Investigation of reactions of the organozinc reagents prepared from zinc and dialkyl dibromomalonates with the derivatives of 2-arylmethyleneindan-1,3-dione and 5-arylmethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

Shchepin, V. V.; Stepanyan, Yu. G.; Silaichev, P. S.

doi:10.1134/s1070363208050162

Cited by 8 publications

(3 citation statements)

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“…( S )‐Dimethyl 1′,3′‐Dioxo‐3‐phenyl‐1′,3′‐dihydrospiro(cyclopropane‐1,2′‐indene)‐2,2‐dicarboxylate (3a): 17b [ α ] D 27 = –58.7 ( c = 0.4, CHCl 3 ), ee 67 %. HPLC analysis with Chiralpak column AD‐H, n ‐hexane/2‐propanol (90:10), 1.0 mL min −1 , detection at 254 nm; minor enantiomer t R = 17.9 min, major enantiomer t R = 22.1 min.…”

Section: Methodsmentioning

confidence: 99%

Cyclohexane Ring as a Tool to Select the Presentation of the Carbohydrate Moiety in Glycosyl Amino Acids

Rodrı́guez

Somovilla

Corzana

et al. 2012

Chemistry A European J

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The design of mimic molecules that resemble natural products can be a useful tool to help understand the key aspects in molecular recognition processes that are difficult to access by using natural derivatives. We present the synthesis and the conformational analysis of different glucosylated diamide amino acids that simulate glycopeptides with β-O-linked glucose and contain the nonnatural β-hydroxycyclohexane-α-amino acid. The study, using NMR experiments, X-ray spectroscopy, and molecular dynamics simulations, reveals that the cyclohexane ring allows some naturally occurring ways of presentation of the carbohydrate to be fixed, or to stabilize some novel conformations. In addition, different chair conformations for the cyclohexane-α-amino acid moiety can be set, in particular, those with high population of conformers in which the bulky groups are located at axial positions. Moreover, to increase the scope of these cyclohexane derivatives, two dipeptides incorporating the glycomimics have been synthesized and further glycosylated to obtain the corresponding α-O-glycopeptides. These features can have important implications for the design of new drugs and for understanding the complex molecular processes that take place between glycopeptides and their biological targets.

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Section: Methodsmentioning

confidence: 99%

Cyclohexane Ring as a Tool to Select the Presentation of the Carbohydrate Moiety in Glycosyl Amino Acids

Rodrı́guez

Somovilla

Corzana

et al. 2012

Chemistry A European J

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“…[17][18][19][20][21][22][23][24][25] Some methods have been developed for the synthesis of spirocyclopropanes from indane-1,3-diones by the MIRC strategy involving the oxidative addition of various aldehydes with indane-1,3-dione in the presence of iodine and DMAP under mechanical milling conditions, 26 the reaction of 2-arylideneindane-1,3-diones and 2-arylidenemalononitriles with different α-monohalogenated methylene active compounds using trimethylamine, or the reaction of 2-arylideneindane-1,3-diones with dimethyl bromomalonate in the presence of α,α-L-diarylprolinol and K 2 CO 3 , 27 and the reaction of dialkyl dibromomalonates with 2-arylmethyleneindane-1,3-dione in the presence of zinc in THF. 28 Since halo-organic compounds are widely used in organic synthesis and in the chemistry of natural compounds, many attempts have been made to develop new methods and reagents for selective halogenation. The use of some halogenating agents requires special equipment and techniques because of their explosive, toxic, unstable, and hygroscopic qualities.…”

Section: Syn Thesismentioning

confidence: 99%

Synthesis of Activated Cyclopropanes by MHIRC Strategy: A Facile and Efficient Approach to Spirocyclopropanes Using N-Halosulfonamides

