Keith M. Ramig

Organic Chemistry and Biochemistry

Email: Keith.Ramig@baruch.cuny.edu
Phone: (646) 660-6243
Location: Room 607, 17 Lexington Ave

Keith Ramig

Ph.D., University of Pittsburgh (1988)

Postdoctoral work, Cornell University

I began my career as an R&D chemist in the pharma industry, working on new methods for the synthesis of drug candidates.  My research since coming to Baruch in 1998 started in the area of organofluorine chemistry (synthesis of halogenated anesthetic enantiomers), and currently focuses on the study of benzazepines, which are little-studied analogues of the benzodiazepine pharmaceuticals.  Our group of undergraduate researchers devised one of the few general methods for obtaining these rare compounds, and is currently studying their properties with the eventual goal of testing their possible biological activity.  Another facet of our research deals with indigo-like dye molecules, which are well known as components of the historical dye Tyrian Purple.  Our goal is to explain the highly variable color of these dyes when they are applied to fabrics.  Both of these projects involve collaboration with professors and students at Hunter College, Queensborough Community College, and Queens College.

 

PUBLICATIONS since 1998 (* indicates a Baruch undergraduate student researcher)

K. Ramig, E. Greer, D. J. Szalda, S. Karimi, A. Ko*, L. Boulos*, J. Gu*, N. Dvorkin*, H. Bhramdat, G. Subramaniam, “NMR Spectroscopic and Computational Study of Conformational Isomerism in Substituted 2-Aryl-3H-1-Benzazepines: Toward Isolable Atropisomeric Benzazepine Enantiomers” Journal of Organic Chemistry  2013, 78:8028-8036.

K. Ramig  “Stereodynamic Properties of Medium-Ring Benzo-Fused Nitrogenous Heterocycles:  Benzodiazepines, Benzazepines, Benzazocines, and Benzazonines”  Tetrahedron 2013, 69:10783-10795.

O. Lavinda*, I. Mironova*, S. Karimi, F. Pozzi, J. Samson, H. Ajiki, L. Massa, K. Ramig “Singular Thermochromic Effects in Dyeings with Indigo, 6-Bromoindigo, and 6,6’-Dibromoindigo” Dyes and Pigments 2013, 96:581-589.

S. Karimi, K. Ramig, E. M. Greer, D. J. Szalda, W. F. Berkowitz, P. Prasad, G. Subramaniam “Tandem Ring-contraction/Decarbonylation of 2,4-Diphenyl-3H-1-benzazepine to 2,4-Diphenylquinoline” Tetrahedron  2013, 69:147-151.

K. Ramig, O. Lavinda*, D. J. Szalda “Highly Stereoselective Decarboxylation of (+)-1-Bromo-1-chloro-2,2,2-trifluoropropanoic Acid gives (+)-1-Bromo-1-chloro-2,2,2-trifluoroethane ((+)-Halothane) with Retention of Configuration” Tetrahedron: Asymmetry 2012, 23:201-204.

D. J. Szalda, K. Ramig, O. Lavinda*, Z. C. Koren, L. Massa “6-Bromoindigo Dye” Acta Cryst.  2012, C68:o160-o163.

K. Ramig, E. M. Greer, D. J. Szalda, R. Razi*, F. Mahir*, N. Pokeza*, W. Wong*, B. Kaplan*, J. Lam*, A. Mannan*, C. Missak*, D. Mai*, G. Subramaniam, W. F. Berkowitz, P. Prasad, S. Karimi, N. H. Lo, L. V. Kudzma, “Experimental and Theoretical Studies of a One-flask Synthesis of 3H-1-Benzazepines from 2-Fluoroaniline and a,b-Unsaturated Ketones” European Journal of Organic Chemistry, 2010, 2363-2371.

K. Ramig, S. Alli*, M. Cheng*, R. Leung*, R. Razi*, M. Washington*,  L. V. Kudzma “Synthesis of 2,4-Diaryl-3H-1-benzazepines” Synlett, 2007, 2868-2870.

