A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach [PDF]
Beilstein Journal of Organic Chemistry, 2021 The reported flow-batch approach enables the easy preparation of 2H-azirines and their stereoselective transformation into highly functionalized NH-aziridines, starting from vinyl azides and organolithium compounds.
Michael Andresini +2 more
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Copper(I)-catalyzed asymmetric decarboxylative Mannich reaction enabled by acidic activation of 2H-azirines [PDF]
Nature Communications, 2019 Due to their poor electrophilicity, 2H-azirines do not easily react with nucleophiles. Here, the authors show an acidic activation of 2H-azirines by cyanoacetic acid coupling partners affording chiral aziridines containing vicinal tetrasubstituted and ...
Hai-Jun Zhang, Yan-Cheng Xie, Liang Yin
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Azirinium ylides from α-diazoketones and 2H-azirines on the route to 2H-1,4-oxazines: three-membered ring opening vs 1,5-cyclization [PDF]
Beilstein Journal of Organic Chemistry, 2015 Strained azirinium ylides derived from 2H-azirines and α-diazoketones under Rh(II)-catalysis can undergo either irreversible ring opening across the N–C2 bond to 2-azabuta-1,3-dienes that further cyclize to 2H-1,4-oxazines or reversibly undergo a 1,5 ...
Nikolai V. Rostovskii +4 more
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Synthesis of New 2-Halo-2-(1H-tetrazol-5-yl)-2H-azirines via a Non-Classical Wittig Reaction [PDF]
Molecules, 2015 The synthesis and reactivity of tetrazol-5-yl-phosphorus ylides towards N-halosuccinimide/TMSN3 reagent systems was explored, opening the way to new haloazidoalkenes bearing a tetrazol-5-yl substituent.
Ana L. Cardoso +4 more
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Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems [PDF]
Beilstein Journal of Organic Chemistry, 2014 3-Aryl-2H-azirines react with acylketenes, generated by thermolysis of 5-arylfuran-2,3-diones, to give bridged 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene-2,10-diones and/or ortho-fused 6,6a,12,12a-tetrahydrobis[1,3]oxazino[3,2-a:3′,2′-d]pyrazine-4,10 ...
Alexander F. Khlebnikov +4 more
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Addition and Cycloaddition Reactions of Phosphinyl- and Phosphonyl-2H-Azirines, Nitrosoalkenes and Azoalkenes [PDF]
Molecules, 2009 An overview of the use of 2H-azirines, conjugated nitrosoalkenes and conjugated azoalkenes bearing phosphorus substituents in addition and cycloaddition reactions is presented, focused on strategies for the synthesis of aminophosphonate and ...
Américo Lemos
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Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination [PDF]
Beilstein Journal of Organic Chemistry, 2018 The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO ...
Jiyun Sun +5 more
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3-Aryl-2H-azirines as annulation reagents in the Ni(II)-catalyzed synthesis of 1H-benzo[4,5]thieno[3,2-b]pyrroles [PDF]
Beilstein Journal of Organic ChemistryA high-yielding method for the synthesis of 3-arylbenzo[4,5]thieno[3,2-b]pyrroles has been developed via pyrrole ring annulation to the aromatic benzo[b]thiophene system, using 3-arylazirines as a N‒C=C synthon.
Julia I. Pavlenko +5 more
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Synthesis of 2-halo-2H-azirines [PDF]
Tetrahedron, 2001 Abstract α-Oxophosphonium ylides react with N -chlorosuccinimide, N -bromosuccinimide and N -iodosuccinimide in the presence of azidotrimethylsilane giving the corresponding haloazidoalkenes which were completely converted to the 2-halo-2 H -azirines on heating in heptane.
Ana L Cardoso
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Light-induced synthesis of 2H-azirines and its applications in organic chemistry
Journal of Saudi Chemical Society2H-azirines have represented versatile building motifs in the domain of organic chemistry owing to their excellent reaction activity induced by the high strain of the three-membered ring species.
Yiwen Chu, Junfeng Deng
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