Incorporation of molecular nitrogen into organic compounds

Uozumi, Yasuhiro; Mori, Eiko; Mori, Miwako; Shibasaki, Masakatsu

doi:10.1016/0022-328x(90)80087-g

Cited by 31 publications

(8 citation statements)

References 7 publications

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“…Thus, the carbonylation of 8 b (R 1 =Me, R 2 =H) yields a single isomer, 18 b , for which NOESY experiments reveal the same Z configuration of the CC bond present in 8 b . This selectivity contrasts with previous results on the generation of related lactones, obtained as mixtures of their Z and E isomers,20 and has been used as structural probe for the nature of the products resulting from the reactions of 8 a with MeC(O)H and PhC(O)H, to be discussed below.…”

Section: Resultsmentioning

confidence: 73%

Cyclic Enolates of Ni and Pd: Equilibrium between C‐ and O‐Bound Tautomers and Reactivity Studies

Cámpora¹,

Maya²,

Carmona³

et al. 2005

Chemistry A European J

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2-acylaryl complexes of Ni and Pd containing chelating diphosphines react with KtBuO to give metallacyclic enolate complexes. While coordination through the carbon atom is preferred in the case of Pd, the nickel O-enolate compounds are formed as the corresponding O-tautomers. Slow equilibration between O- and C-enolate tautomers is observed for the nickel complex with an unsubstituted enolate function (M-O-C=CH(2)). Theoretical DFT calculations suggest that the barrier for the tautomer exchange has its origin in the rigidity of the metallacycle. Whilst the C-enolate tautomer is unreactive towards aldehydes, the corresponding O-enolate adds to MeCHO and PhCHO, giving rise to products that retain the enolate functionality. The carbonylation of these products cleanly leads to the formation of enol lactones in a highly selective manner.

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Section: Resultsmentioning

confidence: 73%

Cyclic Enolates of Ni and Pd: Equilibrium between C‐ and O‐Bound Tautomers and Reactivity Studies

Cámpora¹,

Maya²,

Carmona³

et al. 2005

Chemistry A European J

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“…When compound (8a) was reacted with Pd(PPh 3 ) 4 in NMP at 100 °C for 12 h under carbon monoxide, enol lactone (12a) was obtained in 87% yield. 17 Then, compound (12a) was reacted with 2 in NMP at 120 °C for 24 h to give isoindolinone (9a) in 80% yield. Various isoindolinones could be synthesized using this procedure and the results are shown in Table 1.…”

Section: Scheme 4 Plan For Synthesis Of Isoindolinonementioning

confidence: 99%

“…A NMP solution of N-acetyl-2-bromoaniline derivative (14), Pd(PPh 3 ) 4 , 2 and K 2 CO 3 was heated under carbon monoxide at 100 °C overnight to afford glycosminine in 40% yield. The reaction course would be same as that of isoindolinone, that is, acylpalladium complex (16) would react with an enol part of 16 to afford benzoxazinone (17). Then it reacts with 2 to afford glycosminine.…”

Section: Scheme 4 Plan For Synthesis Of Isoindolinonementioning

confidence: 99%

Synthesis of Nitrogen Heterocycles Utilizing Molecular Nitrogen as a Nitrogen Source and Attempt to Use Air Instead of Nitrogen Gas

Mori¹

2009

HETEROCYCLES

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Nitrogen fixation using transition metals is a challenging subject. Using a titanium-nitrogen complex, discovered by Yamamoto in 1967, and titanium isocyanate complex, molecular nitrogen could be incorporated into organic compounds to afford various heterocyclic compounds. Furthermore, novel titanium-catalyzed nitrogenation procedure was developed. That is, a THF solution of TiCl 4 or Ti(O i Pr) 4 , and an excess amount of Li and TMSCl was stirred under nitrogen (1 atm) at room temperature overnight and to this solution was added phthalic anhydride. The whole solution was refluxed overnight to afford a phthalimide in over 100 % yield. Using the stoichiometric conditions of the novel nitrogenation, various indole, pyrrole, pyrrolizine, indolizine derivatives and lactams were obtained in good to moderate yields after usual workup. Although the structure of the titanium-nitrogen complex has not been determined yet, the complex is thought to be a mixture of N(TMS) 3 , TiX 2 N(TMS) 2 and XTi=NTMS. Nitrogen in air could be directly fixed using this method, and the natural products, such as monomoline I, lycopodine and pumiliotoxin C, could be synthesized from nitrogen in air as a nitrogen source. CONTENTS 1. Introduction 2. Synthesis of Nitrogen Heterocycles Using Titanium Isocyanate Complex and Palladium Complex

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“…The cyclization precursor was in hand, we examined cyclic acylpalladation trapping by O-enolate to obtain 3. [5][6][7][8][9] As shown in Table 1, the choice of the base and solvent was very important. We found that AcONa as a base in DMF at 50 o C furnished desired 5-O-endo cyclized product 3 in 57% yield.…”

mentioning

confidence: 99%

Synthesis of legioliulin, a fluorescent isocoumarin compound, isolated from Legionella dumoffii using cyclic acylpalladation and Heck reaction

Asai

Hattori

Makabe

2016

Tetrahedron Letters

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Incorporation of molecular nitrogen into organic compounds

Cited by 31 publications

References 7 publications

Cyclic Enolates of Ni and Pd: Equilibrium between C‐ and O‐Bound Tautomers and Reactivity Studies

Cyclic Enolates of Ni and Pd: Equilibrium between C‐ and O‐Bound Tautomers and Reactivity Studies

Synthesis of Nitrogen Heterocycles Utilizing Molecular Nitrogen as a Nitrogen Source and Attempt to Use Air Instead of Nitrogen Gas

Synthesis of legioliulin, a fluorescent isocoumarin compound, isolated from Legionella dumoffii using cyclic acylpalladation and Heck reaction

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