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Singh, Pardeep
Publications (5 of 5) Show all publications
Singh, P., Adolfsson, D. E., Ådén, J., Cairns, A. G., Bartens, C., Brännström, K., . . . Almqvist, F. (2019). Pyridine-Fused 2-Pyridones via Povarov and A3 Reactions: Rapid Generation of Highly Functionalized Tricyclic Heterocycles Capable of Amyloid Fibril Binding. Journal of Organic Chemistry, 84(7), 3887-3903
Open this publication in new window or tab >>Pyridine-Fused 2-Pyridones via Povarov and A3 Reactions: Rapid Generation of Highly Functionalized Tricyclic Heterocycles Capable of Amyloid Fibril Binding
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2019 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, no 7, p. 3887-3903Article in journal (Refereed) Published
Abstract [en]

We here describe the use of three-component reactions to synthesize tricyclic pyridine ring-fused 2-pyridones. The developed protocols have a wide substrate scope and allow for the installation of diverse chemical functionalities on the tricyclic central fragment. Several of these pyridine-fused rigid polyheterocycles are shown to bind to Aβ and α-synuclein fibrils, which are associated with neurodegenerative diseases.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2019
National Category
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-157464 (URN)10.1021/acs.joc.8b03015 (DOI)000464250800014 ()30862161 (PubMedID)
Funder
Swedish Research Council, 2014-04673Swedish Research Council, 2018-04589Knut and Alice Wallenberg Foundation, KAW 2013.0031The Kempe Foundations, SMK-1755Swedish Foundation for Strategic Research , SB12-0070
Available from: 2019-03-21 Created: 2019-03-21 Last updated: 2019-06-13Bibliographically approved
Singh, P., Cairns, A. G., Adolfsson, D. E., Ådén, J., Sauer, U. H. & Almqvist, F. (2019). Synthesis of Densely Functionalized N-Alkenyl 2-Pyridones via Benzyne-Induced Ring Opening of Thiazolino-Fused 2-Pyridones. Organic Letters
Open this publication in new window or tab >>Synthesis of Densely Functionalized N-Alkenyl 2-Pyridones via Benzyne-Induced Ring Opening of Thiazolino-Fused 2-Pyridones
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2019 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052Article in journal (Refereed) Epub ahead of print
Abstract [en]

We report the synthesis of 6-arylthio-substituted-N-alkenyl 2-pyridones by ring opening of bicyclic thiazolino-2-pyridones with arynes. Varied functionalization was used to investigate scope and substituent influences on reactivity. Selected conditions favor thioether ring opening over [4 + 2] cycloaddition and an unusual aryne incorporating ring expansion. Deuterium labeling was used to clarify observed reactivity. Using the knowledge, we produced drug-like molecules with complex substitution patterns and show how thioether ring opening can be used on scaffolds with competing reactivities.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2019
National Category
Organic Chemistry Inorganic Chemistry Polymer Chemistry
Identifiers
urn:nbn:se:umu:diva-162826 (URN)10.1021/acs.orglett.9b02549 (DOI)31419146 (PubMedID)
Available from: 2019-08-30 Created: 2019-08-30 Last updated: 2019-09-03
Petzold, D., Singh, P., Almqvist, F. & König, B. (2019). Visible light mediated synthesis of β chloro ketones from aryl cyclopropanes. Angewandte Chemie International Edition, 58, 8577-8580
Open this publication in new window or tab >>Visible light mediated synthesis of β chloro ketones from aryl cyclopropanes
2019 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, p. 8577-8580Article in journal (Refereed) Published
Abstract [en]

We report the visible light mediated synthesis of β chloro ketones from aryl cyclopropanes, oxygen, hydrochloric acid and nitric acid. The operationally simple and catalyst free method uses cheap standard lab reagents and displays a broad functional group tolerance. Moreover, scale up of the reaction and late stage functionalization of bioactive compounds is possible, providing the opportunity to utilize the cyclopropane ring as a masked β chloro ketone in a reaction sequence. We propose a light‐driven radical chain reaction initiated by the reaction of diluted hydrochloric and nitric acid producing small quantities of molecular chlorine. The mechanistic hypothesis is supported by 18O labelling and UV‐VIS experiments, cyclovoltammetry and several control reactions.

Place, publisher, year, edition, pages
John Wiley & Sons, 2019
Keywords
photochemistry, aryl cyclopropane, β chloro ketone, radical chain reaction, late-stage modification
National Category
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-157629 (URN)10.1002/anie.201902473 (DOI)000476608700052 ()30901148 (PubMedID)
Available from: 2019-03-26 Created: 2019-03-26 Last updated: 2019-09-09Bibliographically approved
Singh, A., Sharma, B., Sachdeva, D., Mehra, V., Singh, P. & Kumar, V. (2018). β‐Lactam‐Synthon Interceded Diastereoselective Synthesis of 2‐Azido‐γ‐amino Alcohols with Subsequent Transformations to Functionally Enriched Heterocycles. ChemistrySelect, 3(17), 4764-4767
Open this publication in new window or tab >>β‐Lactam‐Synthon Interceded Diastereoselective Synthesis of 2‐Azido‐γ‐amino Alcohols with Subsequent Transformations to Functionally Enriched Heterocycles
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2018 (English)In: ChemistrySelect, ISSN 2365-6549, Vol. 3, no 17, p. 4764-4767Article in journal (Refereed) Published
Abstract [en]

The present manuscript explicates Boron‐dimethylsulfide‐promoted diastereoselective synthesis of 2‐azido‐γ‐amino alcohols using β‐lactam synthon protocol along with its utilization in the formation of diversely functionalized heterocycles having biological relevance. The developed protocol has the potential to surpass the typical drawbacks of conventional protocols.

Place, publisher, year, edition, pages
John Wiley & Sons, 2018
Keywords
2-azido-gamma-amino alcohol, 3-azido-azetidine, cis-oxazinane, intramolecular click chemistry, beta-lactam-synthon protocol
National Category
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-148018 (URN)10.1002/slct.201800512 (DOI)000431625900030 ()
Available from: 2018-05-30 Created: 2018-05-30 Last updated: 2018-06-09Bibliographically approved
Singh, P., Chorell, E., Krishnan, K. S., Kindahl, T., Ådén, J., Wittung-Stafshede, P. & Almqvist, F. (2015). Synthesis of multiring fused 2‑pyridones via a nitrene insertion reaction: fluorescent modulators of α‑synuclein amyloid formation [Letter to the editor]. Organic Letters, 17(24), 6194-6197
Open this publication in new window or tab >>Synthesis of multiring fused 2‑pyridones via a nitrene insertion reaction: fluorescent modulators of α‑synuclein amyloid formation
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2015 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, no 24, p. 6194-6197Article in journal, Letter (Refereed) Published
Abstract [en]

An efficient, straightforward method for the synthesis of thiazolo-2-pyridone embedded peptidomimetic polyheterocycles via a catalyst-free, microwave-assisted, intramolecular C−H amination reaction is reported. All the synthesized polyheterocycles were evaluated for their fluorescent properties and effect on α-synuclein amyloid formation.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2015
National Category
Chemical Sciences
Identifiers
urn:nbn:se:umu:diva-112810 (URN)10.1021/acs.orglett.5b03190 (DOI)000366878300065 ()26650849 (PubMedID)
Available from: 2015-12-15 Created: 2015-12-15 Last updated: 2018-06-07Bibliographically approved
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