Ghorbani‐Vaghei

Maghbooli

2016

Synthesis

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In this study, a one-pot, three-component reaction of two molecules of indane-1,3-dione with aromatic aldehydes for the synthesis of spirocyclopropylindanediones using poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) (PBBS), N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide (TBBDA), poly(N-chloro-N-ethylbenzene-1,3-disulfonamide) (PCBS), and N,N,N′,N′-tetrachlorobenzene-1,3-disulfonamide (TCBDA) as novel reagents has been developed. In addition, an effective and simple domino procedure for the preparation of spirodicyanocyclopropylindanediones from indane-1,3-dione and 2-arylidenemalononitriles is reported. These reactions involve Michael addition, halogenation, and intramolecular ring-closing (MHIRC) reaction sequences.The smallest cycloalkane is found as a main structural element in a broad range of naturally occurring compounds. 1 Cyclopropanes are attractive and often sought synthetic targets, because the specific reactivity of this carbocyclic ring system renders them useful as versatile intermediates in the synthesis of complex molecules. 2 The spiro ring effectively restricts the aromatic ring to different conformations without a large increase in carbon number or strict bulk. Restriction of aromatic rings to different areas relative to the spiro ring may produce compounds with different pharmacological activity. 3,4 Therefore, the construction of spiro-cyclopropane skeletons has attracted extensive attention, and a variety of efficient procedures have been developed for the synthesis of these important structures, including Michael-initiated ring closure (MIRC), transition-metal-catalyzed carbine transfer, organocatalytic cyclopropanation, and from alkenes by Simmons-Smith and related reactions or with ylides, for example, phosphorus, sulfur, arsenic, and phenyliodonium ylides. [5][6][7][8][9][10][11][12] One of the most common methods for the construction of cyclopropane rings is Michael-initiated ring closure (MIRC) from electron-poor alkenes. 13 According to the nature of the involved substrates/reactants, we can divide these reactions into two classes. 14 The first one includes Michael addition of a substrate bearing a leaving group to an activated alkene. The second type of MIRC method involves nucleophilic addition to electrophilic substrates that contain a leaving group for the formation of cyclopropanes. 15 In the Michael addition-halogenation-intramolecular ring-closing (MHIRC) strategy, the halogen atom as a leaving group can attach to substrates or reactants during the reaction, which then undergoes intramolecular ring closure to produce the corresponding three-membered ring (Scheme 1). 16

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“…2-Arylidene-1,3-indandiones are mostly attractive Michael acceptors [1][2][3][4][5] for the resulted substituted 1,3-indandiones had been widely found in many natural products with useful biological activities (Scheme 1). [6][7][8][9][10][11] Among various 1,3-indandiones and their derivatives, multicyclic spiro-1,3-indandiones are especially valuable.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of activated spirocyclopentanes via a cascade Michael/alkylation reaction of ethyl-4-chloro-3-oxobutanoate and 2-arylidene-1,3-indandiones

Luo¹,

Zheng²,

Zhang³

et al. 2015

Arkivoc

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Investigation of reactions of the organozinc reagents prepared from zinc and dialkyl dibromomalonates with the derivatives of 2-arylmethyleneindan-1,3-dione and 5-arylmethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

Cited by 8 publications

References 0 publications

Cyclohexane Ring as a Tool to Select the Presentation of the Carbohydrate Moiety in Glycosyl Amino Acids

Cyclohexane Ring as a Tool to Select the Presentation of the Carbohydrate Moiety in Glycosyl Amino Acids

Synthesis of Activated Cyclopropanes by MHIRC Strategy: A Facile and Efficient Approach to Spirocyclopropanes Using N-Halosulfonamides

Synthesis of activated spirocyclopentanes via a cascade Michael/alkylation reaction of ethyl-4-chloro-3-oxobutanoate and 2-arylidene-1,3-indandiones

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Investigation of reactions of the organozinc reagents prepared from zinc and dialkyl dibromomalonates with the derivatives of 2-arylmethyleneindan-1,3-dione and 5-arylmethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

Cited by 8 publications

References 0 publications

Cyclohexane Ring as a Tool to Select the Presentation of the Carbohydrate Moiety in Glycosyl Amino Acids

Cyclohexane Ring as a Tool to Select the Presentation of the Carbohydrate Moiety in Glycosyl Amino Acids

Synthesis of Activated Cyclopropanes by MHIRC Strategy: A Facile and Efficient Approach to Spirocyclopropanes Using N-Halosulfon­amides

Synthesis of activated spirocyclopentanes via a cascade Michael/alkylation reaction of ethyl-4-chloro-3-oxobutanoate and 2-arylidene-1,3-indandiones

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Synthesis of Activated Cyclopropanes by MHIRC Strategy: A Facile and Efficient Approach to Spirocyclopropanes Using N-Halosulfonamides