Sequential bromination-rearrangement of push-pull thiazolidines induced by pyridinium hydrobromide perbromide under homogenous reaction conditions
Abstract
Regiospecific bromination-rearrangement of the 5-substituted 2-alkylidene-4-oxothiazolidine derivatives induced by pyridinium hydrobromide perbromide (PHBP) provides a new synthetic approach to the corresponding push-pull thiazolidines with two exocyclic double bonds. In comparison to a heterogenous alternative, this conversion, taking place in acetonitrile under homogenous reaction conditions, has the advantage of almost quantitative yields and a substantial rate enhancement.
Keywords:
4-oxothiazolidine / enaminic reactivity / elimination / solvent effectSource:
Heterocycles, 2004, 63, 4, 851-860Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
DOI: 10.3987/COM-03-9980
ISSN: 0385-5414
WoS: 000220552200012
Scopus: 2-s2.0-1842419450
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Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Marković, R. AU - Baranac-Stojanović, Marija AU - Džambaski, Z. PY - 2004 UR - https://cherry.chem.bg.ac.rs/handle/123456789/583 AB - Regiospecific bromination-rearrangement of the 5-substituted 2-alkylidene-4-oxothiazolidine derivatives induced by pyridinium hydrobromide perbromide (PHBP) provides a new synthetic approach to the corresponding push-pull thiazolidines with two exocyclic double bonds. In comparison to a heterogenous alternative, this conversion, taking place in acetonitrile under homogenous reaction conditions, has the advantage of almost quantitative yields and a substantial rate enhancement. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Heterocycles T1 - Sequential bromination-rearrangement of push-pull thiazolidines induced by pyridinium hydrobromide perbromide under homogenous reaction conditions VL - 63 IS - 4 SP - 851 EP - 860 DO - 10.3987/COM-03-9980 ER -
@article{ author = "Marković, R. and Baranac-Stojanović, Marija and Džambaski, Z.", year = "2004", abstract = "Regiospecific bromination-rearrangement of the 5-substituted 2-alkylidene-4-oxothiazolidine derivatives induced by pyridinium hydrobromide perbromide (PHBP) provides a new synthetic approach to the corresponding push-pull thiazolidines with two exocyclic double bonds. In comparison to a heterogenous alternative, this conversion, taking place in acetonitrile under homogenous reaction conditions, has the advantage of almost quantitative yields and a substantial rate enhancement.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Heterocycles", title = "Sequential bromination-rearrangement of push-pull thiazolidines induced by pyridinium hydrobromide perbromide under homogenous reaction conditions", volume = "63", number = "4", pages = "851-860", doi = "10.3987/COM-03-9980" }
Marković, R., Baranac-Stojanović, M.,& Džambaski, Z.. (2004). Sequential bromination-rearrangement of push-pull thiazolidines induced by pyridinium hydrobromide perbromide under homogenous reaction conditions. in Heterocycles Pergamon-Elsevier Science Ltd, Oxford., 63(4), 851-860. https://doi.org/10.3987/COM-03-9980
Marković R, Baranac-Stojanović M, Džambaski Z. Sequential bromination-rearrangement of push-pull thiazolidines induced by pyridinium hydrobromide perbromide under homogenous reaction conditions. in Heterocycles. 2004;63(4):851-860. doi:10.3987/COM-03-9980 .
Marković, R., Baranac-Stojanović, Marija, Džambaski, Z., "Sequential bromination-rearrangement of push-pull thiazolidines induced by pyridinium hydrobromide perbromide under homogenous reaction conditions" in Heterocycles, 63, no. 4 (2004):851-860, https://doi.org/10.3987/COM-03-9980 . .