K. Ramig, “(+/-)-Halothane (2-bromo-2-chloro-1,1,1-trifluoroethane)” Electronic Encyclopedia of Reagents for Organic Synthesis, 2007.

http://www.mrw.interscience.wiley.com/eros/articles/rn00729/frame.html

K. Ramig, "Synthesis and Reactions of Fluoroether Anesthetics." Synthesis, 2002, 2627-2631. 

              K. Ramig, M. Englander*, F. Kallashi*, L. Livchits*, J. Zhou*, "Synthesis of Esters by Selective Methanolysis of the Trifluoromethyl Group." Tetrahedron Letters, 2002, 43:7731-7734.

              L. V. Kudzma, C. G. Huang, R. A. Lessor, L. A. Rozov, S. Afrin*, F. Kallashi*, C. McCutcheon*, K. Ramig, "Diisopropylethylamine Mono(hydrogen fluoride) for Nucleophilic Fluorination of Sensitive Substrates: Synthesis of Sevoflurane." Journal of Fluorine Chemistry, 2001, 111:11-16.

R. L. Hanson, J. M. Howell, T. L. LaPorte, M. J. Donovan, D. L. Cazzulino, V. Zannella, M. A. Montana, V. B. Nanduri, S. R. Schwarz, R. F. Eiring, S. C. Durand, J. M. Wasylyk, W. L. Parker, M. S. Liu, F. J. Okuniewicz, B.-C. Chen, J. C. Harris, K. J. Natalie Jr, K. Ramig, S. Swaminathan, V. W. Rosso, S. K. Pack, B. T. Lotz, P. J. Bernot, A. Rusowicz, D. A. Lust, K. S. Tse, J. J. Venit, L. J. Szarka, R. N. Patel, “Synthesis of allysine ethylene acetal using phenylalanine dehydrogenase from Thermoactinomyces intermedius.” Enzyme and Microbial Technology, 2000, 26:348-358.

K. Ramig, L. V. Kudzma, R. A. Lessor, L. A. Rozov, "Acid Fluorides and 1,1-Difluoroethyl Methyl Ethers as Fluoride Sources in Halogen-Exchange Reactions." Journal of Fluorine Chemistry, 1999, 94:1-5.

P. L. Polavarapu, C. Zhao, K. Ramig, "Vibrational Circular Dichroism, Absolute Configuration and Predominant Conformations of Volatile Anesthetics: 1,2,2,2-Tetrafluoroethyl Methyl Ether." Tetrahedron: Asymmetry, 1999, 10:1099-1106.

L. A. Rozov, R. A. Lessor, L. V. Kudzma, and K. Ramig, "The Fluoromethyl Ether Sevoflurane as a Fluoride Source in Halogen-Exchange Reactions," Journal of Fluorine Chemistry, 1998, 88:51-54.

 

CHAPTERS IN BOOKS

K. Ramig “Asymmetric Fluoroorganic Chemistry” In P.V. Ramachandran (Ed.), Chiral Fluorinated Anesthetics American Chemical Society, 2000, pp. 282-292.

K.Ramig, D. Halpern “Asymmetric Synthesis and Resolutions of Fluorinated Volatile Anesthetics”  In V. Soloshonok (Ed.), Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets John Wiley & Sons, 1999, pp. 451-468.

 

CONFERENCE PRESENTATIONS last five years (* indicates a Baruch undergraduate student researcher)

Ramig, K. “The Flip of the Rings: Atropisomerism and Dynamic Stereochemistry in Medium-ring Nitrogen Heterocycles” Presentation at Queens College, City University of New York, 11/2013.

Mironova, I.*, Lavinda, O.*, Ramig, K., Ajiki, H., Massa, L., Karimi, S. "Reflectance Analysis and Thermochromicity of Fabrics Dyed with Indigo, 6-Bromoindigo, and 6,6’-Dibromoindigo, Components of the Ancient Dye Tyrian Purple" Presentation at the 60th Annual Undergraduate Research Symposium sponsored by the ACS, SUNY College at Old Westbury, Old Westbury, New York, NY, 5/ 2012.

Ko, A.*, Dvorkin, N.*, Boulos, L.*, Gu, J.*, Ramig, K., Greer, E., Szalda, D. J., Karimi, S., Subramaniam, G. "NMR Spectroscopic and Computational Study of Conformational Mobility in 2,4-Diaryl-3H-1-Benzazepines" Presentation at the 60th Annual Undergraduate Research Symposium sponsored by the ACS, SUNY College at Old Westbury, Old Westbury, New York, NY, 5/ 2012.

