New atropoisomeric alkenylphenylglycine derivatives: Synthesis of (5R*)- and (5S*)-isomers of (1R*,3aR*,4S*,11S*)-3a,5,9,11-tetramethyl-4,5-dihydro-3aH-1,4-methano[1,3]oxazolo[3,2-a]quinolin-2-one

Bizhanova, Guliya G.; Suponitsky, Kyrill Yu.; Vakhitova, Yu. V.; Гатауллин, Р. Р.

doi:10.1016/j.tet.2016.11.038

Cited by 8 publications

(2 citation statements)

References 64 publications

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“…They can undergo 1,3‐dipolar cycloaddition (13DC) reactions with alkenes and alkynes, forming bicyclic products that can be easily transformed into pyrroles by CO 2 loss . This bears a great practical importance, since it provides a very attractive synthetic route to pyrrole derivatives, a motif often found in medical drugs, and as intermediates in different synthetic routes . Therefore, it is not strange that a large number of experimental and theoretical reports have been devoted to study this family of reactions, with special emphasis on the elucidation of the factors that govern the formation of a given regio‐isomer …”

Section: Introductionmentioning

confidence: 99%

Geometrical distortions and charge transfer in munchnöne regio‐selectivity: A conceptual density functional study

González

Hernández‐Castillo

Montero‐Cabrera

et al. 2017

Int J of Quantum Chemistry

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Dipolar cycloaddition reactions involving munchnönes and simple dipolarophiles provide a versatile synthetic route toward pyrrole derivatives. However, despite their widespread use, there are still debates regarding the factors governing the regio‐selectivity of these reactions. In this contribution, we study the regio‐selectivity of 1,3‐dipolar cycloadditions of munchnönes and alkenes, and the ability of conceptual density functional theory (c‐DFT) descriptors to correctly study these processes. We base our analysis on the variation of different reactivity descriptors along the reaction path, calculated for the whole reacting complex, and for the isolated species, with the strained geometries they present within this supra‐molecular aggregate. The study of several global descriptors indicates that the path leading to the preferred product proceeds via an asynchronous mechanism, with the maximum extent of charge transfer occurring after the transition state. This helps to understand why several reactivity principles fail to correctly account for the position of the transition state in this case. This also explains why local c‐DFT descriptors fail to predict the observed majoritarian regio‐isomer. These results highlight the fundamental role of the distortion effects for determining the extent of charge transfer between the reactants, and thus their impact on the reactivity and regio‐selectivity in these reactions.

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Section: Introductionmentioning

confidence: 99%

Geometrical distortions and charge transfer in munchnöne regio‐selectivity: A conceptual density functional study

González

Hernández‐Castillo

Montero‐Cabrera

et al. 2017

Int J of Quantum Chemistry

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“…Both the ester 1 and acid 5 exist as a mixture of synand anti-atropisomeric compounds. 16,20 Depending on the synthetic method employed, different ratios of the ester 1 isomers can be obtained. The isomer ratio was determined by integration of the proton signals in the 1 H NMR spectrum.…”

Section: Syn Thesismentioning

confidence: 99%

An Unexpected Dihalogenation/Dehydrogenation Product Derived via Iodolactonization of an N-Tosyl-N-[6-(2-cyclopenten-1-yl)-2-methylphenyl]glycine

et al. 2019

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The reaction between N-tosyl-N-[6-(2-cyclopenten-1-yl)phenyl]glycine (syn/anti atropisomeric mixture) and molecular iodine is studied. Along with the expected 8-exo-cyclization product possessing a 3-iodo-2,3,3a,6,7,11b-hexahydrobenzo[e]cyclopenta[g][1,4]oxazocine core, the unexpected 1,11b-dehydrogenated/1-iodinated analogue with a 1,3-diiodo-3,3a,6,7-tetrahydrobenzo[e]cyclopenta[g][1,4]oxazocine structure is observed for the first time in a conventional halolactonization reaction.

