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

Two new polytypes of 2,4,6-tribromobenzonitrile

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

Crystal structures of methyl 3,5-di-bromo-4-cyano-benzoate and methyl 3,5-di-bromo-4-iso-cyano-benzoate

Noland WE, Herzig RJ, Engwall AJ, Jensen RC, Tritch KJ. Acta Crystallogr E Crystallogr Commun. 2018, 13;74(Pt 3):345-348

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

2,6-Dibromo-4-chlorophenyl isocyanide

Noland WE and Tritch KJ

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 2-(9H-carbazol-1-yl)anilines from 2,3′-biindolyl and ketones

Noland WE, Brown CD, Zabronsky AE, Tritch KJ, Tetrahedron, 2018, 74, 2391-2404

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.

Crystal structures of methyl 3,5-di-bromo-4-cyano-benzoate and methyl 3,5-di-bromo-4-iso-cyano-benzoate

Noland WE, Herzig RJ, Engwall AJ, Jensen RC, Tritch KJ. Acta Crystallogr E Crystallogr Commun. 2018, 13;74(Pt 3):345-348.

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.

2,6-Dibromo-4-chlorophenyl isocyanide

Noland WE and Tritcha KJ, IUCrData, 2018, 3, x171819

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.

Condensation reactions of indole with acetophenones affording mixtures of 3,3-(1-phenylethane-1,1-diyl)bis(1H-indoles) and 1,2,3,4-tetrahydro-3-(1H-indol-3-yl)-1-methyl-1,3-diphenylcyclopent[b]indoles

Noland WE, Brown CD, DeKruif RD, Lanzatella NP, Gao SM, Zabronsky AE, Tritch KJ, Synthetic Communications, 2018, 48, 1755-1765

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.

Methylation of Dimedone at the C2-Position; 2,2,5,5-Tetramethylcyclohexane-1,3-dione

Tritch, K. J.; Dix, S. E.; Rieger, J. L.; Noland, W. E. ChemSpider Synthetic Pages 2017, 814, 1.

A Diels–Alder/Ene Cascade Leading to 5‐(Pyrrolidin‐3‐yl)thieno[3,2‐e]isoindoles from Ketone‐derived 2‐Vinylthiophenes and N‐Phenylmaleimide

Noland WE, Huisenga, MP, Herzig RJ, JA Rosenow, H Kim, Kroll NJ, Nesmelov A, Johnson BT, Duncan NS.

Ratanayanon J, Yue RA, Xiong K, Ong BK, Vo DT, Klein ND, Lang SB, Riley JK, Daniels SP, Tritch KJ. Journal of Heterocyclic Chemistry, 2018, 55, 2698-2714

Access to Indoles via Diels-Alder Reactions of 2-Vinylpyrroles with Maleimides

Noland, W. E.; Lanzatella, N. P.; Venkatraman, L.; Anderson, N. F.; Gullickson, G. C. J. Heterocycl. Chem. 2009, 46, 1154.

Diels-Alder reactions of fused 5-, 6- and 7-membered ring 2-vinylindoles: Synthesis of annulated tetrahydrocarbazoles

Noland, W. E.; Herzig, R. J.; Kumar, H. V.; Narina, V. S.; Elkin, P. K.; Valverde, K. I.; Kim. B. L. Tetrahedron, 2017, 73, 6341-6346.

Crystal structure of 2,3,5,6-tetrabromoterephthalodinitrile

Lastname, F.M.; Lastname, F.M. Journal, year, volume, X–X.

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.

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