A. Ko*, N. Dvorkin*, L. Boulos*,  J. Gu*, K. Ramig, E. Greer, D. J. Szalda, S. Karimi, G. Subramaniam “NMR Spectroscopic and Computational Study of Conformational Mobility in 2-Aryl-3H-1-Benzazepines” Presentation at the Marie Curie Nobel Centennial Symposium, Baruch College, New York, NY, 11/11. 

 A. Ko*, N. Dvorkin*, L. Boulos*,  J. Gu*, K. Ramig, E. Greer, D. J. Szalda, S. Karimi, G. Subramaniam “NMR Spectroscopic and Computational Study of Conformational Mobility in 2-Aryl-3H-1-Benzazepines” Presentation at the 14th Annual Undergraduate Research Symposium in the Chemical and Biological Sciences, University of Maryland, Baltimore County, Baltimore, MD, 10/11. 

 O. Lavinda*, K. Ramig, D. J. Szalda, Z. Koren and L. Massa “Crystal Structure and Thermochromic Studies of 6-Bromoindigo” Presentation at the 42nd National Organic Symposium, Princeton University, Princeton, NJ, 6/11.

 N. Dvorkin*, L. Boulos*, J. Gu*, D. J. Szalda, E. M. Greer, K. Ramig  “Computational Analysis of Benzazepine Derivatives” Presentation at the New York Chemistry Students' Association 59th Annual Undergraduate Research Symposium,  College of Mt. Saint Vincent, Riverdale, NY, 5/7/11.

J. Gu*, L. Boulos*, N. Dvorkin*, D. J. Szalda, E. M. Greer, K. Ramig “Synthesis of 3-Alkyl-3H-1-benzazepines Via Deprotonation and Alkylation of a 3H-1-Benzazepine” Presentation at the New York Chemistry Students' Association 59th Annual Undergraduate Research Symposium,  College of Mt. Saint Vincent, Riverdale, NY, 5/7/11.

 C. Missak*, A. Mannan*, J. Lam*, E. M. Greer, K. Ramig “Factors Influencing the Isomer Distribution of Substituted 1-Benzazepines” Presentation at the New York Chemistry Students' Association 58th Annual Undergraduate Research Symposium,  Adelphi University, Garden City, NY, 5/8/10.

 J. Lam*, A. Mannan*, C. Missak*, E. M. Greer, K. Ramig “Unravelling the Mechanism of a One-flask Synthesis of Benzazepines” Presentation at the New York Chemistry Students' Association 58th Annual Undergraduate Research Symposium,  Adelphi University, Garden City, NY, 5/8/10.

 N. H. Lo, H. Bramdat, S. Karimi, G. Subramaniam, K. Ramig “1H and 13C NMR Assignments and Conformational Studies of 3H-1-Benzazepines” Presentation at the 238th American Chemical Society National Meeting, Washington, D. C., 8/09.

 N. H. Lo, S. Karimi, K. Ramig, G. Subramaniam “NMR Studies on the Conformational Exchange in 1-Benzazepines” Presentation at the 236th American Chemical Society National Meeting, Philadelphia, PA, 8/08.

 N. H. Lo, S. Karimi, K. Ramig, G. Subramaniam “NMR Studies on the Conformational Exchange in 1-Benzazepines” Presentation at the 40th American Chemical Society Mid-Atlantic Regional Meeting, Queensborough Community College, Queens, NY, 5/08.

K. Ramig, S. Alli*, M. Cheng*, R. Leung*, F. Mahir*, R. Razi*, M. Washington*, L. V. Kudzma “Synthesis of 3H-1-Benzazepines” Presentation at the 40th National Organic Symposium, Duke University, Durham, N. C., 6/07.

 R. Razi*, S. Alli*, M. Cheng*, R. Leung*, F. Mahir*, M. Washington*, K. Ramig “Synthesis of Substituted 1-Benzazepines” Presentation at the New York Chemistry Students' Association 55th Annual Undergraduate Research Symposium, Manhattan College, Bronx, NY, 5/5/07.

The City University of New York