Cadmium chloride-catalyzed regioselective opening of oxiranes with aromatic amines — An improved protocol for the synthesis of 2-amino alcohols

2007 ◽  
Vol 85 (1) ◽  
pp. 37-41 ◽  
Author(s):  
S Ramesh Kumar ◽  
P Leelavathi
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Cadmium Chloride ◽  
Room Temperature ◽  
Amino Alcohols ◽  
Reaction Conditions ◽  
Ring Opening Reaction

Epoxides undergo rapid CdCl2-catalyzed ring-opening reaction with aromatic amines in mild reaction conditions (room temperature), affording the corresponding 2-amino alcohols with high regioselectivity.Key words: epoxides, aromatic amines, cadmium chloride, 2-amino alcohols.

scholarly journals Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts

RSC Advances ◽  
2018 ◽  
Vol 8 (49) ◽  
pp. 28139-28146 ◽  
Author(s):  
Koichi Tanaka ◽  
Maya Kinoshita ◽  
Jun Kayahara ◽  
Yutaro Uebayashi ◽  
Kazusada Nakaji ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Heterogeneous Catalysts ◽  
Metal Organic Framework ◽  
Metal Organic Frameworks ◽  
Amino Alcohols ◽  
Ring Opening Reaction ◽  
Ring Opening Reactions ◽  
Metal Organic ◽  
Asymmetric Ring Opening

Asymmetric ring-opening reactions of meso-epoxides by aromatic amines were achieved by using some chiral metal–organic frameworks. The corresponding β-amino alcohols were obtained with good yields and enantioselectivities (up to 97% ee).

Regio- and Stereoselective Synthesis of a Novel Family of Unsaturated Compounds with the S–Se Bond and Their Cyclization to 2,3-Dihydro-1,4-thiaselenines

Synthesis ◽  
2019 ◽  
Vol 51 (08) ◽  
pp. 1832-1840 ◽  
Author(s):  
Svetlana Amosova ◽  
Andrey Filippov ◽  
Vladimir Potapov ◽  
Maxim Penzik ◽  
Nataliya Makhaeva ◽  
...  
Keyword(s):  
Ring Opening ◽  
Room Temperature ◽  
Stereoselective Synthesis ◽  
Reaction Times ◽  
Nucleophilic Attack ◽  
Selenium Atom ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Ring Opening Reaction ◽  
Acid Catalyzed

Regio- and stereoselective ring-opening reaction of 2-bromomethyl-1,3-thiaselenole with thiols proceeded as nucleophilic attack at the selenium atom of seleniranium intermediate affording unsaturated selanyl sulfides, (Z)-CH2=CHSCH=CHSeSR, in up to 93% yield. Dithiols were involved in this reaction giving symmetrical polyunsaturated compounds with two S–Se bonds in 70–75% yields. Efficient synthesis of 2-(organylsulfanyl)-2,3-dihydro-1,4-thiaselenines in 69–96% yields was developed by the acid-catalyzed cyclization of the unsaturated selanyl sulfides. Mild reaction conditions (room temperature) and short reaction times are important features of this methodology.

scholarly journals REACTION OF 2-HETARYL-2-(DIHYDROFURAN-2(3H)-ILIDEN)ACETONITRILES WITH AROMATIC AMINES

2020 ◽  
pp. 47-51
Author(s):  
R. Shemehen ◽  
O. Khilya ◽  
Yu. Volovenko
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Catalytic Amount ◽  
Building Blocks ◽  
Heterocyclic Ring ◽  
Ring Closure ◽  
Reaction Conditions ◽  
Ring Opening Reaction ◽  
Ring Transformations ◽  
High Yields

