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Synthesis of Arylidenehydrazinyl‐4‐methoxyphenylthiazole Derivatives: Docking Studies, Probing Type II Diabetes Complication Management Agents (2022)
Journal Article
Mehmood, H., Akhtar, T., Haroon, M., Tahir, E., Ehsan, M., Woodward, S., & Musa, M. (2022). Synthesis of Arylidenehydrazinyl‐4‐methoxyphenylthiazole Derivatives: Docking Studies, Probing Type II Diabetes Complication Management Agents. Chemistry and Biodiversity, 19(11), Article e202200824. https://doi.org/10.1002/cbdv.202200824

Thiazole has been a key scaffold in antidiabetic drugs. In quest of new and more effective drugs a simple, efficient, high yielding (67–79 %) and convenient synthesis of arylidenehydrazinyl-4-methoxyphenyl)thiazoles is accomplished over two steps. Th... Read More about Synthesis of Arylidenehydrazinyl‐4‐methoxyphenylthiazole Derivatives: Docking Studies, Probing Type II Diabetes Complication Management Agents.

Rate of Formation of Industrial Lubricant Additive Precursors from Maleic Anhydride and Polyisobutylene (2022)
Journal Article
Streets, J., Proust, N., Parmar, D., Walker, G., Licence, P., & Woodward, S. (2022). Rate of Formation of Industrial Lubricant Additive Precursors from Maleic Anhydride and Polyisobutylene. Organic Process Research and Development, 26(9), 2749-2755. https://doi.org/10.1021/acs.oprd.2c00207

The Alder-ene reaction of neat polyisobutylene (PIB) and maleic anhydride (MAA) to produce the industrially important lubricant additive precursor polyisobutylene succinic anhydride (PIBSA) is studied at 150-180 °C. Under anaerobic conditions with [P... Read More about Rate of Formation of Industrial Lubricant Additive Precursors from Maleic Anhydride and Polyisobutylene.

Identifying Chirality in Line Drawings of Molecules Using Imbalanced Dataset Sampler for a Multilabel Classification Task (2022)
Journal Article
Kok, Y. E., Woodward, S., Özcan, E., & Torres Torres, M. (2022). Identifying Chirality in Line Drawings of Molecules Using Imbalanced Dataset Sampler for a Multilabel Classification Task. Molecular Informatics, 41(12), Article 2200068. https://doi.org/10.1002/minf.202200068

Chirality, the ability of some molecules to exist as two non-superimposable mirror images, profoundly influences both chemistry and biology. Advances in deep learning enable the automatic recognition of chemical structure diagrams, however, studies o... Read More about Identifying Chirality in Line Drawings of Molecules Using Imbalanced Dataset Sampler for a Multilabel Classification Task.

Dewar Benzenoids Discovered in Carbon Nanobelts (2020)
Journal Article
Hanson-Heine, M. W., Rogers, D. M., Woodward, S., & Hirst, J. D. (2020). Dewar Benzenoids Discovered in Carbon Nanobelts. Journal of Physical Chemistry Letters, 11(10), 3769-3772. https://doi.org/10.1021/acs.jpclett.0c01027

© 2020 American Chemical Society. The synthesis of cyclacene nanobelts remains an elusive goal dating back over 60 years. These molecules represent the last unsynthesized building block of carbon nanotubes and may be useful both as seed molecules for... Read More about Dewar Benzenoids Discovered in Carbon Nanobelts.

Conjugate Addition Routes to 2-alkyl-2,3-dihydroquinolin-4(1H)-ones and 2-alkyl-4-hydroxy-1,2-dihydroquinoline-3-carboxylates (2019)
Journal Article
Kingsbury, A., Brough, S., Pedrina McCarthy, A., Lewis, W., & Woodward, S. (2020). Conjugate Addition Routes to 2-alkyl-2,3-dihydroquinolin-4(1H)-ones and 2-alkyl-4-hydroxy-1,2-dihydroquinoline-3-carboxylates. European Journal of Inorganic Chemistry, 2020(11-12), 1011-1017. https://doi.org/10.1002/ejic.201901036

Under CuBr·SMe2/PPh3 catalysis (5/10 mol-%) RMgCl (R = Me, Et, nPr, CH=CH2, nBu, iBu, nC5H11, cC6H11, Bn, CH2Bn, nC11H23) readily (-78 oC) undergo 1,4-addition to Cbz or Boc protected quinolin-4(1H)-ones to provide 2-alkyl-2,3-dihydroquinolin-4(1H)-o... Read More about Conjugate Addition Routes to 2-alkyl-2,3-dihydroquinolin-4(1H)-ones and 2-alkyl-4-hydroxy-1,2-dihydroquinoline-3-carboxylates.

