Reaction of organozinc reagents prepared from bromomalonic acid esters and zinc with 3-aryl-2-cyanopropenoic acid primary amides

Shchepin, V. V.; Silaichev, P. S.; Stepanyan, Yu. G.; Russkikh, N. Yu.; Вахрин, М. И.; Ежикова, М. А.; Кодесс, М. И.

doi:10.1134/s1070428006110054

Cited by 4 publications

(2 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cross-sections of the resulting two-dimensional spectrum that are parallel to the F1 axis and passing through signals of the corresponding carbon atoms give one-dimensional spectra displaying only coupling constants with the 3-H proton: 3 J(3-H, C 1′ ) = 4.2, 3 J(3-H, C 3′ ) = 2.9, 3 J(3-H, Me) = 6.1, 3 J(3-H, CO) = 4.6 Hz. Comparison of the vicinal coupling constants for compound XIVa with 3 J CH values found by us previously for substituted cyclopropanes [1,3] led us to conclude that the 3-H proton and the methyl group on C 2 are arranged at the same side of the cyclopropane ring plane. Among two carbonyl carbon atoms in the indandione fragment, the C 1′ atom [downfield signal, δ C 196.87 ppm, 3 J(3-H, C 1′ ) = 4.2 Hz] is oriented cis with respect to 3-H, whereas the C 3′ atom [upfield signal, δ C 194.14 ppm, 3 J(3-H, C 3' ) 2.9 Hz] is oriented trans.…”

mentioning

confidence: 82%

Reactions of bromine-containing organozinc compounds derived from α,α-dibromo ketones with 2-arylmethylideneindan-1,3-diones and 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones

et al. 2010

Self Cite

View full text Add to dashboard Cite

Bromine-containing organozinc compounds generated from 1,1-dibromo-3,3-dimethylbutan-2-one reacted with 2-arylmethylideneindan-1,3-diones and 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones to give 3-aryl-2-(2,2-dimethylpropanoyl)spiro[cyclopropane-1,2′-indan]-1′,3′-diones and 1-aryl-6,6-dimethyl-2-(2,2-dimethylpropanoyl)-5,7-dioxaspiro[2.5]octan-4,8-diones, respectively. Reactions of 2-arylmethylideneindan-1,3-diones with bromine-containing zinc enolates derived from 1-aryl-2,2-dibromopropan-1-ones and 2,2-dibromo-1,2,3,4-tetrahydronaphthalen-1-one resulted in the formation of 2-aroyl-3-aryl-2-methylspiro-[cyclopropane-1,2′-indan]-1′,3′-diones and 2,3 : 8,9-dibenzo-12-phenyldispiro[4.0.5.1]dodecane-1,4,7-trione, respectively.We previously developed a procedure for the synthesis of spirocyclopropanes via reaction of 3-aryl-2-cyanoprop-2-enoic acid derivatives with zinc enolates derived from 2,2-dibromo-1,2,3,4-tetrahydronaphthalen-1-one and 2,2-dibromoindan-1-one [1]. In the present work we made an attempt to find out another synthetic approach to cyclopropane derivatives having one and two spiro carbon atoms. For this purpose, we examined reactions of bromine-containing organozinc compounds derived from α,α-dibromo ketones with 2-arylmethylideneindan-1,3-diones and 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones. In fact, these reactions led to the formation of the corresponding cyclopropanation products as shown in Scheme 1.Zinc enolate II preliminarily generated from 1,1-dibromo-3,3-dimethylbutan-2-one I added at the double C=C bond in substrates IIIa, IIIb, IVa, and IVb to give intermediates Va, Vb, VIIa, and VIIb which underwent cyclization with formation of cyclopropanation products, 1-aryl-6,6-dimethyl-2-(2,2-dimethylpropanoyl)-5,7-dioxaspiro[2.5]octane-4,8-diones VIa and VIb and 3-aryl-2-(2,2-dimethylpropanoyl)spiro[cyclopropane-1,2 ′ -indan]-1′,3′-diones VIIIa and VIIIb (Scheme 1).

show abstract

mentioning

confidence: 82%

Reactions of bromine-containing organozinc compounds derived from α,α-dibromo ketones with 2-arylmethylideneindan-1,3-diones and 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones

et al. 2010

Self Cite

View full text Add to dashboard Cite

show abstract

“…Scheme 25 A one-pot Reformatsky conjugate addition/cyclization sequence from an (E)-benzylidenemalonamide Several variants of the same kind of transformation also emerged between 2005 and 2014, showing that the reaction tolerated variation of both the Reformatsky reagent (formed in situ) and the activated cinnamamide substrate 1c/1c′ (28-71%) (Scheme 26). [81][82][83][84] In most cases, the targeted functionalized 2,6-dioxopiperidines 86 were obtained as a single diastereoisomer in moderate to good yields. It is worth pointing out that these Reformatsky-based reactions complement the deprotonative and enamine versions that were discussed in Section 2.1.…”

Section: Zinc-promoted Transformationsmentioning

confidence: 99%

20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions

Alahyen¹,

Benhamou²,

Dalla³

et al. 2021

Synthesis

View full text Add to dashboard Cite

Acrylamides are versatile building blocks easily obtained from readily available starting materials. During the last 20 years, these valuable substrates bearing a nucleophilic nitrogen atom and an electrophilic double bond have proved to be efficient domino partners leading to a wide variety of complex aza-heterocycles of synthetic relevance. In this non-exhaustive review, metal free and metal triggered reactions followed by an annulation will be presented, these two approaches allowing a good modulation of the reactivity of the polyvalent acrylamides.

show abstract

Reaction of methyl 1-bromocyclopentane-1-carboxylate with zinc and 3-aryl-2-cyanoprop-2-enamides

2014

View full text Add to dashboard Cite

Reaction of organozinc reagents prepared from bromomalonic acid esters and zinc with 3-aryl-2-cyanopropenoic acid primary amides

Cited by 4 publications

References 1 publication

Reactions of bromine-containing organozinc compounds derived from α,α-dibromo ketones with 2-arylmethylideneindan-1,3-diones and 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones

Reactions of bromine-containing organozinc compounds derived from α,α-dibromo ketones with 2-arylmethylideneindan-1,3-diones and 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones

20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions

Reaction of methyl 1-bromocyclopentane-1-carboxylate with zinc and 3-aryl-2-cyanoprop-2-enamides

Contact Info

Product

Resources

About