This article reports on the reaction of 2-hetaryl-2-(furanyl-2-ylidene)acetonitriles with aromatic amines as N-nucleophiles. 2-Hetaryl-2-(furanyl-2-ylidene)acetonitriles represent versatile building blocks in syntheses of ω-(N-aryl)alkyl substituted heterocycles due to the presence of 1,3-bielectrophilic acrylonitrile fragment functionalized with unsaturated heterocyclic ring and nucleophilic azaheterocyclic moiety. The carbonyl group masked within the N-arylpyrrolidinylidene fragment which undergoes a ring opening through the reaction with nucleophiles. So, a method for the synthesis of 2-hetaryl-6-hydroxy-3-(arylamino)hex-2-enenitriles and 2-hetaryl-2-(N-arylpyrrolidin-2-ylidene)acetonitriles has been developed by us. The proposed scheme is based on the available reagents using. As a result of Michael addition, the aromatic amines to 2-hetaryl-2-(furanyl-2-ylidene)acetonitriles followed by ring transformations has formed two types of products, depending on the reaction conditions. The reaction of substituted furanylylideneacetonitriles with aromatic amines proceeds in good to high yields affording the corresponding 3-(arylamino)hex-2-enenitriles and 2-(N-arylpyrrolidin-2-ylidene)acetonitriles derivatives. The stereochemistry of the ring-opening reaction follows the rules of a classical SN2 mechanism. The resulting linear products can be cyclized to 2-hetaryl-2-(furanyl-2-ylidene)acetonitriles in high yields by treatment with the catalytic amount of acid or the equimolar amount of aromatic amines. Under these conditions 2-hetaryl-6-hydroxy-3-(arylamino)hex-2-enenitriles arising from reaction gives the ring closure. Since both ring-opening and cyclisation occur with fixed stereochemistry the reaction appears a valuable modification to the preparation of acetonitriles derivatives.

scholarly journals Anhydrous Titanium(III) chloride as a New Lewis-Acid Catalyst for Ring Opening of Epoxides with Aromatic Amines

2007 ◽  
Vol 2 (2) ◽  
pp. 1934578X0700200
Author(s):  
Suchitra Bhatt ◽  
Sandip K. Nayak
Keyword(s):  
Ambient Temperature ◽  
Lewis Acid ◽  
Aromatic Amines ◽  
Ring Opening ◽  
Acid Catalyst ◽  
Amino Alcohols ◽  
Azide Ion ◽  
Ring Opening Of Epoxides ◽  
Lewis Acid Catalyst

Anhydrous titanium(III) chloride was found to be a simple and efficient Lewis acid catalyst for ring opening of epoxides at ambient temperature. The reaction proceeded smoothly with anilines as well as azide ion as nucleophiles to give the corresponding β-amino alcohols and β-azido alcohols in moderate to good yields.

scholarly journals An efficient and atom-economical route to N-aryl amino alcohols from primary amines

RSC Advances ◽  
2018 ◽  
Vol 8 (60) ◽  
pp. 34304-34308 ◽  
Author(s):  
Zhen Xiao ◽  
Juanjuan Li ◽  
Qiang Yue ◽  
Qian Zhang ◽  
Dong Li
Keyword(s):  
Ring Opening ◽  
Amino Alcohols ◽  
Primary Amines ◽  
Ring Opening Reaction ◽  
Novel Method

A novel method for generation of N-aryl amino alcohols from N,N-disubstituted picolinamides through reduction/ring-opening reaction with NaBH4 was developed.

scholarly journals Ionic Liquid Catalyzed Per-O-Acetylation and Benzylidene Ring-Opening Reaction

Catalysts ◽  
2020 ◽  
Vol 10 (6) ◽  
pp. 642 ◽  
Author(s):  
Mayur Thul ◽  
Yao-Peng Wu ◽  
Yi-Jyun Lin ◽  
Shu-Lin Du ◽  
Hsin-Ru Wu ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Ring Opening ◽  
Room Temperature ◽  
Catalytic Amount ◽  
Atom Economy ◽  
Selective Catalyst ◽  
Imidazolium Ionic Liquids ◽  
Ring Opening Reaction ◽  
Brönsted Acid

Tunable aryl imidazolium ionic liquids acting as Brønsted acid ionic liquids were found to be efficient catalysts for per-O-acetylation and reductive ring opening of benzylidene acetals. This method requires a truly catalytic amount of the least expensive available ionic liquids that are water-stable and reusable and also stable at room temperature. The reactions were obtained in one hour with good to excellent yields. These reactions can form C−O and C−H bonds with a high atom economy. Furthermore, the ionic liquid is an anomeric selective catalyst in per-O-acetylation and reductive ring opening of benzylidene acetals of sugar moieties.

Highly regioselective ring-opening of epoxides with amines: a metal- and solvent-free protocol for the synthesis of β-amino alcohols

2020 ◽  
Vol 56 (15) ◽  
pp. 2256-2259
Author(s):  
Dong Li ◽  
Jing Wang ◽  
Shibo Yu ◽  
Silei Ye ◽  
Wenjie Zou ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Ring Opening ◽  
Amino Alcohols ◽  
Solvent Free ◽  
Ring Opening Reaction ◽  
Ring Opening Of Epoxides

We herein report a metal- and solvent-free acetic acid-mediated ring-opening reaction of epoxides with amines.

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