82323-45-3Relevant academic research and scientific papers
Efficient Approaches for the Synthesis of Diverse α-Diazo Amides
Arter, Christopher,Chow, Shiao,Green, Adam I.,Karageorgis, George,Leggott, Abbie,Liver, Samuel,Nelson, Adam,Trask, Luke,Warriner, Stuart
supporting information, p. 1695 - 1706 (2020/05/25)
Metal-catalysed carbenoid chemistry can be exploited for the synthesis of diverse ranges of small molecules from α-diazo carbonyl compounds. In this paper, three synthetic approaches to α-diazo amides are described, and their scope and limitations are determined. On the basis of these synthetic studies, recommendations are provided to assist the selection of the most appropriate approach for specific classes of product. The availability of practical and efficient syntheses of diverse α-diazo acetamides is expected to facilitate the discovery of many different classes of bioactive small molecules.
Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines
Li, Long,Zhou, Bo,Wang, Yong-Heng,Shu, Chao,Pan, Yi-Fei,Lu, Xin,Ye, Long-Wu
supporting information, p. 8245 - 8249 (2015/07/07)
An efficient zinc(II)-catalyzed alkyne oxidation/C￡H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of isoquinolones and β-carbolines. Importantly, in contrast to the well-established gold-catalyzed intermolecular alkyne oxidation, over-oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theoretical calculations are described.
Cyclopropene Photochemistry. Mechanistic and Exploratory Organic Photochemistry
Zimmerman, Howard E.,Bunce, Richard A.
, p. 3377 - 3396 (2007/10/02)
Four new cyclopropenes have been synthesized and their photochemistry has been investigated.Thus, 3-methyl-1,2-diphenyl-3-(2-phenylallyl)cyclopropene was found on direct photolysis to afford four photoproducts, the two major products of which derived from novel photochemistry. 2-Methylene-4-methyl-5,6-diphenyltetracyclo1,504,6>undeca-8,10-diene derived from cycloaddition of the excited cyclopropenyl ? bond to the C-1,C-2 ? bond of the phenyl of the 2-phenylallyl side chain.The quantum yield for this novel transformation was 0.023.A second photoproduct was 2-methyl-1,4,6-triphenyltricyclo2,6>hexane.This product results from a formal cycloaddition of the excited cyclopropenyl ? bond to the allyl double bond.A diradical mechanism is structurally equivalent.Formation of such a tricyclic 2,6> system is normally not found in direct irradiations.The quantum yield for this product was 0.088.Also formed was 3-methyl-1,2,5-triphenylbicyclohex-2-ene with an efficiency of 0.019.This product is understood as deriving either (i) from cyclopropene opening to a carbene which then adds to the allyl ? bond or (ii) from a bicyclic diradical arising from vinyl-vinyl bonding.The fourth photoproduct is 2-methyl-1,3-diphenyl-3-(2-phenylallyl)cyclopropene.The efficiency was 0.018.The bicyclic diradical above provides a common species leading to the last three products.Sensitization led only to the first two products: the tetracyclic diene (φ=0.26) and the tricyclo2,6>hexane (φ=0.15).Product structures were established by X-ray, degradation, independent synthesis, and spectral analysis.In addition, the photochemistry of cis- and trans-2,6-dimethyl-1,6-diphenylspirooct-1-ene was investigated.Stereoisomerization resulted from the singlet but not the triplet.Mechanisms for the above transformations are considered.Finally, corresponding thermal chemistry exhibited by the above compounds was investigated.
