The synthesis of a linear tröger's base derived from naphthalene: 7H‐15H‐6,14‐methanodinaphtho[2,3‐b:2′,3′‐f][1,5]diazocine

Pardo, Carmen; Pirat, Céline; Elguero, José

doi:10.1002/jhet.5570440611

Cited by 6 publications

(3 citation statements)

References 13 publications

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“…The only example appearing in the literature is the cyclization of methyl 2-aminonicotinate, which resulted in the cyclic dilactams with low yield. 33 Considering these aspects, a series of aromatic/heteroaromatic compounds bearing adjacent amino and ester groups were either purchased or synthesized to investigate the influence of these two factors. The results are shown in Table 1, column 2.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation

et al. 2014

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A newly developed reductive ring closure methodology to heteroacenes bearing a dihydropyrrolo[3,2-b]pyrrole core was systematically studied for its scope and limitation. The methodology involves (i) the cyclization of an o-aminobenzoic acid ester derivative to give an eight-membered cyclic dilactam, and (ii) the conversion of the dilactams into the corresponding diimidoyl chloride, which undergoes (iii) reductive ring closure to install the dihydropyrrolo[3,2-b]pyrrole core. The first step of the methodology plays the key role due to its substrate limitation, which suffers from the competition of oligomerization and hydrolysis. All the dilactams could successfully convert to the corresponding diimidoyl chlorides, most of which succeeded to give the dihydropyrrolo[3,2-b]pyrrole core. The influence of the substituents and the elongation of conjugated length on the photophysical properties of the obtained heteroacenes were then investigated systematically using UV-vis spectroscopy and cyclic voltammetry. It was found that chlorination and fluorination had quite a different effect on the photophysical properties of the heteroacene, and the ring fusing pattern also had a drastic influence on the band gap of the heteroacene. The successful preparation of a series of heteroacenes bearing a dihydropyrrolo[3,2-b]pyrrole core would provide a wide variety of candidates for further fabrication of organic field-effect transistor devices.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…On the other hand, whether the cyclization could be expanded to other heterocycles is still a question to be answered. The only example appearing in the literature is the cyclization of methyl 2-aminonicotinate, which resulted in the cyclic dilactams with low yield …”

Section: Resultsmentioning

confidence: 99%

Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation

et al. 2014

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“…Thus, a naphthalene analog (AE)-8 of Trçgers base is inaccessible via the condensation of naphthalen-2-amine with formaldehyde due to lower reactivity of position 3 vs. position 1. However, (AE)-8 was successfully synthesized in three steps by sequential build-up of the central methanodiazocine moiety starting from the methyl ester of 3-aminonaphthalene-2-carboxylic acid (Scheme 3) [36].…”

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confidence: 99%

Recent Developments in Synthetic Chemistry, Chiral Separations, and Applications of Tröger's Base Analogues

Sergeyev

2009

Helvetica Chimica Acta

132

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Trçgers base is a well-known chiral molecule with a few unusual structural features. The chemistry of Trçgers base analogues has been greatly developed over the last 20 years, and numerous interesting applications in supramolecular chemistry and in molecular recognition have emerged. This Review gives a short overview of the chemistry of Trçgers base and its analogues, with particular focus on recent achievements in synthesis, enantiomer separations, and applications.

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ChemInform Abstract: The Synthesis of a Linear Troeger′s Base Derived from Naphthalene: 7H‐15H‐6,14‐Methanodinaphtho[2,3‐b:2′,3′‐f][1,5]diazocine.

2008

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The synthesis of a linear tröger's base derived from naphthalene: 7H‐15H‐6,14‐methanodinaphtho[2,3‐b:2′,3′‐f][1,5]diazocine

Abstract: The title compound 3 was prepared in four steps from commercial 3‐amino‐2‐naphthoic acid in an overall 75 % yield. Attempts to use the same approach in the case of 2‐aminonicotinic acid methyl ester failed. All the compounds were characterized by NMR.

Cited by 6 publications

References 13 publications

Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation

Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation

Recent Developments in Synthetic Chemistry, Chiral Separations, and Applications of Tröger's Base Analogues

ChemInform Abstract: The Synthesis of a Linear Troeger′s Base Derived from Naphthalene: 7H‐15H‐6,14‐Methanodinaphtho[2,3‐b:2′,3′‐f][1,5]diazocine.

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