Synthesis of Novel Functionalized Bi- and Oligopyridines

Sielemann, Dirk; Keuper, Ralf; Risch, Nikolaus

doi:10.1002/(sici)1099-0690(200002)2000:3<543::aid-ejoc543>3.0.co;2-v

Cited by 18 publications

(11 citation statements)

References 44 publications

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“…Risch and co-workers developed annelation protocols where 1,3-cyclohexanedione is converted, through Mannich reactions, into functionalized oligopyridines . An example is provided in the synthesis of the unsymmetrically fused qtpy-type ligand 7 through Michael addition condensation reactions in four steps (Figure ).…”

Section: Synthetic Methodsmentioning

confidence: 99%

Quaterpyridines as Scaffolds for Functional Metallosupramolecular Materials

et al. 2016

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Quaterpyridine (qtpy) ligands have found significant applications as N-heterocyclic scaffolds in self-assembly processes, in particular the formation of various metallosupramolecular architectures, limited, however, by difficulties in their synthesis. Recent progress in the preparative organic and organometallic chemistry of polypyridines has resulted in the elimination of the most serious drawbacks concerning qtpy synthesis, consequently giving rise to a renewed interest in this class of compounds. Herein, we endeavor to define the essential aspects of quaterpyridine chemistry and provide the reader with a perspective on the ways in which this field has begun to flourish.

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Section: Synthetic Methodsmentioning

confidence: 99%

Quaterpyridines as Scaffolds for Functional Metallosupramolecular Materials

et al. 2016

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“…Bisiminium salts 24 − 33 have been employed successfully in a highly efficient 2-fold domino sequence with 4 equiv of 1 and NH 4 OAc, as a source of ammonia, to give bis(U-terpyridines) 34 − 43 in good yields (Scheme 2, Table ). The proposed mechanism for the selective formation of U-terpyridines has already been discussed elsewhere 11l. When optimized reaction conditions are used,11l the formation of the undesired bis(S-terpyridine) in small amounts has only been observed in a single case ( 43 , 5%).…”

Section: Resultsmentioning

confidence: 95%

“…The proposed mechanism for the selective formation of U-terpyridines has already been discussed elsewhere 11l. When optimized reaction conditions are used,11l the formation of the undesired bis(S-terpyridine) in small amounts has only been observed in a single case ( 43 , 5%). Our results show that the length and the substitution pattern of the linker can be tuned easily depending on the structure of the iminium compound.…”

Section: Resultsmentioning

confidence: 95%

“…Domino reactions offer many advantages compared to traditional syntheses, such as the minimization of waste and the reduced consumption of solvents, reagents, adsorbents, and energy. As shown earlier, the reaction of a ternary iminium salt 2 and two equivalents of 5,6,7,8-tetrahydroquinolinone 1 in the presence of ammonium acetate, as a source of ammonia, under appropriate conditions leads to the formation of rigid U-shaped substituted terpyridines 3 , selectively, whereas the S-shaped isomer is isolated in small amounts in very few cases (Scheme 1) 11l …”

Section: Introductionmentioning

confidence: 84%

“…The potential importance of the fields of metallopolymers and novel molecular devices means that the development of novel and more flexible synthetic methods is an active area of research. Our studies in the field of ternary iminium salts have led to the development of highly efficient, one-pot, domino-type reactions yielding a wide range of substituted rigid pyridine derivatives, including bipyridines and terpyridines . Domino reactions offer many advantages compared to traditional syntheses, such as the minimization of waste and the reduced consumption of solvents, reagents, adsorbents, and energy.…”

Section: Introductionmentioning

confidence: 99%

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Oligo(U-terpyridines) and Their Ruthenium(II) Complexes: Synthesis and Structural Properties

2006

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A highly efficient domino reaction starting from tetrahydroquinolinone and a series of bisiminium salts provides the corresponding bis(U-terpyridines). These ligands have been treated with [(tpy)RuCl3] to afford novel dinuclear complexes [(tpy)Ru(L)Ru(tpy)]4+. The protocol is also applied for the synthesis of a star-shaped tris(U-terpyridine) and the trinuclear complex [{(tpy)Ru}3(L)]6+. In view of potential applications in the fields of metallopolymers and molecular devices, the electronic spectra, as well as the electrochemical potentials of all the complexes have been obtained. According to these data, no significant intermetal interaction has been observed for the ruthenium complexes presented here.

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