G., Eur. J. Org. Chem. (2000), 359-368.

  • "Cobalt-Templated Radical Processes:Inter- and Intramolecular Coupling of Propargyl Radicals," Melikyan, G. G., Deravakian, A., Myer, S., Yadegar, S., Hardcastle, K. I., Ciurash, J. and Toure, P. J. Organomet. Chem. (1999) 578, 68-75.

  • "Manganese-Based Organic and Bioinorganic Transformations," Melikyan, G. G., Aldrichimica Acta (1998), 50-64.

  • "Overcoming a Longstanding Challenge: X-Ray Structure of a Co2(CO)6-Complexed Propargyl Cation," Melikyan, G. G., Bright, S., Monroe, T., Hardcastle, K. I. and Ciurash, J., Angew. Chem. (1998) 110, 170-172; Angew. Chem. Int. Ed. (1998) 37, 161-164.

  • "Tetrahydrofuran as a One-Electron Donor: Highly Diastereoselective Coupling of Cobalt-Complexed Propargyl Alcohol," Melikyan, G. G. and Deravakian, A. J. Organomet. Chem. (1997) 544, 143-145.

  • "Radical Carbon-Carbon Bond-Forming Reactions Promoted by Trivalent Manganese," Melikyan, G. G. in Organic Reactions, Ed. Paquette, L., John Wiley, 1997, Vol. 49, Ch. 3, p. 427-675.

  • "A Novel Synthetic Approach to Cycloocta-1,5-diynes and Cyclooct-3-ene-1,5-diynes," Melikyan, G. G., Khan, M.A. and Nicholas, K.M., Organometallics (1995) 14, 2170-2172.

  • "The Chemistry of Metal - Alkyne Complexes," Melikyan G. G. and Nicholas K.M. in Modern Acetylene Chemistry, Ed. Stang P.J., Diederich F., VCH Publishers, 1995, Ch. 4, 99-138.

  • "Cobalt Cluster-Directed, Mn(III)-Mediated Chemo- and Stereoselective Radical Reaction of 1-Alken-3-ynes," Melikyan, G. G., Vostrowsky, O., Bauer, W., Bestmann, H.J., Khan, M. and Nicholas, K.M., J. Org. Chem. (1994) 59, 222-229.

  • "A Novel and Efficient Synthesis of Cyclic and Acyclic 1,5-Alkadiynes by Selecitve Coupling of Co2(CO)6-Complexed Propargyl Radicals," Melikyan, G. G., Combs, R.C., Lamirand, J., Khan, M. and Nicholas, K. M., Tetrahedron Lett. (1994) 363-366.

  • "Manganese(III)-Mediated Reaction of Unsaturated Systems (Review)," Melikyan, G.G. Synthesis (1993), 833-850.

  • "µ-(3-4- -1-Alken-3-yne)Hexacarbonyldicobalt Complexes: Regioselective Radical Cyclocondensation, Mediated by Manganese(III) Acetate," Melikyan, G. G.; Vostrowsky, O., Bauer, W. and Bestmann, H. J. J. Organometal. Chem. (1992) 423, C24-C27.

  • "Dehydration of Co2(CO)6-Protected Tertiary Propargyl Alcohols. Stereo- and Regiochemistry. Synthesis of Enantiomerically Pure Manicone and Normanicone," Melikyan, G. G., Mineif, A., Vostrowsky, O. and Bestmann, H. J., Synthesis (1991) 8, 633-636.

  • "Control of the Propargyl Radical Stabilization by the Carbon-Chain Length in Manganese(III)-Mediated Reactions of 1-Alken-3ynes. A Facile Synthetic Way to Long-Chain 4-Acetoxy-5-alkynoic Acids," Melikyan, G. G., Mkrtchyan, V. M. and Badanyan, Sh. O., Vostrovsky, O. and Bestmann, H. J., Chem. Ber. (1991) 124, 2037-2040.

  • "Synthesis of (S)-(+)-Manicone and (S)-(+)-Normanicone, Mandibular Gland Constituents of Myrmicine Ants," Martischonok, V., Melikyan, G. G., Mineif, A., Vostrowsky, O. and Bestmann, H. J., Synthesis (1991), 560-564.


    M. S. THESES

    • Chiral Cobalt-Complexed Conjugated Enynes: Design, Synthesis and Radical Cycloaddition Reactions (1999) Yadegar, S.

    • Coupling Reactions of Dicobalt Hexacarbonyl Propargyl Radicals (1999) Myer, S.

    • Novel Organometallic Probes for Biochemical Studies (2001) Riahi, B.

    • Novel Reactions of Ligand-Based Organometallic Radicals (2003) Villena, F.

    • Topologically Diverse D,L-3,4-Diaryl-1,5-alkadiynes: Design, Stereoselective Synthesis and Biotesting (2006) Rowe, A.

    • Cross-Coupling of Cobalt-Complexed Propargyl Radicals: Chemo-, Regio-, and Diastereoselective Access to 3,4-Diaryl-1.5-hexadiynes (2008) Floruti, A.

    • Cobalt-Assisted Intramolecular Radical Cyclization Reactions (2008) Wild, C.

    • Inter- and Intramolecular Radical C-C Bond Formation Mediated by a Transition Metal Core (2010) Spencer, R.

    • Radical Coupling Reactions Under Neutral Conditions and Their Biological Relevance (2010) Sepanian, R.

    • Transition Metal-Mediated Radical Reactions of Propargyl Acetals (2013) Voorhees, E.