A Convenient Synthesis of Functionalised 1‐Aryl‐1,3‐alkadiynes

Балова, Ирина А.; Sorokoumov, V. N.; Морозкина, С. Н.; Vinogradova, O. V.; Knight, David W.; Vasilevsky, S. F.

doi:10.1002/ejoc.200400688

Cited by 26 publications

(14 citation statements)

References 22 publications

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“…10. A diazotization of o (alka 1,3 diynyl) arylamines 1a-i was carried out with the use of proce dures A-F (Scheme 1), the experimental data are given in Table 1.…”

Section: Resultsmentioning

confidence: 99%

“…10 Since the cyclization of diacetylenic derivatives of arenediazo nium salts can serve as a one step pathway to 4 halo 3 ethynylcinnolines, the promising building blocks, in particular, for the synthesis of polyfused heterocycles, 11 we continued our efforts in this field. Earlier, we briefly reported that the result of diazotization of o (alka 1,3 diynyl)anilines greatly depends on the reaction conditions and the nature of substituents in the aromatic ring.…”

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confidence: 99%

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Studies on cyclization of o-(alka-1,3-diynyl)arenediazonium salts

et al. 2008

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The Richter reaction of o (alka 1,3 diynyl)arenediazonium salts, obtained by diazotiza tion of diacetylenic derivatives of anilines, leads to 3 alkynyl 4 chloro or 3 alkynyl 4 bromocinnolines and/or 3 alkynyl 4 hydroxycinnolines (the latter cyclize into furo[3,2 c] cinnolines under the reaction conditions). 3 Alkynyl 4 chlorocinnolines undergo solvolysis in methanol giving rise to 3 alkynyl 4 methoxycinnolines, the subsequent hydrolysis of which also gives furo[3,2 c]cinnolines. Effects of the nature of substituents in the aromatic ring and of the reaction conditions on the product composition and yields have been established. The reaction course has been studied by spectrophotometry.

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“…10. A diazotization of o (alka 1,3 diynyl) arylamines 1a-i was carried out with the use of proce dures A-F (Scheme 1), the experimental data are given in Table 1.…”

Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Studies on cyclization of o-(alka-1,3-diynyl)arenediazonium salts

et al. 2008

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“…Compounds 361 were then found to be useful precursors to terminal 1,3-diynes 54 [184][185][186] and unsymmetrically 1,4disubstituted 1,3-diynes 365 184,187 (Scheme 123). Again in 2003, 188 Negishi and coworkers carried out the Sonogashira-type monoalkynylation reaction of 1,1dichloro-1-alkenes 366 under experimental conditions significantly different from those used in the synthesis of compounds 361.…”

Section: Monoalkynylation Reactions Of 11-dihalogenated 1alkenes 31 Monoalkynylation Reactions Of 11-dichloro-1alkenes 182mentioning

confidence: 99%

“…Mesylation of 181 followed by nucleophilic substitution with potassium thioacetate gave thioacetate 182 in 81% yield, which by desilylation and subsequent mesylation of the resulting alcohol provided compound 183 in 87% yield. Finally, simultaneous slow addition of solutions of 183 and sodium methoxide in MeOH via a syringe pump into a large amount of MeOH at room temperature gave the enediyne 184 in 61% yield (Scheme 64).Compound 184 was then converted into isothiochromanone(186) in 58% yield by heating in benzene (2 mM solution) in the presence of 1,4-cyclohexadiene at 80 °C 110. As shown in Scheme 65, the reaction very likely involved the formation of intermediate 185 via the Bergman reaction 90.…”

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Development and applications of highly selective palladium-catalyzed monocoupling reactions of (cyclo)alkenes and 1,3-alkadienes bearing two or three electrophilic sites and bis(enol triflates) with terminal alkynes

et al. 2013

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The motivation for writing this review with 558 references, which covers the literature up to the end of September 2012, is to fill a part of this gap by illustrating highly selective Pd/Cu-catalyzed and Cu-free Pd-catalyzed monoalkynylation reactions of (cyclo)alkenes and 1,3-butadienes bearing two or three identical or different electrophilic sites and bis(enol triflates) with terminal alkynes. However, Pd-catalyzed selective monocoupling reactions of 1-alkynes with (hetero)aryl halides or pseudohalides with two identical or different electrophilic sites will not be covered. Moreover, Pd-catalyzed monocoupling reactions of 1-alkynes with non-conjugated diene systems bearing an electrophilic site on each carbon–carbon double bond have also been considered to be beyond the scope of this review.\ud \ud In addition to describing and commenting on the aforementioned monoalkynylation reactions of (cyclo)alkenes and 1,3-dienes with two or three identical or different electrophilic sites and bis(enol triflates), emphasis has been placed on the use of Pd-catalyzed monoalkynylations of (cyclo)alkenes and 1,3-butadienes bearing two or three identical or different electrophilic sites and bis(enol triflates) as key steps of the syntheses of core structures and models of enediyne antitumor antibiotics, pharmacologically active compounds, and bioactive naturally occurring compounds including insect sex pheromone components, and fungal and plant metabolites. Moreover, the review has been focused on the formation of disubstituted acetylenic derivatives by one-pot site-selective Pd-catalyzed consecutive alkynylation reactions of di(pseudo)halogenated olefinic substrates with two different terminal alkynes. Where appropriate, the reasons for the observed stereo-, site-, and/or chemoselectivities of the reported Sonogashira-type monoalkynylation reactions have been mentioned and discussed

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“…[7][8][9] The electronic absorption spectra of phenyldiacetylene (phda) derivatives and the effect of solvent on the posi tion and contours of spectral bands have been studied for several years at the Laboratory of Spectrochemistry (De partment of Chemistry, St. Petersburg State University). This work involved the experimental and quantum chemi cal study of the electronic absorption spectra of solu tions of diacetylene derivatives with the general formula H 2 N-Ar-C≡C-C≡C-R ( Fig.…”

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The structures and electronic absorption spectra of substituted phenyldiacetylenes: experimental and theoretical studies

et al. 2007

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The results of experimental and theoretical investigation of the electronic absorption spec tra of substituted phenyldiacethylenes are presented. The bands in the experimental spectra were assigned in detail using quantum chemical calculations of the electronic structures and spectra of the molecules. The influence of the interaction of the substituents on the spectral parameters of the systems under study was analyzed.

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A Convenient Synthesis of Functionalised 1‐Aryl‐1,3‐alkadiynes

Cited by 26 publications

References 22 publications

Studies on cyclization of o-(alka-1,3-diynyl)arenediazonium salts

Studies on cyclization of o-(alka-1,3-diynyl)arenediazonium salts

Development and applications of highly selective palladium-catalyzed monocoupling reactions of (cyclo)alkenes and 1,3-alkadienes bearing two or three electrophilic sites and bis(enol triflates) with terminal alkynes

The structures and electronic absorption spectra of substituted phenyldiacetylenes: experimental and theoretical studies

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