Regioselective synthesis of new 5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene bromides and rearrangement reaction thereof
Abstract
(Z)-5-Substituted-2-alkylidene-4-oxothiazolidine derivatives 2a-c were regioselectively brominated to afford the new, synthetically useful vinyl bromides 3a-c, They undergo novel rearrangement reaction to provide 4-oxothiazolidine derivatives 5a-c containing two fully conjugated exocyclic double bonds. Extremely clean and efficient derivatization of 2a-c to 5a-c was also achieved by a one-pot three-step sequence under mild experimental conditions without isolation of vinyl bromides 3a-c.
Keywords:
push-pull alkene / 4-oxothiazolidine derivatives / regioselective bromination / rearrangement reactionSource:
Synlett, 2000, 5, 607-610Publisher:
- Georg Thieme Verlag, Stuttgart
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Marković, R. AU - Baranac-Stojanović, Marija PY - 2000 UR - https://cherry.chem.bg.ac.rs/handle/123456789/434 AB - (Z)-5-Substituted-2-alkylidene-4-oxothiazolidine derivatives 2a-c were regioselectively brominated to afford the new, synthetically useful vinyl bromides 3a-c, They undergo novel rearrangement reaction to provide 4-oxothiazolidine derivatives 5a-c containing two fully conjugated exocyclic double bonds. Extremely clean and efficient derivatization of 2a-c to 5a-c was also achieved by a one-pot three-step sequence under mild experimental conditions without isolation of vinyl bromides 3a-c. PB - Georg Thieme Verlag, Stuttgart T2 - Synlett T1 - Regioselective synthesis of new 5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene bromides and rearrangement reaction thereof IS - 5 SP - 607 EP - 610 UR - https://hdl.handle.net/21.15107/rcub_cherry_434 ER -
@article{ author = "Marković, R. and Baranac-Stojanović, Marija", year = "2000", abstract = "(Z)-5-Substituted-2-alkylidene-4-oxothiazolidine derivatives 2a-c were regioselectively brominated to afford the new, synthetically useful vinyl bromides 3a-c, They undergo novel rearrangement reaction to provide 4-oxothiazolidine derivatives 5a-c containing two fully conjugated exocyclic double bonds. Extremely clean and efficient derivatization of 2a-c to 5a-c was also achieved by a one-pot three-step sequence under mild experimental conditions without isolation of vinyl bromides 3a-c.", publisher = "Georg Thieme Verlag, Stuttgart", journal = "Synlett", title = "Regioselective synthesis of new 5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene bromides and rearrangement reaction thereof", number = "5", pages = "607-610", url = "https://hdl.handle.net/21.15107/rcub_cherry_434" }
Marković, R.,& Baranac-Stojanović, M.. (2000). Regioselective synthesis of new 5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene bromides and rearrangement reaction thereof. in Synlett Georg Thieme Verlag, Stuttgart.(5), 607-610. https://hdl.handle.net/21.15107/rcub_cherry_434
Marković R, Baranac-Stojanović M. Regioselective synthesis of new 5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene bromides and rearrangement reaction thereof. in Synlett. 2000;(5):607-610. https://hdl.handle.net/21.15107/rcub_cherry_434 .
Marković, R., Baranac-Stojanović, Marija, "Regioselective synthesis of new 5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene bromides and rearrangement reaction thereof" in Synlett, no. 5 (2000):607-610, https://hdl.handle.net/21.15107/rcub_cherry_434 .