128993-57-7Relevant academic research and scientific papers
Assembly of 1,2,3,4-Tetrahydropyrrolo[1,2- a]pyrazines via the Domino Reaction of 2-Imidazolines and Terminal Electron-Deficient Alkynes
Festa, Alexey A.,Golantsov, Nikita E.,Golubenkova, Alexandra S.,Varlamov, Alexey V.,Voskressensky, Leonid G.
, (2022/02/05)
The transformation of 2-imidazolines into 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines has been realized. A pseudo-three-component reaction of 2-imidazolines with terminal electron-deficient alkynes (2 equiv) first generates imidazolidines, containing an N-vinylpropargylamine fragment. The latter can then undergo a base-catalyzed domino aza-Claisen rearrangement/cyclization reaction sequence, simultaneously constructing pyrrole and pyrazine rings. The process works in a broad substrate scope, delivering pyrrolo[1,2-a]pyrazines in good to excellent yields (45-90%). This two-step approach can be carried out in a one-pot fashion without a noticeable decrease in yield. Remarkably, a three-component protocol for the introduction of two different alkynes has been also developed.
A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes
Festa, Alexey A.,Golantsov, Nikita E.,Golubenkova, Alexandra S.,Varlamov, Alexey V.,Voskressensky, Leonid G.
supporting information, (2020/06/29)
The reaction of 1,2-disubstituted 2-imidazolines with electron-deficient alkynes proceeds as a pseudo-three-component process and forms imidazolidines with an N-vinylpropargylamine fragment. Heating the resulting imidazolidines in xylene on air leads to a
One-pot triflic anhydride-mediated synthesis of 1,2-disubstituted 2-imidazolines from N-(2-haloethyl)amides and amines
Ellsworth, Alyssa A.,Magyar, Christina L.,Hubbell, Grace E.,Theisen, Chelsea C.,Holmes, Daniel,Mosey, R. Adam
, p. 6380 - 6389 (2016/09/23)
A one-pot synthesis of 1,2-disubstituted 2-imidazolines from N-(2-haloethyl)amides has been developed. The reaction affords high yields of diverse 1,2-disubstituted 2-imidazolines from triflic anhydride-mediated dehydration of amides followed by installat
Coenzyme-inspired chemistry 1: The C-2 alkylation of 4,5-dihydroimidazoles
Jones, Raymond C.F.,Nichols, John R.
, p. 4114 - 4119 (2013/06/27)
Alkylation of 4,5-dihydroimidazoles at C-2 is accomplished using a double umpolung of the reactivity of that position, via sulfenylation of a nucleophilic C-2 lithio-species and substitution using an alkyl nucleophile. Arylation via unexpected sulfide con
Palladium-catalyzed multicomponent synthesis of 2-aryl-2-imidazolines from aryl halides and diamines
Geden, Joanna V.,Pancholi, Alpa K.,Shipman, Michael
, p. 4158 - 4164 (2013/05/22)
An efficient palladium-catalyzed three-component reaction that combines aryl halides, isocyanides, and diamines provides access to 2-aryl-2-imidazolines in yields up to 96%. Through variation of the diamine component, the reaction can be extended to the s
One-pot synthesis of imidazolines from aldehydes: detailed study about solvents and substrates
Fujioka, Hiromichi,Murai, Kenichi,Kubo, Ozora,Ohba, Yusuke,Kita, Yasuyuki
, p. 638 - 643 (2007/10/03)
Imidazolines were prepared in one-pot operation from aldehydes and diamines through oxidation of aminal intermediates by NBS. This method could be applied to various aromatic and aliphatic aldehydes and N-nonsubstituted and N-monosubstituted 1,2-diamines. Furthermore, it was found that CH2Cl2 could be altered to TBME, a more environmentally friendly solvent, in the reaction using N-nonsubstituted 1,2-diamines. The reaction conditions were very mild and chemoselective.
New cycloplatinated complexes with 2-arylimidazolines: Synthesis, crystal structures and photophysical properties
Gong, Jun-Fang,Fan, Xin-Heng,Xu, Chen,Li, Jin-Lei,Wu, Yang-Jie,Song, Mao-Ping
, p. 2006 - 2013 (2007/10/03)
The synthesis, crystal structures and photophysical properties of a series of cycloplatinated complexes are presented. The complexes have the general formula (C∧N)Pt(O∧O), where O∧O is acetylacetonate and C∧N re
Tetrahydrofolate coenzyme models: Imidazolines as nucleophilic C1-transfer reagents
Jones,Nichols
, p. 1767 - 1770 (2007/10/02)
1-Benzyl-2-imidazoline is deprotonated at C-2 and alkylated by a sulphenylation-substitution sequence (to complete a formal C1-transfer), whereas arylation occurs by an unusual sulphenylation-sulphide contraction pathway.
