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

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.

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 structures of 2,4,6-tri-iodo-benzo-nitrile and 2,4,6-tri-iodo-phenyl isocyanide.

Noland WE, Britton D, Sutton GK, Schneerer AK, Tritch KJ Acta Crystallogr E Crystallogr Commun. 2018, 9;74(Pt 2):98-102.

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.

3,5-Dibromobenzonitrile

Wayland E. Noland and Kenneth J. Tritch. 3,5-Dibromobenzonitrile, IUCrData, 2018, 3, x180059

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.

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