2026-08-6Relevant articles and documents
Enantiocontrolled macrocycle formation by catalytic intramolecular cyclopropanation
Doyle, Michael P.,Hu, Wenhao,Chapman, Brant,Marnett, Alan B.,Peterson, Chad S.,Vitale, Justin P.,Stanley, Sarah A.
, p. 5718 - 5728 (2000)
Stereoselectivity in intramolecular cyclopropanation reactions resulting in cyclopropane fusion with ten- and larger-membered rings has been examined using chiral copper(I) and dirhodium(II) catalysts. The influence of alkene structure and catalyst has be
Mild and efficient synthesis of 1,8-naphthalide and 1,8- naphthalenedimethanol
Luo, Huan,Zeng, Qingle,Liu, Zhongrong,Wei, Yongzhi,Li, Bogang,Wang, Fengpeng
, p. 2269 - 2275 (2004)
Mild and efficient procedures have been developed for synthesis of 1,8-naphthalide and 1,8-naphthalenedimethanol. In an ice-water bath, 1,8-naphthalide was prepared from 1,8-naphthlic anhydride using LiAlH 4 as reducing agent. 1,8-Naphthalenedi
Platinum-on-Carbon-Catalyzed Aqueous Oxidative Lactonization of Diols by Using Molecular Oxygen
Ban, Kazuho,Sajiki, Hironao,Sawama, Yoshinari,Takakura, Ryoya
supporting information, p. 1919 - 1923 (2019/09/30)
A lactonization of various diols catalyzed by platinum on carbon (Pt/C) in water under an atmosphere of molecular oxygen was developed. Derivatives of 1,4- 1,5- and 1,6-diols were transformed into the corresponding five-, six-, and seven-membered lactones by the present oxidative lactonization method.
Eight-membered-ring diaminocarbenes bearing naphthalene moiety in the backbone: DFT studies, synthesis of amidinium salts, generation of free carbene, metal complexes, and solvent-free copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction
Chesnokov, Gleb A.,Topchiy, Maxim A.,Dzhevakov, Pavel B.,Gribanov, Pavel S.,Tukov, Aleksandr A.,Khrustalev, Victor N.,Asachenko, Andrey F.,Nechaev, Mikhail S.
supporting information, p. 4331 - 4345 (2017/04/03)
A new type of eight-membered ring N-heterocyclic carbene (NHC) bearing a rigid naphthalene moiety in the backbone is reported for the first time. Stereoelectronic properties of 4,5-dihydro-1H-naphtho[1,8-ef][1,3]diazocin-3(2H)-ylidene (NaphtDHD) and small
Intramolecular Parallel [4+3] Cycloadditions of Cyclopropane 1,1-Diesters with [3]Dendralenes: Efficient Construction of [5.3.0]Decane and Corresponding Polycyclic Skeletons
Zhang, Chi,Tian, Jun,Ren, Jun,Wang, Zhongwen
supporting information, p. 1231 - 1236 (2017/02/05)
Aiming to develop efficient and general strategies for construction of complex and diverse polycyclic skeletons, we have successfully developed [4+3]IMPC (intramolecular parallel cycloaddition) of cyclopropane 1,1-diesters with [3]dendralenes. With a combination of the [4+3]IMPC and subsequent [4+n] cycloadditions, trans-[5.3.0]decane skeleton and its corresponding structurally complex and diverse polycyclic variants could be constructed efficiently. This novel [4+3] cycloaddition reaction mode of donor–acceptor cyclopropanes proceeds as a result of the ring-strain relief of a trans-[3.3.0]octane. We strongly believe that the developed methods will demonstrate potential applications in natural products synthesis and drug discovery.
