Zur Photolyse 3‐arylsubstituierter 3H‐Pyrazole

Schrader, Lutz

doi:10.1002/cber.19711040333

Cited by 32 publications

(5 citation statements)

References 13 publications

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“…The minor component (5%) present in the photolysis mixture derived from 19 was identified as l-phenyl-2-methyl-3-allylindene (21) on the basis of its characteristic spectral data: IR (neat) 3.32,3.45,6.12, 6.24, 6.71, 6.90. 9.75, 10.05, 10.90, 12.85, 13.30, 13.65, 14.35 µ ; UV (95% ethanol) 263 nm U 6900), 220 (17 800); NMR (CDC13,100 MHz) r 8.16 (s, 3 H), 6.68 (d, 2 H, J = 5.5 Hz), 5.72 (s, 1 ), 4.80-5.24 (m, 2 H), 3.82-4.28 (m, 1 ), 2.64-3.10 (m, 9 H); m/e 246 (M+), 206,205 (base), 108, 77. The structure of this material was further verified by comparison with an independently synthesized sample.…”

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confidence: 99%

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Photochemical transformations of small ring compounds. 95. The problem of regioselectivity in the photochemical ring-opening reaction of 3-phenyl- and 3-vinyl-substituted cyclopropenes to indenes and 1,3-cyclopentadienes

Padwa¹,

Blacklock²,

Getman³

et al. 1978

J. Org. Chem.

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confidence: 99%

“…After drying over magnesium sulfate, the solvent was removed under reduced pressure to give 0.76 g of a yellow oil. This material was purified by thick-layer chromatography to give 0.6 g (65%) of l-phenyl-2-methyl-3-allylindene (21) which was ide itical to the minor component obtained from the pho-tolysis of 19.…”

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confidence: 99%

Photochemical transformations of small ring compounds. 95. The problem of regioselectivity in the photochemical ring-opening reaction of 3-phenyl- and 3-vinyl-substituted cyclopropenes to indenes and 1,3-cyclopentadienes

Padwa¹,

Blacklock²,

Getman³

et al. 1978

J. Org. Chem.

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“…Gas chromatographic analysis and collection on column E at 180°g ave: 30 (retention time 3.5 min, 31 %), 31 (retention time 6 min, 64%), and an unidentified product (retention time 8 min, 15%).…”

Section: Methodsmentioning

confidence: 99%

“…Neither cyclopropenes nor indenes are formed. The products (28)(29)(30)(31) :, " 15% most easily rationalized through an abstraction-recombination mechanism. Presumably here we see the same kind of steric effect postulated previously to account for the increase in abstraction as the substitution of alkenes increases.…”

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confidence: 99%

Reactions of diphenylcarbene with alkenes, alkynes, and alkenynes

Baron¹,

Henrick²,

Jones³

1973

J. Am. Chem. Soc.

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Diphenylcarbene reacts with olefins by both addition and abstraction. The partitioning of the reaction between these paths is determined largely by steric factors. The stereochemistry of addition has been determined in a system favorable to triplet reaction. With acetylenes, both addition and abstraction occur, but the intermediate generated by addition is often diverted from a path leading to the usual cyclopropene and gives indene instead.

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“…Indolepyridine is the main structural element of many natural products [8], among which there are antitumor [9] and antidiabetic [10] agents. On this basis compounds 4a-d and 5a-c are of interest in themselves as possible biologically active substances.…”

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Derivatives of indole. 143.* synthesis of photochromic derivatives of 2-arylindoles

Gogrichiani

Katsadze

Gavtadze

et al. 2004

Chem Heterocycl Compd

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New derivatives of 2-arylindoles containing (4-pyridyl)alkyl substituents at various positions of the pyrrole ring were synthesized. They react with 2,3-dimethoxycarbonylspirofluorenylcyclopropene with the formation of light-sensitive systems belonging to the photochromic dihydroindolizine class.Photochromic dihydroindolizines form a rich and varied class of light-sensitive compounds [2,3]. Among the multitude of photochromic materials they are distinguished by high their efficiency, their cheapness, and their accessibility. This forms the basis of their prospective use in optical lenses, the recording and storage of data [4], and dental materials [5].In the present work we describe the synthesis and photochromic characteristics of novel 2-arylindole systems containing a dihydroindolizine ring. It seemed to us important to couple the qualities of 2-arylindoles, which form the fundamental unit in many biologically active systems [6,7], and those of photochromic molecules. Model systems of such a type are promising for use as marker molecules in the study of biological processes.A standard and effective method for the production of photochromic dihydroindolizines is the addition of electron-excessive N-heterocyclic bases to spirocyclopropene. Such bases for us were the 1-and 3-(4-pyridyl)alkyl-substituted 2-arylindoles 4a-d and 5a-c that we had synthesized.Indolepyridine is the main structural element of many natural products [8], among which there are antitumor [9] and antidiabetic [10] agents. On this basis compounds 4a-d and 5a-c are of interest in themselves as possible biologically active substances.The initial bases 4a-d and 5a-c were produced by alkylation of the respective 2-arylindoles, obtained by the Fischer method [11] (Scheme 1).The 1-(4-pyridylmethyl)-2-arylindoles 4a-d were obtained by N-alkylation of 2-arylindoles (1) with 4-(chloromethyl)pyridine in the 50% aqueous potassium hydroxide-benzene two-phase system in the presence of tetrabutylammonium bromide.It is known that 4-vinylpyridine in an acidic medium alkylates the indole ring at position 3 [12]. In our case too by boiling 2-arylindoles 1a-c with 4-vinylpyridine 3 we obtained the corresponding 3-[2-(4-pyridyl)ethyl] derivatives 5a-c.

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Zur Photolyse 3‐arylsubstituierter 3H‐Pyrazole

Cited by 32 publications

References 13 publications

Photochemical transformations of small ring compounds. 95. The problem of regioselectivity in the photochemical ring-opening reaction of 3-phenyl- and 3-vinyl-substituted cyclopropenes to indenes and 1,3-cyclopentadienes

Photochemical transformations of small ring compounds. 95. The problem of regioselectivity in the photochemical ring-opening reaction of 3-phenyl- and 3-vinyl-substituted cyclopropenes to indenes and 1,3-cyclopentadienes

Reactions of diphenylcarbene with alkenes, alkynes, and alkenynes

Derivatives of indole. 143.* synthesis of photochromic derivatives of 2-arylindoles

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