51971-47-2

Upstream product

• 85-44-9 phthalic anhydride 
• 2756-85-6 1-aminocyclohexane carboxylic acid 
• 4414-88-4 1H-benzimidazol-2-acetonitrile 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 55278-23-4 1,3,4,4a,5,11a-hexahydro-6H-dibenzo[b,e]azepine-6,11(2H)-dione 
• 2133-65-5 N-cyclohexylphthalimide 

Relevant academic research and scientific papers

Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes

Rhodium(II) azavinyl carbenes, conveniently generated from 1-sulfonyl-1,2,3-triazoles, undergo a facile, mild, and convergent formal 1,3-insertion into N-H and O-H bonds of primary and secondary amides, various alcohols, and carboxylic acids to afford a wide range of vicinally bisfunctionalized (Z)-olefins with perfect regio- and stereoselectivity. Utilizing the distinctive functionality installed through these reactions, a number of subsequent rearrangements and cyclizations expand the repertoire of valuable organic building blocks constructed by reactions of transition-metal carbene complexes, including α-allenyl ketones and amino-substituted heterocycles.

General Access to Modified α-Amino Acids by Bioinspired Stereoselective γ-C?H Bond Lactonization

α-Amino acids represent a valuable class of natural products employed as building blocks in biological and chemical synthesis. Because of the limited number of natural amino acids available, and of their widespread application in proteomics, diagnosis, drug delivery and catalysis, there is an increasing demand for the development of procedures for the preparation of modified analogues. Herein, we show that the use of bioinspired manganese catalysts and H2O2 under mild conditions, provides access to modified α-amino acids via γ-C?H bond lactonization. The system can efficiently target 1°, 2° and 3° γ-C?H bonds of α-substituted and achiral α,α-disubstituted α-amino acids with outstanding site-selectivity, good to excellent diastereoselectivity and (where applicable) enantioselectivity. This methodology may be considered alternative to well-established organometallic procedures.

[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin

Stability constants for the inclusion complexes of cyclohexylphthalimide 2 and adamantylphthalimide 3 with β-cyclodextrin (β-CD) were determined by 1H NMR titration, K = 190 ± 50 M?1, and K = 2600 ± 600 M?1, respectively. Photochemical reactivity of the inclusion complexes 2&at;β-CD and 3&at;β-CD was investigated, and we found out that β-CD does not affect the decarboxylation efficiency, while it affects the subsequent photochemical H-abstraction, resulting in different product distribution upon irradiation in the presence of β-CD. The formation of ternary complexes with acrylonitrile (AN) and 2&at;β-CD or 3&at;β-CD was also essayed by 1H NMR. Although the formation of such complexes was suggested, stability constants could not be determined. Irradiation of 2&at;β-CD in the presence of AN in aqueous solution where cycloadduct 7 was formed highly suggests that decarboxylation and [3 + 2] cycloaddition take place in the ternary complex, whereas such a reactivity from bulky adamantane 3 is less likely. This proof of principle that decarboxylation and cycloaddition can be performed in the β-CD cavity has a significant importance for the design of new supramolecular systems for the control of photoreactivity.

Development of modifiable bidentate amino oxazoline directing group for Pd-catalyzed arylation of secondary C-H bonds

Abstract A novel bidentate α-amino oxazolinyl directing group has been developed. Different from previous directing groups, this newly designed directing group was easily prepared from amino acids and modified in structure. This auxiliary preferentially effects functionalization at secondary C(sp3)-H bonds, rather than at aryl C(sp2)-H bonds. The diastereoselectivity of direct arylation between geminal secondary C(sp3)-H bonds in linear molecules has also been realized for the first time with a chiral directing group by remote chirality relay. Two diastereoisomers are produced with the same chiral source by changing the substituents of substrates and aryl halides. A new direction: A multifunctional amino oxazoline directing group that is readily available from amino acids, has been developed, which can induce chemo-, regio- and diastereoselectivity in secondary C(sp3)-H arylation reactions. Furthermore, this directing group is removable and modifiable. Steric control and counterions play important roles in the relayed chirality transfer.

Cyclic α-amino acids as precursors for synthesis of 2-amino-3-hetarylpyrrolin-4-ones and their spiro derivatives

α-Aminoisobutanoic acid and some representatives of cyclic α-amino acids were converted to corresponding 1-phthalimido- and N-trifluoroacylated acid chlorides. Treatment of 2-(1H-benzimidazol-2-yl) acetonitrile with 1-phthalimidoacid chlorides in DMF unexpectedly gave 2-(1H-benzimidazol-2-yl)-3-(dimethylamino)-2-propenenitrile. On the other hand, the reaction of hetarylacetonitriles with N-trifluoroacylated acid chlorides gave the desired (3-cyano-2-oxo-3-hetarylpropyl)-2,2,2-trifluoroacetamides that upon detrifluoroacetylation provided the target 2-amino-3-hetarylpyrrolin-4- ones. The acylation of benzoimidazolylamino-pyrrolinones by benzoyl chloride leads to formation of 3-benzoyl-2,3-dihydro-5-phenyl-1H-benzo[4,5]imidazo[1,2-c] pyrrolo[3,2-e]pyrimidin-1-ones. Springer-Verlag 2012.

Method for inhibiting bud growth of plants

The invention relates to a method for inhibiting the bud growth of plants by applying to the foliage of the plants, or to soil containing seeds of the plants, a plant-growth-regulating amount of a dihydroimidazoisoindoledione or an optical or stereo isomer thereof.

Method for inhibiting bud growth of plants

The invention relates to a method for inhibiting the bud growth of plants by applying to the foliage of the plants, or to soil containing seeds of the plants, a plant-growth-regulating amount of an imidazoisoindoledione or an optical or stereo isomer thereof.

Method for controlling the relative stem growth of plants

The invention relates to a method for controlling the relative stem growth of plants by applying to the foliage of the plants, or to soil containing seeds of the plants, a plant-growth-regulating amount of a dihydroimidazoisoindoledione or an optical or stereo isomer thereof.

Method for controlling the relative stem growth of plants

The invention relates to a method for controlling the relative stem growth of plants by applying to the foliage of the plants, or to soil containing seeds of the plants, a plant-growth-regulating amount of an imidazoisoindoledione or dihydroimidazoisoindoledione or an optical or stereo isomer thereof.

Imidazoisoindolediones and the use thereof as herbicidal agents

The invention relates to novel imidazoisoindoledione compounds including the optical isomers thereof. This invention also relates to a method for the control of undesirable plant species with the imidazoisoindolediones and their optical isomers, and further, to a process for the preparation of the compounds.