The Noland Research Group | Department of Chemistry

Principal Research Interests

Research in Professor Noland’s group is focused on heterocyclic nitrogen and/or sulfur chemistry, including the chemistry of nitro compounds, with emphasis on synthesis, mechanisms, and submission of compounds for testing for medicinal activity. To date, activity has been found against cancer (in two classes of compounds), AIDS, tuberculosis, and plants, including fungi. Currently, emphasis is also being placed on the synthesis of benzofurazan oxides, nitriles, isonitriles, and their analogs, to observe interactions, especially with halogens, in the crystalline state. This is being carried out in a fruitful collaboration with the late-Professor Emeritus Doyle Britton, who founded the department’s X-ray crystallographic laboratory.

Noland Group-2017

Recent Publications and News Items

Synthesis of Vinylindoles and Vinylpyrroles by the Peterson Olefination or by Use of the Nysted Reagent

Noland, W. E.; Etienne, C. L.; Lanzatella, N. P. J. Heterocycl. Chem. 2011, 48, 381.

Reductive Amination of Tryptophan; Dimethyltryptophan

Schneerer, A.; Olson, N.; Noland, W.E. ChemSpider Synthetic Pages, 2017, 830, 1.

Synthesis and crystallography of 8-halonaphthalene-1-carbonitriles and naphthalene-1,8-dicarbonitrile

Noland, W. E.; Narina, V. S.; Britton, D. J. Chem. Res. 2011, 35, 694.

A 2:1 co-crystal of 3,5-dibromo-4-cyanobenzoic acid and anthracene

Noland, W. E.; Rieger, J. R.; Tua, Z. H.; Tritch, K. J. Acta Crystallographica Section E , 2017, 73, 1743-1746.

Four polymorphs (polytypes) of 5,6-dimethylbenzofurazan 1-oxide

Britton, D.; Young, V. G.; Noland, W. E.; Pinnow, M. J.; Clark, C. M. Acta Cryst. Sect. B, 2012, 68, 536.

2,6-Dibromo-4-nitrobenzonitrile

Noland. W. E and Tritcha. K. J. IUCrData, 2017, 2, x171617, 1-3

Access to Indoles via Diels–Alder Reactions of 5-Methylthio-2-vinylpyrroles with Maleimides

Noland, W. E.; Lanzatella, N. P.; Dickson, R. R.; Messner, M. E.; Nguyen, H. H. J. Heterocycl. Chem. 2013, 50, 795.

Cyclo-alkylation of the primary amine of tryptophan methyl ester to a pyrrolidine; Methyl 3-(1H-indol-3-yl)-2-(pyrrolidin-1-yl)propanoate

Schneerer, A.; Olson, N.; Noland. W. E. ChemSpider Synthetic Page, 2017, 831

Crystal structure of (±)-(3aR,5R,8bR)-5-hydroperoxy-2-phenyl-6-tosyl-4,5,6,8b-tetrahydropyrrolo[3,4-e]indole-1,3(2H,3aH)-dione

Noland, W. E.; Gullickson, G. C.; Dickson, R. R.; Groess, L. L.; Tritch, K. J. Acta Crystallogr. Sect. E, 2014, 70, 192.

Crystal structures of 2,6-dibromo-4-methylbenzo- nitrile and 2,6-dibromo-4-methylphenyl isocyanide

Noland. W. E.; Shudy, J. E.; Rieger. J. L.;Tu. H. Z.;Tritch. K. J. ActaCryst. E. 2017, E73, 1913–1916

Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diazapentacyclo[5.5.5.01,16.02,6.08,12]heptadeca-13,16-diene-3,5,9,11-tetrone p-xylene hemisolvate

Noland, W. E.; Kroll, N. J.; Huisenga, M. P.; Yue, R. A.; Lang, S. B.; Klein, N. D.; Tritch, K. J. Acta Crystallogr. Sect. E, 2014, 70, 550.

Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid

Noland, W. E.; Brown, C. D.; Bisel, A. M.; Schneerer, A. K.; Tritch, K. J. Acta Crystallogr. Sect. E, 2015, 71, 1414.

Crystal structure of rac-(3a'R,9a'R)-3a'-(indol-3-yl)-1′,2′,3′,3a',4′,9a'-hexahydrospiro[cyclopentane-1,9′-pentaleno[1,2-b]indole] p-xylene hemisolvate

Noland, W. E.; Worth, M. A.; Schneerer, A. K.; Paal, C. L.; Tritch, K. J. Acta Crystallogr. Sect. E 2015, 71, 516.

Two new polytypes of 2,4,6-tribromobenzonitrile

ritton, D.; Noland, W. E.; Tritch, K. J. Acta Crystallogr. Sect. E, 2016, 72, 178.

N′-Acylation of (3,2′)-indole dimers

Noland, W. E.; Kumar, H. V.; Lu, C.; Brown, C. D.; Wiley-Schaber, E.; Johansson, A.; LaBelle, E. V.; O'Brian, N. C.; Jensen, R. C.; Tritch, K. J. Tetrahedron Letters. 2016, 57, 2158

Diels-alder reactions of 2-(2-nitroethenyl)-1H-pyrroles and their oxygen and sulfur analogs with quinones

Noland, W. E.; Pardi, G. J. Heterocycl. Chem. 2005, 42, 1149.

The Structure of Crystalline Agnotobenzaldehyde

Noland, W. E.; Gullickson, G. C.; van Lengerich, H.; Erdman, P. J.; Tritch, K. J. J. Chem. Crystallogr. 2017, 47, 80.

Synthesis of 5-Substituted 4,5,6,7-Tetrahydroindoles from Cyclohexanones

Lee, C. K.; Lee, I. S. H.; Noland, W. E. Heterocycles 2007, 71, 419

Hydrated ferric sulfate-catalyzed reactions of indole with aldehydes, ketones, cyclic ketones, and chromanones: Synthesis of bisindoles and trisindoles

Noland, W. E.; Kumar, H. V.; Flick, G. C.; Aspros, C. L.; Yoon, J. H.; Wilt, A. C.; Dehkordi, N.; Thao, S.; Schneerer, A. K.; Gao, S.; Tritch, K. J. Tetrahedron, 2017, 73, 3913.

5-Iodobenzofurazan 1-oxide: polymorphs, pseudosymmetry and disorder

Britton, D.; Noland, W. E.; Clark, C. M. Acta Cryst. Sect. C, 2008, 64, o187.

Methylation of Cyclohexane-1,3-dione at the C2-Position; 2,2-Dimethylcyclohexane-1,3-dione

Tritch, K. J.; Brown, C. D.; Shudy, J. E.; Noland, W. E. ChemSpider Synthetic Pages 2017, 813, 1.

Access to indoles via Diels-Alder reactions of 3-vinylpyrroles

Noland, W. E.; Lanzatella, N. P. J. Heterocycl. Chem. 2009, 46, 1285.

Bis(phenylhydrazones) derived from 2,2-dialkyl cyclohexane-1,3-diones; 1E,1’E-(2,2-Dimethylcyclohexane-1,3-diylidene)bis(2-phenylhydrazine); 1E,1’E-(Spiro[4.5]decane-6,10-diylidene)bis(2-phenylhydrazine)

Tritch, K. J.; Capek, J. A.; Klein, N. D.; Noland, W. E. ChemSpider Synthetic Pages 2017, 815, 1.

In Situ Vinylpyrrole Synthesis. Diels-Alder Reactions with Maleimides to Give Tetrahydroindoles

Noland, W. E.; Lanzatella, N. P.; Sizova, E. P.; Venkatraman, L.; Afanasyev, O. V. J. Heterocycl. Chem. 2009, 46, 503.

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