Syntheses of 7-substituted anthra[2,3-b]thiophene derivatives and naphtho[2,3-b:6,7-b’]dithiophene (2018)
Journal Article
Al-jumaili, M. A., & Woodward, S. (2018). Syntheses of 7-substituted anthra[2,3-b]thiophene derivatives and naphtho[2,3-b:6,7-b’]dithiophene. Journal of Organic Chemistry, 83(18), 11437-11445. https://doi.org/10.1021/acs.joc.8b01770

7-R-anthra[2,3-b]thiophene derivatives (1, R = H, Me, i-Pr, MeO) are prepared in three steps (in average overall yield >50%) starting from (E)-4-RC6H4CH2(HOCH2)C=CI(CH2OH). The latter are commercial or readily prepared from 2-butyne-1,4-diol and ArC... Read More about Syntheses of 7-substituted anthra[2,3-b]thiophene derivatives and naphtho[2,3-b:6,7-b’]dithiophene.

Capturing waste heat energy with charge-transfer organic thermoelectrics (2018)
Journal Article
Dimitrov, V., & Woodward, S. (2018). Capturing waste heat energy with charge-transfer organic thermoelectrics. SYNTHESIS, 50(19), 3833-3842. https://doi.org/10.1055/s-0037-1610208

Electrically conducting organic salts, known for over 60 years, have recently demonstrated new abilities to convert waste heat directly into electrical power via the thermoelectric effect. Multiple opportunities are emerging for new structure-propert... Read More about Capturing waste heat energy with charge-transfer organic thermoelectrics.

Synthesis and thermoelectric properties of 2- and 2,8-substituted tetrathiotetracenes (2018)
Journal Article
Robert Garrett, M., Durán-Peña, M. J., Lewis, W., Pudzs, K., Uzulis, J., Mihailovs, I., Tyril, B., Shine, J., Smith, E. F., Rutkis, M., & Woodward, S. (2018). Synthesis and thermoelectric properties of 2- and 2,8-substituted tetrathiotetracenes. Journal of Materials Chemistry C, 6(13), 3403-3409. https://doi.org/10.1039/c8tc00073e

Reaction of elemental sulfur with 2-R1 and 2,8-R1,R2-substituted tetracenes (2) in refluxing DMF affords 5,6,11,12 tetrathiotetracenes (1) in good yields (74-99%) for a range of substituents where R1,R2 are: H,H (a); Me,H (b); MeO,H (c); Ph,H (d); Me... Read More about Synthesis and thermoelectric properties of 2- and 2,8-substituted tetrathiotetracenes.

Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group (2017)
Journal Article
Nouch, R., Cini, M., Magre, M., Abid, M., Diéguez, M., Pàmies, O., Woodward, S., & Lewis, W. (in press). Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group. Chemistry - A European Journal, https://doi.org/10.1002/chem.201704247

Simple enantioselective synthesis of 6,6-disubstituted pentafulvenes bearing chiral pendant hydroxy groups are attained by cascade reactivity using commercially available proline-based organocatalysts. Condensation of cyclopentadiene with the acetyl... Read More about Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group.

Kinetic analysis of Copper(I)/Feringa-Phosphoramidite Catalysed AlEt3 1,4-Addition to Cyclohex-2-en-1-one (2017)
Journal Article
Willcox, D., Nouch, R., Kingsbury, A., Robinson, D., Carey, J. V., Brough, S., & Woodward, S. (in press). Kinetic analysis of Copper(I)/Feringa-Phosphoramidite Catalysed AlEt3 1,4-Addition to Cyclohex-2-en-1-one. ACS Catalysis, https://doi.org/10.1021/acscatal.7b02198

ReactIR studies of mixtures of AlEt3 (A) and cyclohex-2-en-1-one (CX) in Et2O indicate immediate formation of the Lewis acid-base complex (CX.A) at -40 oC (K = 12.0 M-1, ΔGoreact -1.1 kcal mol-1). Copper(I) catalysts, derived from pre-catalytic Cu(OA... Read More about Kinetic analysis of Copper(I)/Feringa-Phosphoramidite Catalysed AlEt3 1,4-Addition to Cyclohex-2-en-1-one.