Diastereoselective 2,3-diazidation of indoles via copper(II)-catalyzed dearomatization

The copper-catalyzed directed dearomatization of indoles with the assistance of directing groups has been developed for the synthesis of 2,3-diazido indolines with good yields and excellent diastereoselectivities in aqueous solution. The resultant 2,3-diazides can be smoothly converted to other functional groups, including vicinal diamines, triazoles and benzotriazoles, in a single step.     

Synthesis of diisocyanides with phenolic groups and their polymerization to helically chiral poly(quinoxaline‐2,3‐diyl)s

The development of synthetic routes which lead to five new diisocyanide monomers with one or two phenolic groups is described. Their polymerization behavior is studied with Pd‐ and Ni‐based initiators, as well as under microwave irradiation. The polymerizability is mainly dominated by steric effects as is concluded from experiments using different protecting groups. Chiroptical properties of these new polymers are studied by CD‐spectroscopy. After deprotection, helically chiral poly(quinoxalin‐2,3‐diyl)s are obtained which display a Brønsted function attached to a stereolabile biaryl axis whose configuration should be influenced by the chiral polymer backbone. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015 , 53, 1320–1329     

Sulfonic acid-functionalized Fe3O4-supported magnetized graphene oxide quantum dots: A novel organic-inorganic nanocomposite as an efficient and recyclable nanocatalyst for the synthesis of dihydropyrano[2,3-c]pyrazole and 4H-chromene derivatives

In this research, the main emphasis has been focused on the preparation of a novel Fe₃O₄-supported propane-1-sulfonic acid-grafted graphene oxide quantum dots (Fe₃O₄@GOQD-O-(propane-1-sulfonic acid)) that it was readily synthesized via a five-step procedure as a hitherto unreported magnetic nanocatalyst. This newly prepared Fe₃O₄@GOQD-O-(propane-1-sulfonic acid) nanocomposite was structurally well-established by different analytical techniques including Fourier transform infrared (FT-IR), X-ray diffraction (XRD), energy-dispersive X-ray (EDX), thermal gravimetric analysis (TGA), field emission gun-scanning electron microscope (FESEM), high-resolution transmission electron microscopy (HRTEM) and vibrating sample magnetometer (VSM) analyses. The high catalytic performance of this nanocomposite was exhibited in one-pot synthesis of dihydropyrano[2,3-c]pyrazole and 4H-chromene derivatives under mild conditions. Low reaction times, excellent yields of the products, benignity of the catalyst, easy reaction work-up and magnetic recyclability of the catalyst are the main advantages of the present protocol. Also, our research indicated that the Fe₃O₄@GOQD-O-(propane-1-sulfonic acid) could be reused up to five times without considerable loss of catalytic activity.     

Study of all stages of the Diels–Alder reaction of cyclopentadiene with 2,3-dicyano-1,4-benzoquinone and monoadducts: Kinetics,thermochemistry, and high pressure effect

The kinetic parameters and enthalpies of the Diels–Alder reactions between cyclopentadiene and 2,3-dicyano-1,4-benzoquinone leading to the formation of two different monoadducts and bisadduct were determined. The stability of adducts is compared. Monoadduct appears to be thermodynamically more stable than the bisadduct. Comparison with the other Diels–Alder reactions studied previously allows us to conclude that the heat effects upon formation of the considered Diels–Alder adducts are the lowest in comparison with all the studied dienophiles.     

Sulfinyl-Mediated Stereoselective Functionalization of Acyclic Conjugated Dienes

The chemo- and stereocontrolled functionalization of conjugated sulfinyl dienes in a cascade process that involves a conjugate addition, diastereoselective protonation and a [2,3]-sigmatropic rearrangement is reported. Enantioenriched 1,4-diol and 1,4-aminoalcohol derivatives are obtained in a very straightforward manner. Further functionalization of these structures, including highly stereoselective epoxidation, dihydroxylation and the stereodivergent synthesis of several polyols in a controlled fashion is described.     

