- Synthesis and Antioxidant Properties of New Substituted 8-Methyl-6-phenyl-5,6-dihydro-4H-1,3,2-benzodioxaphosphocine-2-oxide Derivatives
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A new route for the synthesis of substituted 8-methyl-6-phenyl-5,6-dihydro-4H-1,3,2-benzodioxaphosphocine-2-oxide derivatives has been developed by using cinnamic acid and p-cresol via condensation, reduction, and followed by phosphorylation steps. The ti
- Siva Prasad,Satheesh Krishna,Santhi Sudha,Sreelakshmi,Nayak,Suresh Reddy
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- Design, Synthesis, and Molecular Modeling of Asymmetric Tolterodine Derivatives as Anticancer Agents
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An efficient and short enantioselective synthesis of (S)- and (R)-tolterodine acid isomers (7a–7i) was performed a 6-methyl-4-phenylchroman-2-one intermediate from inexpensive and commercially available starting materials. A series of tolterodine acid hyb
- Dakarapu, Veera venkatarao,Allaka, Tejeswara Rao,Uppalla, Lav Kumar,Jha, Anjali
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- Palladium Catalyzed Enantioselective Hayashi-Miyaura Reaction for Pharmaceutically Important 4-Aryl-3,4-dihydrocoumarins
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The first palladium-catalyzed asymmetric addition of arylboronic acids to coumarins was successfully established, providing a straightforward asymmetric approach to achieving pharmaceutically important 4-aryl-3,4-dihydrocoumarins. This methodology features easily accessible and bench-stable ligands, a wide substrate scope, mild conditions, and accommodation of electron-withdrawing arylboronic acids.
- Csuk, René,Lai, Jixing,Li, Shengkun,Song, Baoan,Yang, Chen
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supporting information
p. 1329 - 1334
(2022/02/23)
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- Microwave accelerated the solvent-free synthesis of 4-aryl-3,4-dihydrocoumarin via the tandem reaction of cinnamic acids with phenols catalyzed by Amberlyst 15 resin
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Amberlyst 15 resin supported the tandem reaction of cinnamic acids with phenols under solvent-free reaction condition has been introduced to afford 4-aryl-3,4-dihydrocoumarin (neoflavanone) derivatives. The efficiency of solid acidic sulfonic resin (A-15) has been illustrated in two reaction activation methods such as microwave irradiation and conventional heating. The important roles of Amberlyst 15 have been emphasized strongly through the high yields of 4-aryl-3,4-dihydrocoumarin in the shorter time under the assistance of microwave irradiation than of conventional heating, and its high recovery and reusability for six catalyst runs. The original catalyst as well as the recycled catalyst were characterized by XRD and FE-SEM to study the correlation of the surface of reused catalyst and its recyclability.
- Le, Huu-Phuoc,Duong, Cong-Thang,Nguyen, Xuan-Triet,Luu, Thi Xuan Thi
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p. 2187 - 2203
(2021/07/02)
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- Metal-free annulative hydrosulfonation of propiolate esters: synthesis of 4-sulfonates of coumarins and butenolides
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An efficient metal-free and cost-effective method for the synthesis of coumarin and butenolide 4-sulfonates (46 examples) has been developed. The reaction involves addition of sulfonic acids to ethyl propiolates followed by lactonization, resulting in direct formation of coumarin and butenolide 4-sulfonates. This methodology has been elaborated to Sonogashira and Suzuki coupling including the synthesis of rac-tolterodine.
- Fernandes, Rodney A.,Gangani, Ashvin J.,Kunkalkar, Rupesh A.
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p. 3970 - 3984
(2020/03/19)
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- Lewis acid-catalyzed annulative partial dimerization of 3-aryloxyacrylates to 4-arylchroman-2-ones: Synthesis of analogues of tolterodine, RORγ inhibitors and a GPR40 agonist
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A beguiling annulative partial dimerization of 3-aryloxyacrylates to 4-arylchroman-2-ones catalyzed by Lewis acid (BF3·OEt2) has been developed. The reaction involves two molecules of 3-aryloxyacrylate, resulting in the loss of one propiolate molecule to furnish 4-arylchroman-2-one, an important structural motif found in many natural products. This methodology has been elaborated to synthesize analogues of tolterodine, RORγ inhibitors and a GPR40 agonist.
- Kunkalkar, Rupesh A.,Fernandes, Rodney A.
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supporting information
p. 2313 - 2316
(2019/02/27)
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- Hydrolase-mediated resolution of the hemiacetal in 2-chromanols: The impact of remote substitution
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Hydrolase-catalysed dynamic kinetic resolutions of chroman-2-ol and 3-methyl chroman-2-ol can be effected with up to 88% conversion and 92% ee through the use of organic solvents. Extension to the resolution of the tolterodine precursor 1 proved more challenging. The presence of the remote phenyl substituent had a significant impact on the resolution and it was not possible to achieve high enantioselectivity together with efficient conversion from the focussed panel of enzymes screened.
- Gavin, Declan P.,Foley, Aoife,Moody, Thomas S.,Rao Khandavilli,Lawrence, Simon E.,O'Neill, Pat,Maguire, Anita R.
