Novel synthesis of methine dyes absorbing in the near-infrared region

Palladium‐Catalyzed One‐Pot Four‐Component Synthesis of β‐Cyano‐α,β‐unsaturated Ketones Using Calcium Carbide as an Acetylene Source and Potassium Hexacyanoferrate(II) as an Eco‐Friendly Cyanide Source

“…At the same time, the substances containing β‐cyano‐α,β‐unsaturated ketone moieties also have great potential application value . Figure shows two structures which can separately be used as a calciumchannel blocker (treating hypertension, cerebral artery occlusion and Alzheimer's disease) and a new type of near‐infrared dye …”

“…[1][2][3] At the same time, the substances containing β-cyano-α,β-unsaturated ketone moieties also have great potential application value. [7] In the past years, a few synthetic methods for βcyano-α,β-unsaturated ketones were reported (Scheme 1), which included i) the reactions of (phenacylidene)triphenylphosphorane with benzoyl cyanide; [8] ii) the palladium-catalyzed reactions of arylacetylenes with aroyl cyanides; [9] iii) the nickel-catalyzed conjugate addition of trimethylsilyl cyanide to ynones; [10] and iv) the reactions of cyclic bromo imidates with triethylamine. [7] In the past years, a few synthetic methods for βcyano-α,β-unsaturated ketones were reported (Scheme 1), which included i) the reactions of (phenacylidene)triphenylphosphorane with benzoyl cyanide; [8] ii) the palladium-catalyzed reactions of arylacetylenes with aroyl cyanides; [9] iii) the nickel-catalyzed conjugate addition of trimethylsilyl cyanide to ynones; [10] and iv) the reactions of cyclic bromo imidates with triethylamine.…”

“…[4] Figure 1 shows two structures which can separately be used as a calciumchannel blocker (treating hypertension, cerebral artery occlusion [5] and Alzheimer's disease [6] ) and a new type of near-infrared dye. [7] In the past years, a few synthetic methods for βcyano-α,β-unsaturated ketones were reported (Scheme 1), which included i) the reactions of (phenacylidene)triphenylphosphorane with benzoyl cyanide; [8] ii) the palladium-catalyzed reactions of arylacetylenes with aroyl cyanides; [9] iii) the nickel-catalyzed conjugate addition of trimethylsilyl cyanide to ynones; [10] and iv) the reactions of cyclic bromo imidates with triethylamine. [11] However, there are a number of problems with these synthetic methods, such as environment-unfriendly reagents, limited sources of raw materials, limited functional group compatibility, lengthy synthetic steps and unsafe cyanide sources, etc.…”

Development of Fluorescent 2-Pyrone Derivatives Using Ketene Dithioacetals for Organic EL Devices

“…This research finding triggered the development of fluorescence 2H-pyrone derivatives. [20][21][22][23][24][25][26] Scheme 1 The arrangement of suitable chromophores and auxochromes within the molecules both in the solution and solid states is necessary to confer fluorescent properties to a compound. In this respect, heterocycles synthesized using ketene dithioacetals have good substituents show fluorescence, due to ketene dithioacetals having strong electro-donating groups such as a methylsulfanyl group and strong electro-withdrawing groups such as cyano and ester groups.…”