Rearrangements Involving alkoxycarbonyl group migration between nitrogen and oxygen.III. Reactions of modified isoquinoline Reissert compounds with aldehydes

Rozwadowska, Maria D.

doi:10.1139/v77-028

Cited by 12 publications

(4 citation statements)

References 14 publications

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“…This condensation process can be carried out with phenyllithium in ether-dioxane, 8,12(a-c) with sodium hydride in dimethylformamide 12(d,e) or under phase transfer conditions with 50% sodium hydroxide/acetonitrile; in the latter case, mixtures of the ester (2) and alcohol (3) or one of them exclusively result, depending on the reaction time and temperature. 13,14 The anions react with alkyl halides, forming 1-alkyl derivatives 4, whose basic hydrolysis affords 1-alkylisoquinolines (5) through rearomatization (Scheme 2). 8,12(d),15,16 An intramolecular rearrangement in the absence of an electrophile converts the Reissert anion into ketone 6.…”

Section: Reissert Compoundsmentioning

confidence: 99%

“…Hydrolysis of the esters affords the corresponding secondary alcohols 3 . This condensation process can be carried out with phenyllithium in ether‐dioxane,8, 12(a–c) with sodium hydride in dimethylformamide12(d,e) or under phase transfer conditions with 50% sodium hydroxide/acetonitrile; in the latter case, mixtures of the ester ( 2 ) and alcohol ( 3 ) or one of them exclusively result, depending on the reaction time and temperature 13, 14…”

Section: Introductionmentioning

confidence: 99%

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Heterocyclic monomers via reissert chemistry

Gibson

Rasco

Niu

2011

J. Polym. Sci. A Polym. Chem.

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An AA bisphenolic monomer (13), an AB activated fluoro‐phenolic monomer (14), and an AB2 alcohol‐diester monomer precursor (17), all based on the isoquinoline nucleus, were prepared using Reissert compound chemistry. Additionally, model reactions established the efficiency of condensation of isoquinoline Reissert compounds with dihaloalkanes, providing evidence of the potential of this reaction to produce high molecular weight polymers, which was subsequently realized. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

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Section: Reissert Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Heterocyclic monomers via reissert chemistry

Gibson

Rasco

Niu

2011

J. Polym. Sci. A Polym. Chem.

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“…However, it has been shown that the base/solvent combination and the reaction time and temperature dictate which product will be obtained. Shorter reaction times and lower temperatures favor formation of the ester 8…”

Section: Introductionmentioning

confidence: 99%

Synthesis of heterocyclic monomers via Reissert chemistry

Gibson

Brumfield

Grisle

et al. 2010

J. Polym. Sci. A Polym. Chem.

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The chemistry of Reissert compounds has been used to synthesize activated difluorotetraketone monomers containing two coupled isoquinolyl moieties, linked at either the 1,1 0 -or 4,4 0 -positions. These monomers offer routes to novel families of poly(heteroarylene ether)s. New 4,4 0 -coupled bis(Reissert compound) 9 containing 4,4 0 -diketo moieties failed to afford the desired difluorotetraketo monomer upon attempted rearrangement. However, analogous bis(Reissert compound) 19 containing 4,4 0 -dibenzyl units did so, via aldehyde condensation, hydrolysis of the intermediate ester and oxidation of the four benzylic moieties to keto groups; thus the novel difluorotetraketone monomer 10 was prepared. Novel bis(Reissert compound)s 24, 28, and 35 were synthesized from diacid chlorides and 4-(pfluorobenzyl)isoquinoline. Rearrangement of 24 to the diketone 29, followed by oxidation of the 4-benzyl moieties resulted in difluorotetraketone monomer 30 containing a 1,1 0 -linked bisisoquinoline. The 1,1 0 -linked bis(isoquinolylfluorodiketo) monomer 38, isomeric with 10, was prepared from 4-(p-fluorobenzyl) Reissert compound 36 by condensation with terephthaldehyde, ester hydrolysis to diol 37, and oxidation. In the course of this effort, a number of new isoquinoline Reissert compounds were synthesized as model systems. V C 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: [3856][3857][3858][3859][3860][3861][3862][3863][3864][3865][3866][3867] 2010

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“…At the same time the pyridine -cupric sulfate test (18) for the detection of isocyanates was negative.…”

mentioning

confidence: 95%