β,β-Dinitrostyrenes in reactions with cyclohexane-1,3-diones

Trukhin, E. V.; Sheremet, E. A.; Berestovitskaya, V. M.

doi:10.1007/s11172-009-0278-x

Cited by 7 publications

(1 citation statement)

References 5 publications

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“…In this context, in 2004 and 2009, Trukhin and coworkers investigated the reaction of bromonitroalkenes with acetylacetone and 1,3-cyclohexanedione in the presence of a base such as Et 3 N or sodium methoxide to prepare the corresponding 2,3-dihydrofurans and their fused derivatives in racemic form ( rac - 13 ) (Scheme 5). 11…”

Section: Reaction With Active Methylene Compoundsmentioning

confidence: 99%

Bromonitroalkenes as efficient intermediates in organic synthesis

Ziyaei Halimehjani,

Tahvildari

2024

Org. Biomol. Chem.

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Section: Reaction With Active Methylene Compoundsmentioning

confidence: 99%

Bromonitroalkenes as efficient intermediates in organic synthesis

Ziyaei Halimehjani,

Tahvildari

2024

Org. Biomol. Chem.

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Synthesis of β-(trifluoromethyl)furans and spiro-gem-dichlorocyclopropanes from cyclic 1,3-dicarbonyl compounds and α-(trihaloethylidene)nitroethanes

Barkov

Korotaev

Sosnovskikh

2013

Tetrahedron Letters

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a b s t r a c t While 1,3-dicarbonyl compounds react with (E)-1,1,1-trifluoro-3-nitrobut-2-ene in the presence of sodium acetate to produce the target b-(trifluoromethyl)furans, their reaction with (E)-1,1,1-trichloro-3-nitrobut-2-ene, under the same conditions, took an entirely different course and gave spiro-gemdichlorocyclopropanes bearing a 1-nitroethyl moiety, with high diastereoselectivity and in good yields.Ó 2013 Elsevier Ltd. All rights reserved.Conjugated nitroolefins are widely used in organic synthesis due to the high electrophilicity of the double bond.1 As a result, partially fluorinated nitroalkenes have attracted attention as excellent building blocks for the preparation of various R F -containing compounds.2 In particular, polyfluoroalkylated nitroalkenes react with enamines of cycloalkanones and methyl ketones to give b-polyfluoroalkyl-c-nitroketones, 3 nitro alkylated enamines, and 1,2-oxazine N-oxides, 4 as well as 1-pyrroline N-oxides. 5 At the same time, very little information is available on the reactions of trihalomethylated conjugated nitroalkenes with 1,3-dicarbonyl compounds. Only one Letter is known reporting the reaction of 3,3,3-trifluoro-1-nitropropene with 1,3-dicarbonyl compounds to give the corresponding addition products. 6 Recently, we reported that 1,1,1-trifluoro-3-nitrobut-2-ene (1a) reacted with 1,3-diketones and primary aliphatic amines to give substituted b-(trifluoromethyl)pyrroles via the Grob cyclization. On the other hand, it is well-known that b-diketones and b-ketoesters add to nitroalkenes to form substituted dihydrofurans or furans depending on the number and nature of the substituents at the nitroalkene double bond. 8 In this furan synthesis, nitroalkenes are commonly employed because the nitro group can act as both a powerful stabilizer of the intermediate anion and as a good leaving group in the aromatization forming a furan ring. In the case of 1,1,1-trifluoro-3-nitrobut-2-ene (1a) and 1,1,1-trichloro-3-nitrobut-2-ene (1b), it would be reasonable to assume the possibility of an intramolecular Nef reaction occurring with formation of the b-(trihalomethyl)furan core. In this context, and in connection with our interest in the development of CX 3 -nitroolefin (X = F, Cl) chemistry, 4,5,7 a method for the preparation of the b-(trihalomethyl)furan system based on the Nef reaction, in a one-pot procedure, attracted our attention. The present communication describes the dramatic effect of the trihalomethyl group on the pathway of the reactions between a-(trihaloethylidene)nitroethanes 1a,b and 1,3-dicarbonyl compounds. Although a number of methods have been developed for the construction of b-(trifluoromethyl)furans, 9 which are versatile intermediates in synthetic organic chemistry, 10 their simple and convenient synthesis still remains an attractive goal. Furthermore, benzofuran derivatives bearing a trifluoromethyl group at the 3-position have, surprisingly, been poorly investigated, probably due to the few methods available for their preparation. 11We found th...

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