- The cooperative effect of Lewis pairs in the Friedel-Crafts hydroxyalkylation reaction: A simple and effective route for the synthesis of (±)-carbinoxamine
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An efficient C-C bond formation strategy between aromatic/heteroaromatic π-nucleophiles and Lewis acid activated aldehydes is described. This aromatic electrophilic substitution reaction of arenes or heteroarenes is facilitated by Lewis acid AlBr3. Aromatic rings with electron donating substituents are excellent nucleophilic counterparts in this reaction, generating carbinols in excellent yields (61-94%). The formation of triarylmethanes is also witnessed in the case of certain reactive aldehydes and aromatic π-nucleophiles through reactive carbocation formation. The formation of triarylmethane is reduced to a greater extent via retardation of the second π-nucleophile addition through a Lewis base, for example, pyridine, coordination with an aluminium alkoxide intermediate. Various aliphatic aldehydes also underwent Friedel-Crafts type hydroxyalkylation and generated the expected carbinols in moderate yields (41-53%) in the presence of AlBr3. This protocol has been successfully applied to the synthesize of the (±)-carbinoxamine, a therapeutically important histamine H1 antagonist, in a one-pot manner.
- Harikrishnan, Adhikesavan,Sanjeevi, Jayakumar,Ramanathan, Chinnasamy Ramaraj
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p. 3633 - 3647
(2015/03/30)
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- An effective system to synthesize hypolipidemic active α-asarone and related methoxylated (E)-arylalkenes
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Methoxylated (E)-arylalkenes (1a-1k) were prepared in two steps by an improved Grignard reaction comprising the reverse addition of alkylmagnesium bromide to benzaldehydes (2a-2k) in anhydrous ether and toluene into arylalkanols (3a-3k) in high yield, followed by dehydration with silica gel under microwave irradiation for 3-12 min, depending upon the substituents attached to the aromatic ring to afford hypolipidemic active α-asarone (1a) and related methoxylated (E)-arylalkenes (1b-1k).
- Sharma, Anuj,Joshi, Bhupendra P.,Sinha, Arun K.
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p. 2231 - 2235
(2007/10/03)
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- Feeding-deterrent activity of α-asarone isomers against some stored Coleoptera
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All isomers of α-asarone [(E)-4-prop-1-enyl-1,2,5-trimethoxybenzene] were tested for their feeding deterrent activity against adults of Sitophilus granarius and Tribolium confusum and larvae of Trogoderma granarium and Tribolium confusum. (E)-2-prop-1-eny
- Poplewski, Janusz,Lozowicka, Bozena,Dubis, Alina T.,Lachowska, Barbara,Winiecki, Zbigiew,Nawrot, Jan
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p. 560 - 564
(2007/10/03)
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- Synthesis and hypolipidemic and antiplatelet activities of α-asarone isomers in humans (in vitro), mice (in vivo), and rats (in vivo)
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A series of α-asarone isomers was synthesized and investigated for their hypolipidemic and antiplatelet activity. Considering the hypolipidemic activity in rats at a dose of 80 mg/kg/day, some isomers were more potent than clofibrate at 150 mg/kg. Compoun
- Poplawski,Lozowicka,Dubis,Lachowska,Witkowski,Siluk,Petrusewicz,Kaliszan,Cybulski,Strzalkowska,Chilmonczyk
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p. 3671 - 3676
(2007/10/03)
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- Crystal structures of 1,2,5-trimethoxy-3-(1-propenyl)benzene and 1,3,5-trimethoxy-2-(1-propenyl)benzene
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The crystal structures of 1,2,5-trimethoxy-3-(1-propenyl)benzene (D) and 1,3,5-trimethoxy-2-(1-propenyl)benzene (F) have been determined by X-ray diffraction methods. The compounds crystallize in the monoclinic system, space group P21/c for (D)
- Wolska,Poplawski,Lozowicka
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p. 2331 - 2341
(2007/10/03)
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