Synthesis of tetracyclic 4H‐benzo[5,6]chromeno[3,4‐d]oxazoles via palladium‐catalyzed intramolecular direct heteroarylation DOI Open Access

Sujeet Kumar,

Km Kajol,

Prakash Nayak

и другие.

Chemistry - An Asian Journal, Год журнала: 2022, Номер 18(3)

Опубликована: Дек. 15, 2022

Abstract We report a palladium‐catalyzed intramolecular direct heteroarylation of oxazole tethered β ‐naphthols to access corresponding tetracyclic 4 H ‐benzo[5,6]chromeno[3,4‐ d ]oxazoles. Various functional groups are well tolerated and furnished the desired products in good excellent yields under present reaction conditions. The scale‐up synthetic utility resulting molecules have been demonstrated. Moreover, UV/vis absorption fluorescence emission properties evaluated for these polyheterocyclic compounds.

Язык: Английский

Non-Decarboxylative Ruthenium-Catalyzed Rearrangement of 4-Alkylidene-isoxazol-5-ones to Pyrazole- and Isoxazole-4-carboxylic Acids DOI Creative Commons
Camilla Loro, L. Molteni, Marta Papis

и другие.

Organic Letters, Год журнала: 2022, Номер 24(16), С. 3092 - 3096

Опубликована: Апрель 19, 2022

Treatment of 4-(2-hydroaminoalkylidenyl)- and 4-(2-hydroxyalkylidenyl)-substituted isoxazol-5(4H)-ones with catalytic amounts [RuCl2(p-cymene)]2, without any additive, afforded pyrazole- isoxazole-4-carboxylic acids, respectively. The presence an intramolecular H-bond in these substrates was the key to divert classical mechanism toward a ring-opening non-decarboxylative path that is expected generate vinyl Ru-nitrenoid intermediate, cyclization which affords rearranged products. A gram scale protocol demonstrated synthetic applicability this transformation.

Язык: Английский

Процитировано

11

Copper-Catalyzed/Hypervalent Iodine-Mediated Functionalization of Unactivated Compounds DOI Open Access
Marta Papis, Francesca Foschi, Sara Colombo

и другие.

Catalysts, Год журнала: 2023, Номер 13(9), С. 1243 - 1243

Опубликована: Авг. 26, 2023

The functionalization of unactivated substrates through the combination copper catalysts and hypervalent iodine reagents represents a versatile tool in organic synthesis to access various classes compounds. derivatives can be used simply as oxidizing agents regenerate catalytic species or they associate starting material. In this review, special attention will paid methodologies which provide introduction nucleophiles into reagent by use suitable benziodoxol(on)es iodonium salts. Many reactions concern C- N-arylations, but may also involve formation different carbon–carbon carbon–nitrogen bonds, carbon–oxygen well carbon–halogen carbon–phosphorus bonds.

Язык: Английский

Процитировано

6

Palladium‐Catalyzed/Mn(OAc)3‐Mediated 1,2‐Diazidation and 1,2‐Acetoxy/Hydroxylation of N‐Allyl Sulfonamides DOI Creative Commons
Marta Papis, Sara Colombo, Leonardo Lo Presti

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(11), С. 2477 - 2482

Опубликована: Апрель 11, 2024

Abstract Palladium‐catalyzed conditions for diazidation or acetoxy/hydroxylation of N ‐allyl sulfonamides by using Pd(OAc) 2 as the catalyst combined with Mn(OAc) 3 ⋅ 2H O have been developed. The 1,2‐diazidation reaction carbon‐carbon double bond occurs in mild ( i. e . NaN azide source THF at room temperature), whereas 1,2‐acetoxy/hydroxylation requires an excess O. well‐known ability this reagent to act through single‐electron transfer (SET) makes plausible a radical mechanism involving high valent palladium complexes.

Язык: Английский

Процитировано

2

Ruthenium‐Catalyzed Decarboxylative Rearrangement of 4‐Alkenyl‐isoxazol‐5‐ones to Pyrrole Derivatives DOI
L. Molteni, Camilla Loro, Michael S. Christodoulou

и другие.

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(25)

Опубликована: Июнь 6, 2022

Abstract Easily accessible isoxazol‐5(4 H )‐ones are useful precursors of heterocycles. In this context, we report the ruthenium‐catalyzed transformation 4‐alkenyl‐substituted isoxazol‐5‐ones to afford 1 ‐pyrrole derivatives. The operative conditions were proven be effective also on cyclohexane‐fused isoxazolones giving 4,5,6,7‐tetrahydroindoles. reactions, which allow for access tri‐and tetra‐substituted pyrroles in moderate high yields, occur through decarboxylative ring‐opening/ring‐closure involving C−H functionalization alkenyl moiety.

Язык: Английский

Процитировано

10

Tandem Copper(I)‐Catalyzed N‐Arylation–1,4‐Conjugate Addition to Access Tetrahydroacridinones DOI

Jyoti M. Honnanayakanavar,

Purna Chandra Behera,

Surisetti Suresh

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(23), С. 4043 - 4048

Опубликована: Окт. 29, 2022

Abstract A copper‐catalyzed tandem process integrating N ‐arylation and 1,4‐conjugate addition is disclosed through the reaction of cyclic enaminones ortho ‐halochalcones. The appears to proceed chemoselective arylation on nitrogen enaminone with ‐halochalcones Michael α‐carbon chalcone furnish a diverse range tricyclic tetrahydroacridinone derivatives in moderate excellent yields. magnified image

Язык: Английский

Процитировано

10

Copper(II)-Catalyzed Three-Component Arylation/Hydroamination Cascade from Allyl Alcohol: Access to 1-Aryl-2-sulfonylamino-propanes DOI Creative Commons
Camilla Loro, Marta Papis, Francesca Foschi

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(19), С. 13995 - 14003

Опубликована: Сен. 25, 2023

A new straightforward approach to 1-aryl-2-aminopropanes using easily accessible substrates has been developed. Simple allyl alcohol is shown be an ideal synthetic equivalent of the C3 propane-1,2-diylium bis-cation synthon in three-component cascade reactions with arenes and sulfonamide nucleophiles regioselectively afford 1-aryl-2-aminopropanes. The reaction catalyzed by Cu(OTf)2 expected involve a Friedel-Crafts-type allylation arene, followed hydroamination.

Язык: Английский

Процитировано

5

Methanol as a C1 Source for the Synthesis of 1,3‐Polyheterocyclic Systems DOI Creative Commons
L. Molteni, Egle M. Beccalli, Laura Castoldi

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(48)

Опубликована: Ноя. 13, 2023

Abstract A very attractive approach toward 1,3‐polyheterocyclic systems was provided exploiting the copper‐catalyzed reaction of aminoalcohols and diaminoalkanes, in oxidative conditions presence methanol. The synthetic pathway showed involvement methanol both as solvent a reagent, making procedure particularly efficient sustainable for synthesis five‐, six‐, seven‐membered polyheterocyclic rings.

Язык: Английский

Процитировано

4

Synthesis and Characterisation of Fluorescent Novel Pt(II) Cyclometallated Complexes with Anticancer Activity DOI Open Access
Brondwyn S. McGhie, Jennette A. Sakoff, Jayne Gilbert

и другие.

International Journal of Molecular Sciences, Год журнала: 2023, Номер 24(9), С. 8049 - 8049

Опубликована: Апрель 28, 2023

Cancer poses a significant threat to global health and new treatments are required improve the prognosis for patients. Previously, unconventional platinum complexes designed incorporate polypyridyl ligands paired with diaminocyclohexane have demonstrated anticancer activity in KRAS mutated cells, previously thought be undruggable cytotoxicity values up 100 times better than cisplatin. In this work, these were used as inspiration design six novel cyclometallated examples, whose fluorescence could exploited understand mechanism of action kinds drugs. The results revealed that (CMCs) significantly different compared inspired them; they cytotoxic cisplatin much higher selectivity indices breast cancer cell lines (MCF10A/MCF-7). Complexes 1b, 2a, 3b all had very high indexes previous Pt(II) complexes. This prompted further investigation into their DNA binding properties, which good affinity ctDNA, especially CMCs 1a 3b. Their inherent was successfully utilised calculation useful future work.

Язык: Английский

Процитировано

3

Phosphine-Catalyzed Domino Regio- and Stereo-Selective Hexamerization of 2-(Bromomethyl)acrylates to 1,2-Bis(cyclohexenyl)ethenyl Derivatives DOI Creative Commons
Marta Papis, Raffaella Bucci, Alessandro Contini

и другие.

Organic Letters, Год журнала: 2023, Номер 25(40), С. 7380 - 7384

Опубликована: Сен. 29, 2023

A phosphine-catalyzed domino assembly of six units 2-bromomethyl acrylates afforded polyalkenyl adducts containing two cyclohexenyl rings. This reaction occurs under mild conditions providing the final product by formation seven carbon-carbon bonds and four stereocenters. Experimental computational studies support an initial dimerization substrate, which in turn trimerizes involving totally regio- stereocontrolled Diels-Alder cycloadditions. The yield hexamerization depends on size ester function. protocol has also proved to be practicable a gram scale.

Язык: Английский

Процитировано

3

Synthesis of morpholino nucleosides starting from enantiopure glycidol DOI
Marta Papis, Camilla Loro, Michele Penso

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(11), С. 2949 - 2954

Опубликована: Янв. 1, 2022

A rapid synthesis of morpholino monomers from readily available building blocks is reported.

Язык: Английский

Процитировано

4