Fe3O4‐supported Schiff‐base copper (II) complex: A valuable heterogeneous nanocatalyst for one‐pot synthesis of new pyrano[2,3‐b]pyridine‐3‐carboxamide derivatives

A novel Cu (II) Schiff‐base complex immobilized on core‐shell magnetic Fe₃O₄ nanoparticles (Fe₃O₄@SPNC) was successfully designed and synthesized. The structural features of these nanoparticles were studied and confirmed by using various techniques including FT‐IR spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy‐dispersive X‐ray spectroscopy (EDS), vibrating sample magnetometer (VSM), X‐Ray diffraction (XRD), wavelength dispersive X‐ray spectroscopy (WDX), and inductively coupled plasma (ICP). These newly synthesized nanoparticles have been used as efficient heterogeneous catalytic system for one‐pot multicomponent synthesis of new pyrano[2,3‐b]pyridine‐3‐carboxamide derivatives. Notably, the catalyst could be easily separated from the reaction mixture by using an external magnet and reused for several successive reaction runs with no significant loss of activity or copper leaching. The present protocol benefits from a hitherto unreported MNPs‐immobilized Cu (II) Schiff‐base complex as an efficient nanocatalyst for the synthesis of newly reported derivatives of pyrano[2,3‐b]pyridine‐3‐carboxamide from one‐pot multicomponent reactions.     

CoFe2O4@SiO2‐CPTES‐Guanidine‐Cu(II): A novel and reusable nanocatalyst for the synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones and polyhydroquinolines and oxidation of sulfides

CoFe₂O₄@SiO₂‐CPTES‐Guanidine‐Cu(II) magnetic nanoparticles were synthesized and used as a new, inexpensive and efficient heterogeneous catalyst for the synthesis of polyhydroquinolines and 2,3‐dihydroquinazoline‐4(1H)‐ones and for the oxidation of sulfides. The structure of this nanocatalyst was characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, energy‐dispersive X‐ray spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, X‐ray diffraction and inductively coupled plasma optical emission spectrometry. Simple preparation, high catalytic activity, simple operation, high yields, use of green solvents, easy magnetic separation and reusability of the catalyst are some of the advantages of this protocol.     

Coordination and extraction properties of new bis- and tetrakis(diphenylphosphoryl)-substituted pyrazines towards f-block elements

2,3-Bis- and 2,3,5,6-tetrakis(diphenylphosphoryl)-substituted pyrazines have been synthesized from the corresponding polychloropyrazines and ethyl diphenylphosphinite. They may serve as new N,O-bidentate organophosphorus ligands for extraction and recovery of f-block metal ions from nitric acid solutions.     

A simple synthesis of natural spinazarins and their analogues

A short simple synthesis of spinazarins (2,3-dihydroxy-naphthazarins or 2,3,5,8-tetrahydroxy-1,4-naphtho-quinones) from available 2,3-dichloronaphthazarin derivatives involves replacement of chlorine atoms with azido groups followed by their acidic hydrolysis. The procedure can be used for the preparative synthesis of natural biologically active spinazarins and their analogues.     

哌啶并[2,3-b]哌嗪类衍生物的设计、合成及其抗血小板聚集活性研究

以2,3-二氨基吡啶和2,3-丁二酮为起始原料,经环化、催化氢化和亲核取代反应合成了10个新型哌啶并[2,3-b]哌嗪类衍生物(3a~3j),其结构经¹H NMR、¹³C NMR和HR-MS确证。体外抗血小板聚集活性研究表明,化合物3d、3e、3g、3h和3j具有一定的抗血小板聚集作用,其中化合物3h(IC₅₀=1.24mmol/L)的活性显著优于母体化合物川芎嗪(IC₅₀=3.96mmol/L)和阳性药物阿司匹林(IC₅₀=2.41mmol/L)。