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Mezheritskii, V. V.; Tyurin, R. V.; Minyaeva, L. G.

doi:10.1023/a:1012477718250

Cited by 8 publications

(12 citation statements)

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“…Formylation (Rieche method) afforded aldehyde 60 as the only product (yield 60%). 71 d. Naphthalene-based heterocyclic systems Formylation of peri-fused heterocyclic systems based on naphthalene was carried out in a series of studies. These systems are of interest because the heterocycle in these compounds serves as a special kind of substituent exerting a substantial effect on the degree of activation of the naphthalene system with respect to the electrophilic substitution as well as on the orientation effects.…”

Section: Compoundmentioning

confidence: 99%

“…The electronic structure of 1,2,2,3-tetramethyl-2,3-dihydroperimidine ( 88) is more similar to that of 1,8-bis(dimethylamino)naphthalene (53) rather than to that of perimidines 69 and 70. Being in addition a weak base, compound 88 is readily formylated (Scheme 2) to give monoaldehydes 89 and 90 and dialdehydes 91 R = H (69,71,72), Me (70,73,74). and 92.…”

Section: Compoundmentioning

confidence: 99%

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Naphthaldehydes

Пожарский¹

2003

Russ. Chem. Rev.

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Data on methods for the preparation of naphthalde-Data on methods for the preparation of naphthaldehydes, their physicochemical properties, structural characteristics hydes, their physicochemical properties, structural characteristics and reactivities are generalised. Particular attention is given to and reactivities are generalised. Particular attention is given to procedures for formylation of naphthalenes and procedures for formylation of naphthalenes and peri peri-interactions -interactions involving the aldehyde group in the involving the aldehyde group in the a a-position. The bibliography -position. The bibliography includes 201 references includes 201 references. .

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Section: Compoundmentioning

confidence: 99%

Section: Compoundmentioning

confidence: 99%

Naphthaldehydes

Пожарский¹

2003

Russ. Chem. Rev.

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“…Therefore, its 1 H NMR spectrum cannot be regarded as informative. Structure X shown in Scheme 3 was postulated by analogy with more stable derivatives of the naphthalene series [8]. The presence of a ketoenol fragment in molecule X was confirmed by the ability of this compound to form difluoridoboron and copper chelates XII and XIII.…”

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confidence: 94%

Pyran derivatives peri-fused to acenaphthene and acenaphthylene

2011

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peri-Acyloxyacenaphthenyl bromomethyl ketones prepared by bromination of peri-acyloxyacenaphthenyl methyl ketones reacted with sodium methoxide to give 2-acyl-3-hydroxyacenaphtho[5,6-bc]pyran derivatives, while their reaction with piperidine afforded acenaphtho[5,6-bc]pyran-3-on. Heating of the latter in acetic anhydride produced 3-acetoxyacenaphtho[5,6-bc]pyran which was subjected to dehydrogenation to obtain a new heteroaromatic system.Compounds possessing pronounced antibacterial properties comparable with those of strong antibiotics were found among peri-fused pyran derivatives [1, 2]. peri-Fused bis-pyran systems like 1,6-and 1,8-dioxapyrenes exhibited unusual photobiological and genotoxic activity [3,4], readily formed charge-transfer complexes [5], and were used as building blocks for the synthesis of so-called organic metals [6]. We previously synthesized 2-acylnaphtho[1,8-bc]pyran-3-ones and coordination compounds based thereon, which showed strong yellow-orange fluorescence and were proposed as effective chemosensors and highly sensitive analytical reagents for qualitative and quantitative determination of heavy metals [7]. Naphtho[1,8-bc]-pyran-3-ones were obtained by bromination of periacyloxynaphthyl alkyl ketones at the side alkyl chain OH Ac I OAc Ac II Ac 2 O, NaOAc OBz Ac III PhCOCl, pyridine OAc COCH 2 Br VI 1,4-Dioxane · Br 2 OH Ac IV CuBr 2 , EtOAc-CHCl 3 , Δ Br CuBr 2 , EtOAc-CHCl 3 , Δ OBz COCH 2 Br V Scheme 1.

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“…In continuation of the research on the chemistry of peri-fused heterocycles [1][2][3] we report here on the synthesis of a new bis-peri-fused heteroaromatic cation isolated as salt with perchlorate anion as the counter-ion.…”

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confidence: 99%