- Eco-friendly organocatalyst- And reagent-controlled selective construction of diverse and multifunctionalized 2-hydroxybenzophenone frameworks for potent UV-A/B filters by cascade benzannulation
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The organocatalyst- and reagent-controlled highly selective synthesis of diversely functionalized novel 2-hydroxybenzophenone frameworks, such as 2-hydroxy-3′-formylbenzophenones, 7-(2′-hydroxybenzoyl)-2-naphthaldehydes, and 2-hydroxybenzophenones, under green conditions, for the development of potent UV-A/B filters is described. The organocatalyzed benzannulation reactions proceed individually via [3 + 3] cycloaddition for the synthesis of 2-hydroxy-3′-formylbenzophenones and [4 + 2] cycloaddition for 2-hydroxybenzophenones. With this methodology, an unprecedented double benzannulation allows one-pot construction of diverse 7-(2′-hydroxybenzoyl)-2-naphthaldehydes via [3 + 3 + 4] cycloaddition. This protocol features a broad substrate scope, high functional-group tolerance, and operational simplicity in an environmentally benign green solvent. The synthesized compounds are successfully utilized for further transformations and well characterized as potent UV-A/B filters.
- Akhtar, Muhammad Saeed,Inductivo Tamargo, Ramuel John,Kim, Sung Hong,Lee, Yong Rok,Thombal, Raju S.,Yang, Won-Guen
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supporting information
p. 4523 - 4531
(2020/08/10)
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- Operationally Simple and Selective One-Pot Synthesis of Hydroxyphenones: A Facile Access to SNARF Dyes
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High selectivity is observed during a Friedel-Crafts acylation/demethylation cascade. In contrast to this cascade, oxygen-containing acylating reagents do not undergo the demethylation step. By the methodology elaborated here, an access is provided to important intermediates for the total synthesis of seminaphthorhodafluor (SNARF) dyes.
- Richter, Celin,Ernsting, Nikolaus P.,Mahrwald, Rainer
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p. 1217 - 1225
(2016/05/11)
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- Synthesis of 2-acylphenol and flavene derivatives from the ruthenium-catalyzed oxidative c-h acylation of phenols with aldehydes
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The cationic ruthenium hydride complex [(C6H6)(PCy3)(CO)RuH]+BF4- has been found to be an effective catalyst for the oxidative C-H coupling reaction of phenols with aldehydes to give 2-acylphenol compounds. The coupling of phenols with α,β-unsaturated aldehydes selectively gives the flavene derivatives. The catalytic method mediates direct oxidative C-H coupling of phenol and aldehyde substrates without using any metal oxidants or forming wasteful byproducts. A cationic ruthenium hydride complex catalyzes the oxidative C-H coupling of phenols with aldehydes to form 2-acylphenol and flavene derivatives.
- Lee, Hanbin,Yi, Chae S.
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supporting information
p. 1899 - 1904
(2015/03/18)
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- Cosmetic compositions
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Suggested is a cosmetic compositions comprising (a) a crosspolymer obtained from copolymerisation of at least two different polyols and at least one dicarboxylic acid and (b) at least one fragrance.
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- A composition for lightening skin and hair
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Suggested is a composition comprising (a) sclareolide and (b1) at least one tyrosinase inhibitor; and/or (b2) at least one sun protection factor; and/or (b3) at least one anti-oxidants; and/or (b4) at least one anti-inflammatory agent; and/or (b5) at least one desquamating agent.
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- A concise approach to the preparation of 2-hydroxydiarylketones by an intramolecular acyl radical ipso substitution
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Substituted 2-hydroxydiarylketones have been simply prepared using an intramolecular acyl radical [1,6] ipso substitution reaction. (C) 2000 Elsevier Science Ltd.
- Motherwell,Vazquez
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p. 9667 - 9671
(2007/10/03)
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- Light-stable screening cosmetic composition containing bixin combined with a lipid-soluble UV filter and its use for protecting the human epidermis against ultra-violet radiation
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The invention relates to a light-stable cosmetic composition for protecting the human epidermis against UV radiation, containing at least 0.0025% by weight of bixin combined with at least 1% by weight of one or more lipid-soluble agents screening UV radiation, chosen from 3-benzylidene-dl-camphor, its derivatives and benzophenone derivatives, in a cosmetically acceptable vehicle comprising at least one fatty phase. The bixin takes the form of an oily extract of annatto containing at least 0.1% by weight of bixin.
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- BORON TRICHLORIDE CATALYZED ORTHO CARBONYLATION OF PHENOLS: SYNTHESIS OF 2-HYDROXY-ARYL-CARBOXYAMIDES AND -KETONES.
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In the presence of equimolar quantity of BCl3, phenols 1 react with isocyanates and acyl chlorides to give, usually with good-excellent yields, 2-hydroxy-aryl-carboxy-amides 2 and 2-hydroxy-aryl-ketones 3 respectively.A distinctive behaviour of BCl3 in comparison with other Lewis acids is observed.
- Piccolo, Oreste,Filippini, Lucio,Tinucci, Laura,Valoti, Ermanno,Citterio, Attilio
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p. 885 - 892
(2007/10/02)
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- Method of treating inflammation
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A method of treating inflammation and inhibiting prostaglandin synthesis employing 2-hydroxybenzophenone and substituted 2-hydroxybenzophenones.
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- Infrared study of polysubstitution effects in benzophenones and acetophenones: contribution of inter and intracycle interaction mechanisms
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The carbonyl stretching frequencies of substituted 2-Me, 2,6-diMe, 2-MeO benzophenones and 2-Me, 2-MeO acetophenones have been measured in diluted CCl4 solutions.Two interaction mechanisms are observed.In X, Y substituted benzophenones with X on the same cycle as the ortho group and Y on the other cycle, it is shown that for X=Y, the effect of Y is greater than that of X except for very strong electron-releasing substituents.In this last case, the observed enhancement is attributed to the joint effects of intercycle interactions excercised on X and Y and of intracycle interaction on X.These results are corroborated by the study of substituted acetophenones in which only the intracycle mechanism can play a role.
- Goethals, G.,Nadio, L.,Uzan, R.
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p. 199 - 204
(2007/10/02)
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