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Synthesis of (1′S,2R,3R)‐ and (1′S,2R,3S)‐N‐arylsulfonyl‐2‐(1′‐halogenethyl)‐3‐methylindolines and their selective toxicity against SH‐SY5Y cell line

Гатауллин

Zileeva

Maksimova

et al. 2020

Journal of Heterocyclic Chem

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N‐tosyl‐2‐ and N‐tosyl‐4‐halogen‐substituted derivatives of 2‐(1‐methylbut‐2‐en‐1‐yl)aniline were synthesized and their molecular iodine‐mediated cyclization was investigated. The cyclization upon interaction of N‐tosyl‐6‐methyl‐2‐(1‐methylbut‐2‐en‐1‐yl)aniline with molecular iodine in methyl tert‐butyl ether or acetonitrile was studied, as well as the interaction of this sulfonamide with N‐bromosucinimide in dichloromethane. Synthesized (2R*,3R*)‐ and (2R*,3S*)‐N‐arylsulfonyl‐2‐(1‐halogenoethyl)‐3‐methylindoline derivatives showed cytotoxic activity against HEK293 cells, SH‐SY5Y, Jurkat, and HepG2 cell lines. The compounds (2R*,3S*)‐N‐arylsulfonyl‐7‐bromo‐2‐(1‐halogenoethyl)‐3‐methylindoline cis‐4a, stereoisomeric (2R*,3R*)‐trans‐4h and (2R*,3S*)‐N‐tosyl‐7‐chloro‐2‐(1‐halogenoethyl)‐3‐methylindoline cis‐4h demonstrated selective toxicity against SH‐SY5Y cell line (IC50 ≈ 3 ÷ 5 μM), and did not affect HEK293, Jurkat, and HepG2 cells.

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New atropoisomeric alkenylphenylglycine derivatives: Synthesis of (5R)- and (5S)-isomers of (1R,3aR,4S,11S)-3a,5,9,11-tetramethyl-4,5-dihydro-3aH-1,4-methano[1,3]oxazolo[3,2-a]quinolin-2-one

Cited by 8 publications

References 64 publications

Geometrical distortions and charge transfer in munchnöne regio‐selectivity: A conceptual density functional study

Geometrical distortions and charge transfer in munchnöne regio‐selectivity: A conceptual density functional study

An Unexpected Dihalogenation/Dehydrogenation Product Derived via Iodolactonization of an N-Tosyl-N-[6-(2-cyclopenten-1-yl)-2-methylphenyl]glycine

Synthesis of (1′S,2R,3R)‐ and (1′S,2R,3S)‐N‐arylsulfonyl‐2‐(1′‐halogenethyl)‐3‐methylindolines and their selective toxicity against SH‐SY5Y cell line

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New atropoisomeric alkenylphenylglycine derivatives: Synthesis of (5R*)- and (5S*)-isomers of (1R*,3aR*,4S*,11S*)-3a,5,9,11-tetramethyl-4,5-dihydro-3aH-1,4-methano[1,3]oxazolo[3,2-a]quinolin-2-one

Cited by 8 publications

References 64 publications

Geometrical distortions and charge transfer in munchnöne regio‐selectivity: A conceptual density functional study

Geometrical distortions and charge transfer in munchnöne regio‐selectivity: A conceptual density functional study

An Unexpected Dihalogenation/Dehydrogenation Product Derived­ via Iodolactonization of an N-Tosyl-N-[6-(2-cyclopenten-1-yl)-2-methylphenyl]glycine

Synthesis of (1′S*,2R*,3R*)‐ and (1′S*,2R*,3S*)‐N‐arylsulfonyl‐2‐(1′‐halogenethyl)‐3‐methylindolines and their selective toxicity against SH‐SY5Y cell line

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New atropoisomeric alkenylphenylglycine derivatives: Synthesis of (5R)- and (5S)-isomers of (1R,3aR,4S,11S)-3a,5,9,11-tetramethyl-4,5-dihydro-3aH-1,4-methano[1,3]oxazolo[3,2-a]quinolin-2-one

An Unexpected Dihalogenation/Dehydrogenation Product Derived via Iodolactonization of an N-Tosyl-N-[6-(2-cyclopenten-1-yl)-2-methylphenyl]glycine

Synthesis of (1′S,2R,3R)‐ and (1′S,2R,3S)‐N‐arylsulfonyl‐2‐(1′‐halogenethyl)‐3‐methylindolines and their selective toxicity against SH‐SY5Y cell line