Search: onr:"swepub:oai:DiVA.org:umu-189656" >
Tandem Ring Opening...
Tandem Ring Opening/Intramolecular [2 + 2] Cycloaddition Reaction for the Synthesis of Cyclobutane Fused Thiazolino-2-Pyridones
-
- Tyagi, Mohit (author)
- Umeå universitet,Kemiska institutionen
-
- Adolfsson, Dan E., 1989- (author)
- Umeå universitet,Kemiska institutionen
-
- Singh, Pardeep (author)
- Umeå universitet,Kemiska institutionen
-
show more...
-
- Ådén, Jörgen, 1980- (author)
- Umeå universitet,Kemiska institutionen
-
- Jayaweera, Sanduni Wasana (author)
- Umeå universitet,Institutionen för medicinsk kemi och biofysik
-
- Gharibyan, Anna (author)
- Umeå universitet,Institutionen för medicinsk kemi och biofysik
-
- Bharate, Jaideep B. (author)
- Umeå universitet,Kemiska institutionen
-
- Kiss, Anita (author)
- Umeå universitet,Kemiska institutionen
-
- Sarkar, Souvik (author)
- Umeå universitet,Kemiska institutionen
-
- Olofsson, Anders, 1970- (author)
- Umeå universitet,Institutionen för medicinsk kemi och biofysik
-
- Almqvist, Fredrik (author)
- Umeå universitet,Kemiska institutionen
-
show less...
-
(creator_code:org_t)
- 2021-11-12
- 2021
- English.
-
In: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 86:23, s. 16582-16592
- Related links:
-
https://doi.org/10.1...
-
show more...
-
https://umu.diva-por... (primary) (Raw object)
-
https://pubs.acs.org...
-
https://urn.kb.se/re...
-
https://doi.org/10.1...
-
show less...
Abstract
Subject headings
Close
- Reaction of thiazoline fused 2-pyridones with alkyl halides in the presence of cesium carbonate opens the thiazoline ring via S-alkylation and generates N-alkenyl functionalized 2-pyridones. In the reaction with propargyl bromide, the thiazoline ring opens and subsequently closes via a [2 + 2] cycloaddition between an in situ generated allene and the α,β-unsaturated methyl ester. This method enabled the synthesis of a variety of cyclobutane fused thiazolino-2-pyridones, of which a few analogues inhibit amyloid β1–40 fibril formation. Furthermore, other analogues were able to bind mature α-synuclein and amyloid β1−40 fibrils. Several thiazoline fused 2-pyridones with biological activity tolerate this transformation, which in addition provides an exocyclic alkene as a potential handle for tuning bioactivity.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
Find in a library
To the university's database
- By the author/editor
-
Tyagi, Mohit
-
Adolfsson, Dan E ...
-
Singh, Pardeep
-
Ådén, Jörgen, 19 ...
-
Jayaweera, Sandu ...
-
Gharibyan, Anna
-
show more...
-
Bharate, Jaideep ...
-
Kiss, Anita
-
Sarkar, Souvik
-
Olofsson, Anders ...
-
Almqvist, Fredri ...
-
show less...
- About the subject
-
- NATURAL SCIENCES
-
NATURAL SCIENCES
-
and Chemical Science ...
-
and Organic Chemistr ...
- Articles in the publication
-
Journal of Organ ...
- By the university
-
Umeå University