1-Aminobenzocyclobutene-1-phosphonic Acid and Related Compounds as Inhibitors of Phenylalanine Ammonia-Lyase
Zoń, Jerzy,Miziak, Piotr
, (2017/05/17)
Five new geminal aminocycloalkanephosphonic acids (4 – 8) containing both an aromatic ring and a cycloalkane ring were synthesized and evaluated as potential inhibitors of buckwheat phenylalanine ammonia-lyase (PAL). Within the set of compounds which are related to 2-aminoindane-2-phosphonic acid (AIP, 3), a known powerful inhibitor of PAL, racemic 1-aminobenzocyclobutene-1-phosphonic acid (4), was six times weaker than AIP as an in vitro inhibitor of buckwheat PAL, but six times stronger than AIP as an in vivo inhibitor of phenylalanine-derived anthocyanin synthesis in buckwheat.
Merging Photoredox with Br?nsted Acid Catalysis: The Cross-Dehydrogenative C?O Coupling for sp3 C?H Bond Peroxidation
Xia, Qing,Wang, Qiang,Yan, Changcun,Dong, Jianyang,Song, Hongjian,Li, Ling,Liu, Yuxiu,Wang, Qingmin,Liu, Xiangming,Song, Haibin
supporting information, p. 10871 - 10877 (2017/08/18)
A photoredox and Br?nsted acid synergistically catalyzed cross-dehydrogenative C?O coupling reaction is developed in which isochroman peroxyacetals are formed through sp3 C?H bond peroxidation. The reported method is characterized by its extremely mild reaction conditions, excellent yields, and broad substrate scope. An oxocarbenium ion p-chlorobenzenesulfonate was speculated to be the reactive intermediate. The role of hemiacetals and oxygenated dimers on the effective stabilization of the oxocarbenium ion was investigated; the presence of acid appeared to establish equilibrium between hemiacetals and oxygenated dimers with the oxocarbenium ion pairs. The broad applicability of the method highlights the potential of the protocol for molecule synthesis.
Dioxomolybdenum Complexes as Excellent Catalysts for the Deoxygenation of Aryl Ketones to Aryl Alkenes
Fernandes, Tiago A.,Fernandes, Ana C.
, p. 3503 - 3507 (2015/11/10)
This work describes a new methodology for the selective deoxygenation of aryl ketones to the corresponding aryl alkenes catalyzed by dioxomolybdenum complexes using silanes as reducing agents. The best results were obtained with the system PhSiH3/MoO2Cl2(H2O)2 (5-10 mol %), which was very efficient for the deoxygenation of a large variety of aryl ketones to alkenes in excellent yields. This new methodology has the advantages of using an inexpensive, environmentally friendly, easily prepared, and air-stable catalyst in ether solution.
Iron(II) pincer-catalyzed synthesis of lactones and lactams through a versatile dehydrogenative domino sequence
Pea-Lpez, Miguel,Neumann, Helfried,Beller, Matthias
, p. 865 - 871 (2015/03/14)
The synthesis of lactones and lactams by using iron(II) pincer-catalyzed dehydrogenative methodology was developed. Starting from 1,n-diols or 1,n-amino alcohols, this domino transformation takes place through initial dehydrogenation of the substrates, subsequent intramolecular cyclization, and final oxidation to afford the desired products in good yields. The ability to access heterocycles of different sizes makes this protocol especially versatile, in which two consecutive oxidation reactions are performed without requiring an external oxidant. In this paper, we report the application of the Fe-MACHO-BH complex [carbonylhydrido(tetrahydroborato)[bis(2-diisopropylphosphinoethyl)amino]iron(II)] in this atom-efficient and environmentally benign process, for which molecular hydrogen is formed as the only stoichiometric side product. Just a little pinch: The iron(II) pincer-catalyzed synthesis of lactones and lactams from easily available 1,n-diols and 1,n-amino alcohols is explored. The use of a nontoxic metal as well as the generation of molecular hydrogen as the only stoichiometric byproduct makes this method a highly atom-efficient and environmentally benign process.
HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF
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Paragraph 00335; 00392, (2014/07/21)
Provided herein are heterocyclyl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.
