936916-80-2Relevant academic research and scientific papers
CoCl(PPh3)3 as Cyclotrimerization Catalyst for Functionalized Triynes under Mild Conditions
Jungk, Phillip,Fischer, Fabian,Thiel, Indre,Hapke, Marko
, p. 9781 - 9793 (2015)
The ubiquitary Co(I) complex CoCl(PPh3)3 was found to be a convenient catalyst for the [2 + 2 + 2] cycloaddition of functionalized triynes under mild reaction conditions and devoid of any additional additive, yielding the substituted
Synthesis of DNA-Intercalating 6H-Benzo[c]chromen-6-one Derivatives through a Strategic Combination of Garratt-Braverman and Minisci Acyloxylation Reactions
Bhattacharya, Prabuddha,Mandal, Santi M.,Basak, Amit
, p. 1439 - 1448 (2016)
A new strategy for the synthesis of 6H-benzo[c]chromen-6-ones through judicious use of Garratt-Braverman (GB) Cyclization and Minisci acyloxylation reactions in moderate to good yield is reported. The uniqueness of the GB reaction is exemplified in providing the required biaryl esters, which could be successfully converted into the target skeleton by means of Minisci reaction on the free carboxylates. Ethidium bromide displacement and UV-based assay on the final molecules established them as DNA intercalators with binding constants in the range of about 104. Synthesis of DNA-intercalating benzochromenones through a combination of Garratt-Braverman and Minisci acyloxylation reactions is described.
Shifting the Reactivity of Bis-propargyl Ethers from Garratt-Braverman Cyclization Mode to 1,5-H Shift Pathway to Yield 3,4-Disubstituted Furans: A Combined Experimental and Computational Study
Das, Joyee,Das, Eshani,Jana, Saibal,Addy, Partha Sarathi,Anoop, Anakuthil,Basak, Amit
, p. 450 - 457 (2016/01/25)
Aryl or vinyl substituted bis-propargyl ethers upon base treatment generally form phthalans via the Garratt-Braverman (GB) cyclization pathway. In a major departure from this usual route, several aryl/vinyl bis-propargyl ethers with one of the acetylenic
Intramolecular anionic Diels-Alder reactions of 1-aryl-4-oxahepta-1,6-diyne systems in DMSO
Kudoh, Takayuki,Mori, Tomoko,Shirahama, Mitsuhito,Yamada, Masashi,Ishikawa, Teruhiko,Saito, Seiki,Kobayashi, Hisayoshi
, p. 4939 - 4947 (2008/02/03)
Base-promoted cycloaddition reactions of 1-aryl- or 1-aryl-7-substituted-4- oxahepta-1,6-diyne systems in DMSO have proven to involve an anionic intramolecular Diels-Alder process taking place even at room temperature in spite of the reaction suffering from temporary disruption of aromaticity. Although initially formed α-arylallenide anion can be protonated by DMSO, it can be back to the allenide anion probably because of a small acidity difference between α-arylallene and DMSO. The α-arylallenide anion in combination with the α-aryl substituent can constitute an anionic diene structure that undergoes the intramolecular Diels-Alder reaction involving the C(6)-yne part, a very fast process probably because of the increased HOMO-1 level of the anionic diene, as shown by DFT calculations. Diversified substituted naphthalenes, benzofurans, phenanthrenes, and quinolines, including biaryl architectures, are available from 4-oxahepta-1,6-diynes in a highly expeditious way.
