Synthesis of crownophanes possessing three pyridine rings

Inokuma, Seiichi; Yatsuzuka, Takayaki; Ohtsuki, Shinji; Hino, Shota; Nishimura, Jun

doi:10.1016/j.tet.2007.03.099

Cited by 7 publications

(3 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This observation led us to the hypothesis that Ag + might play an active role and possibly promotes the σ Η -adduct formation. The well-known coordination properties of Ag + for a sp 2 nitrogen atom of (di)azines support this . Similarly, in the case of the 1,3-dinitrobenzene ( 2 ) substrate an oxygen atom of a nitro group can be involved in such a coordination.…”

Section: Resultsmentioning

confidence: 76%

ONSH: Optimization of Oxidative Alkylamination Reactions through Study of the Reaction Mechanism

Verbeeck

Herrebout²,

Gulevskaya

et al. 2010

J. Org. Chem.

View full text Add to dashboard Cite

Oxidative alkylamination of electron-deficient (hetero)aromatic compounds, via the nucleophilic substitution of hydrogen, is a methodology that has made significant progress since the introduction of AgPy(2)MnO(4) as oxidant. This oxidant generally gives good conversions and yields, whereas the use of KMnO(4) only sometimes works equally well. In order to rationalize this, the reaction mechanism of oxidative alkylamination has been studied. 3-Nitropyridine (1), 1,3-dinitrobenzene (2), and quinazoline (3) were chosen as model substrates and n-butylamine and pyrrolidine as model alkylamines. The rate-limiting step of the mechanism for these substrate/alkylamine combinations was determined. With the use of (1)H NMR spectroscopy thermodynamic properties of sigma(Eta)-adduct formation were deduced and the effect of additives on the adduct formation was investigated. The fundamental insights resulting from these studies led to the identification of a cheap additive (tetrabutylammonium chloride), which in combination with the standard and cheap oxidant KMnO(4) generally gave excellent yields, similar to the ones previously obtained with more expensive AgPy(2)MnO(4).

show abstract

Section: Resultsmentioning

confidence: 76%

ONSH: Optimization of Oxidative Alkylamination Reactions through Study of the Reaction Mechanism

Verbeeck

Herrebout²,

Gulevskaya

et al. 2010

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…The di(vinylpyridine) 65 was subjected to Pyrex-filtered irradiation which resulted in formation of the desired product 66 (Scheme ). This compound and a related pyridinocrownophane showed a particularly high affinity to silver ions. Various other crown ethers were assembled by the Nishimura group employing related methods. − …”

Section: Direct Excitation and Sensitizationmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

View full text Add to dashboard Cite

The [2 + 2] photocycloaddition is undisputedly the most important and most frequently used photochemical reaction. In this review, it is attempted to cover all recent aspects of [2 + 2] photocycloaddition chemistry with an emphasis on synthetically relevant, regio-, and stereoselective reactions. The review aims to comprehensively discuss relevant work, which was done in the field in the last 20 years (i.e., from 1995 to 2015). Organization of the data follows a subdivision according to mechanism and substrate classes. Cu(I) and PET (photoinduced electron transfer) catalysis are treated separately in sections 2 and 4, whereas the vast majority of photocycloaddition reactions which occur by direct excitation or sensitization are divided within section 3 into individual subsections according to the photochemically excited olefin.

show abstract

“…Following this work, the authors also accomplished the synthesis of crownophanes 124 possessing three pyridine rings via the same photocycloaddition from 123, albeit in low efficiency (only 15% yield). 68 Apart from regular organic compounds, organometallic complexes can also undergo the [2+2] cycloaddition efficiently (Scheme 33). In 2004, Erker et al reported an interesting ansa-metallocene framework 126 through the intramolecular [2+2] photocycloaddition of a bis(2-alkenylindenyl)zirconium complex 125.…”

Section: Scheme 31 Olefin Cycloaddition In the Total Synthesis Of Rhododaurichromanic Acidsmentioning

confidence: 99%

Recent Synthetic Applications of Catalyst-Free Photochemistry

Liu¹,

Li²

2017

Synlett

View full text Add to dashboard Cite

Catalyst-free photochemistry provides numerous opportunities toward sustainable synthesis because catalyst separation can usually be avoided, which is consistent with green chemistry principles. Complementary to the well-reviewed photoredox chemistry, this review specifically summarizes the synthetic applications of photochemistry without external catalysts reported since 2000. The selected examples include both natural product synthesis and new methodology development. This review is arranged based on the type of chromophore. It is our hope that this review will inspire more synthetic chemists to embrace photochemistry into their research plans.1 Introduction2 Photochemistry of Olefins2.1 [2+2] Cycloaddition of Enones and Olefins2.2 Cycloaddition of Olefins without Carbonyl Groups2.3 Z/E Isomerization2.4 Cyclization2.5 Others3 Photochemistry of C=O3.1 The Paternò–Büchi Reaction3.2 The Yang Photoenolization3.3 The Norrish Type I Reaction3.4 The Norrish Type II Reaction3.5 Others4 Photochemistry of Nitrogen-Containing Functional Groups5 Photochemistry of Halogen-Containing Compounds6 Conclusion and Outlook

show abstract

Synthesis of crownophanes possessing three pyridine rings

Cited by 7 publications

References 31 publications

ONSH: Optimization of Oxidative Alkylamination Reactions through Study of the Reaction Mechanism

ONSH: Optimization of Oxidative Alkylamination Reactions through Study of the Reaction Mechanism

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Synthetic Applications of Catalyst-Free Photochemistry

Contact Info

Product

Resources

About

Synthesis of crownophanes possessing three pyridine rings

Cited by 7 publications

References 31 publications

ONSH: Optimization of Oxidative Alkylamination Reactions through Study of the Reaction Mechanism

ONSH: Optimization of Oxidative Alkylamination Reactions through Study of the Reaction Mechanism

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Synthetic Applications of Catalyst-Free Photochemistry

Contact Info

Product

Resources

About

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions