Reaction of 1-Azabicyclo[1.1.0]butane with Activated Amides

Hayashi, Kazuhiko; Kujime, Eiko; Katayama, Hajime; Sano, Shigeki; Nagao, Yoshimitsu

doi:10.3987/com-09-11677

Cited by 9 publications

(4 citation statements)

References 26 publications

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“…6,[8][9][10][11][12][13] We have already established an efficient method for cyclization to highly strained bicyclic molecules with a lithium cation. [14][15][16][17][18][19][20][21][22] Those results prompted us to clarify the action of LiOH in a water/THF solution. We discuss herein the role of LiOH in hydrolysis by comparing the differences in yields between various hydroxides (KOH, NaOH, LiOH) used for the hydrolysis of benzoates and aliphatic esters.…”

Section: Introductionmentioning

confidence: 99%

Efficiency of Lithium Cations in Hydrolysis Reactions of Esters in Aqueous Tetrahydrofuran

et al. 2021

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Lithium cations were observed to accelerate the hydrolysis of esters with hydroxides (KOH, NaOH, LiOH) in a water/tetrahydrofuran (THF) two-phase system. Yields in the hydrolysis of substituted benzoates and aliphatic esters using the various hydroxides were compared, and the effects of the addition of lithium salt were examined. Moreover, it was presumed that a certain amount of LiOH was dissolved in THF by the coordination of THF with lithium cation and hydrolyzed esters even in the THF layer, as in the reaction by a phase-transfer catalyst.

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Section: Introductionmentioning

confidence: 99%

Efficiency of Lithium Cations in Hydrolysis Reactions of Esters in Aqueous Tetrahydrofuran

et al. 2021

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“…The title compound was synthesized by reacting 1-azabicyclo-[1.1.0] butane and 3-benzoyl-1,3-thiazolidine-2-thione in the presence of a Lewis acid, such as Mg(OTf )2. 4 Then, the crude compound was purified using column chromatography, followed by recrystallization from diethyl ether.…”

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confidence: 99%

Crystal Structure of 2-(1-Benzoylazetidin-3-yl)thio-1,3-thiazoline

Sugiura

Ichimaru

Kato

et al. 2021

X-ray Structure Analysis Online

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“…1,2 In some of our recent papers, reactions of 1 with diverse electrophiles, such as sulfanyl and sulfinyl chlorides 3 as well as chlorodithioformates, 4 were described. In analogy to other reactions of 1 with electrophilic agents, e.g.…”

Section: Introductionmentioning

confidence: 99%

Three-Component Reactions with 3-Phenyl-1-azabicyclo[1.1.0]butane, Dimethyl Dicyanofumarate, and Primary Aromatic Amines

Mlostoń¹,

Heimgartner²

2010

HETEROCYCLES

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The three-component reaction of 3-phenyl-1-azabicyclo[1.1.0]butane (1a) with 2,3-dicyanofumarates (DCFM) and primary aromatic amines in dichloromethane at room temperature yielded mixtures of (Z)-2-arylamino-3-cyanofumarates (7) and the corresponding (E)-2-(azetidin-1-yl)-3-cyanomaleates (6) and (9). In the case of anisidine (8d), higher oligomers containing three or four azetidine residues, e.g. 10a, were also formed. With more nucleophilic aliphatic amines, only 1:1 adducts of type 7 were obtained. The reaction course can be rationalized by the formation of intermediate zwitterions (11) via addition of the N-nucleophiles onto DCFM. The results show that the nucleophilicity of 1a toward DCFM is lower than that of aliphatic amines but exceeds that of aromatic amines. aromatic amines in dichloromethane at room temperature yielded mixtures of (Z)-2-arylamino-3-cyanofumarates (7) and the corresponding (E)-2-(azetidin-1-yl)-3-cyanomaleates (6) and (9). In the case of anisidine (8d), higher oligomers containing three or four azetidine residues, e.g. 10a, were also formed. With more nucleophilic aliphatic amines, only 1:1 adducts of type 7 were obtained.The reaction course can be rationalized by the formation of intermediate zwitterions (11) show that the nucleophilicity of 1a toward DCFM is lower than that of aliphatic amines but exceeds that of aromatic amines.

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Reaction of 1-Azabicyclo[1.1.0]butane with Activated Amides

Cited by 9 publications

References 26 publications

Efficiency of Lithium Cations in Hydrolysis Reactions of Esters in Aqueous Tetrahydrofuran

Efficiency of Lithium Cations in Hydrolysis Reactions of Esters in Aqueous Tetrahydrofuran

Crystal Structure of 2-(1-Benzoylazetidin-3-yl)thio-1,3-thiazoline

Three-Component Reactions with 3-Phenyl-1-azabicyclo[1.1.0]butane, Dimethyl Dicyanofumarate, and Primary Aromatic Amines

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