55690-01-2Relevant articles and documents
Synthesis and study of Au(iii)-indolizine derivatives: Turn-on luminescence by photo-induced controlled release
Yang, Jie,Zhu, Yifan,Tse, Anfernee Kai-Wing,Zhou, Xinghua,Chen, Yang,Tse, Yu Chung,Wong, Keith Man-Chung,Ho, Chun-Yu
, p. 4471 - 4474 (2019)
The photo- and structural properties of a series of Au(iii) indolizine complexes were determined. Controlled release of halogenated indolizine derivatives from the corresponding Au(iii) complexes was achieved by photoinduced C-X bond formation, which provided turn-on luminescence with an increase in emission intensity of up to 67 times.
Straightforward Access to 2-Iodoindolizines via Iodine-Mediated Cyclization of 2-Pyridylallenes
Alahyen, Ismail,Fensterbank, Louis,Lemière, Gilles,Martinez, Thibaut,Mouriès-Mansuy, Virginie
supporting information, p. 817 - 821 (2020/07/14)
A metal-free access to 2-iodo-1,3-disubstituted indolizines has been developed. The proposed synthesis is relatively simple and efficient and involves the iodine-triggered 5-endo-trig cyclization of 2-pyridylallene precursors. While it can be conducted on
Synthesis of new cyclazines and 4,5-diaryl-1 H -pyrrol-3(2 H)-one units in discoipyrroles from indolizinone-DMAD cycloadducts
Kurian, Jais,Kannoth M, Muraleedharan
supporting information, p. 8832 - 8848 (2019/10/22)
The reaction of indolizinones with dimethyl acetylenedicarboxylate gave direct access to 3′,8a-dihydrocyclopenta[hi]indolizin-8a-ol and 1H-pyrrol-3(2H)-one in good yields. The former skeleton is a precursor to cyclazines with nitrogen on the periphery, a hitherto un-accessed 10-π system. Their formation involves initial [4 + 2] or [8 + 2] modes of cycloadditions; the retro-Diels Alder reaction of the [4 + 2] cycloadduct leads to 1H-pyrrol-3(2H)-one, whereas [8 + 2] addition followed by π-reorganization leads to the azatricyle. Analysis of substituent effects on product distribution showed that electron donating groups on the C3-aryl ring promote the formation of the azatricycle preponderantly. Treatment of one of these azatricycles (3c) with HBF4 led to the formation of the corresponding 10e-aromatic species which was detected by NMR spectroscopy. In addition, formation of the 1H-pyrrol-3(2H)-one skeleton through the normal retro-Diels Alder pathway was employed in the total synthesis of Discoipyrrole C, which is a new lead against lung cancer.
Efficient solvent-free synthesis of tertiary propargylic alcohols from arylacetylenes and ketones promoted by tert-BuOK
Chen, Shufeng,Yuan, Fang,Zhao, Haiying,Li, Baoguo
, p. 2391 - 2399 (2013/07/26)
A mild and efficient method for the alkynylation of arylacetylenes with ketones promoted by tert-BuOK under solvent-free conditions was developed. The present green synthesis was applicable to many kinds of aromatic and aliphatic ketones providing good to excellent yields of tertiary propargylic alcohols. Graphical abstract: A mild and efficient method for the alkynylation of arylacetylenes with ketones promoted by tert-BuOK under solvent-free conditions was developed. The present green synthesis was applicable to many kinds of aromatic and aliphatic ketones providing good to excellent yields of tertiary propargylic alcohols.[Figure not available: see fulltext.]
Palladium-catalyzed construction of poly-substituted indolizinones
Cho, Hanyang,Kim, Ikyon
experimental part, p. 5464 - 5480 (2012/09/08)
We have developed a highly efficient one-pot approach to poly-substituted indolizinones from tertiary propargylic alcohols by using a palladium-catalyzed domino reaction. This reaction is proposed to proceed via successive aminopalladation, reductive elim
Indolizinones as synthetic scaffolds: Fundamental reactivity and the relay of stereochemical information
Hardin Narayan, Alison R.,Sarpong, Richmond
supporting information; experimental part, p. 70 - 78 (2012/01/04)
Indolizinones are under-explored N-heterocycles that react with exquisite chemo- and stereoselectivity. An exploration of the fundamental reactivity of these azabicycles demonstrates the potential to relay stereochemical information from the ring-fusion to newly formed stereocenters on the bicyclic core. The indolizinone diene undergoes selective hydrogenation and readily participates in Diels-Alder cycloadditions as well as ene reactions. The vinylogous amide embedded in the five-membered ring is resistant to reaction when the diene is in place. However, removal of the diene allows for diastereoselective hydrogenation of, and 1,4-additions to, the vinylogous amide. These fundamental reactions with indolizinones have provided a structurally diverse array of products that hold promise in the context of natural product synthesis.