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p. 577 - 585
(2017/05/01)
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- Hydroarylation of cinnamic acid with phenols catalyzed by acidic ionic liquid [H-NMP]HSO4: computational assessment on substituent effect
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Hydroarylation of cinnamic acid with different substituted phenols, in the presence of acidic ionic liquid, N-methyl-2-pyrrolidonum hydrosulfate ([H-NMP]HSO4) gave the corresponding dihydrocoumarins in high yields and excellent selectivity. Amo
- Zadsirjan, Vahideh,Heravi, Majid M.,Tajbakhsh, Mahmoud,Oskooie, Hossein A.,Shiri, Morteza,Hosseinnejad, Tayebeh
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p. 6407 - 6422
(2016/07/06)
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- Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
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4-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H14P5NaW30O110) (PA)
- Escobar, Anglica M.,Ruiz, Diego M.,Autino, Juan C.,Romanelli, Gustavo P.
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p. 10109 - 10123
(2016/01/12)
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- Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling
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Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I2 while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I2. Later reaction occurs via a tandem hydroarylation- esterification process at 120-130°C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2- ones were obtained in 5-85% yields.
- Naik, Mayuri M.,Kamat, Durga P.,Tilve, Santosh G.,Kamat, Vijayendra P.
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p. 5221 - 5233
(2014/07/08)
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- Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling
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Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I2while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I2. Later reaction occurs via a tandem hydroarylation-esterification process at 120-130 °C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2-ones were obtained in 5-85% yields.
- Naik, Mayuri M.,Kamat, Durga P.,Tilve, Santosh G.,Kamat, Vijayendra P.
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p. 5221 - 5233
(2014/12/10)
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- Lewis acid promoted dual bond formation: Facile synthesis of dihydrocoumarins and spiro-tetracyclic dihydrocoumarins
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Lewis acid (FeCl3) mediated dual bond (C-C and C-O) formation for synthesis of 3,4-dihydrocoumarins is presented. This method has successfully delivered a number of dihydrocoumarins containing dense functionalities on the aromatic ring. Significantly, the present method enabled achieving dihydrocoumarins with tertiary as well as quaternary carbon atoms at the benzylic position. Gratifyingly, the novel spiro-tetracyclic lactones have also been dextrously prepared using this process. the Partner Organisations 2014.
- Niharika, Pedireddi,Ramulu, Bokka Venkat,Satyanarayana, Gedu
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p. 4347 - 4360
(2014/06/23)
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- A PROCESS FOR PREPARING FESOTERODINE
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The present invention relates to an improved process for the preparation of Fesoterodine and pharmaceutically acceptable salts thereof. The present invention particularly relates to a process for the preparation of fesoterodine and pharmaceutically acceptable salts thereof which involves use and preparation of R(+) benzyl tolterodine and fumarate salt of R(+)-[4-benzyloxy-3-(3-diisopropylamino-1-phenylpropyl)-phenyl]-methanol.
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Page/Page column 9-10
(2012/10/18)
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- Solvent-free synthesis of 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling of phenols with cinnamic acid catalyzed by molecular iodine
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Molecular iodine was used as a catalyst in the [3+3] cyclocoupling of phenols and cinnamic acids which proceeds via a tandem esterification- hydroarylation process at 120-130 °C under solvent-free conditions. Substituted 4-aryl-3,4-dihydrobenzopyran-2-one
- Kamat, Durga P.,Tilve, Santosh G.,Kamat, Vijayendra P.
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experimental part
p. 4469 - 4472
(2012/09/22)
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- TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes: A novel method for the solid-phase synthesis of dihydrocoumarins and coumarins
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TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno-functionality, followed by traceless cleavage of selenium linker to provide dihydrocoumarins and coumarins in good yields and purities.
- Tang,Li, Wen,Gao, Zhang Yong,Gu, Xi
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experimental part
p. 631 - 634
(2012/07/03)
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- Selective synthesis of 3,4-dihydrocoumarins and chalcones from substituted aryl cinnamic esters
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Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by TiCl4. This method can be used for preparing various coumarin & chalcone compounds.
- Jeon, Jae-Ho,Yang, Deok-Mo,Jun, Jong-Gab
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- A PROCESS FOR THE PREPARATION OF TOLTERODINE TARTRATE
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The present invention relates to provide an improved process for the preparation of tolterodine or salt thereof, comprises a step of reducing 3-(2-methoxy-5-methylphenyl) -3-phenyl propionic acid of formula (III) in the presence of a reducing agent, an acidic reagent and a solvent to obtain 3-(2-methoxy-5-methylphenyl) -3-phenyl propanol of formula (IV).
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Page/Page column 15
(2010/05/13)
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- Rhodium-catalyzed domino conjugate addition-cyclization reactions for the synthesis of a variety of N- and O-heterocycles: Arylboroxines as effective carbon nucleophiles
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Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.
- Park, Ja Ock,Youn, So Won
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supporting information; experimental part
p. 2258 - 2261
(2010/07/17)
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- Co-catalyzed mild and chemoselective reduction of phenyl esters with NaBH4: a practical synthesis of (R)-tolterodine
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CoCl2 catalyzes effectively the chemoselective reduction of phenyl carboxylic esters to the corresponding saturated alcohols in high yields using NaBH4 at ambient conditions. By employing this methodology, the synthesis of (R)-tolterodine, a muscarinic receptor antagonist, has been achieved in high yield and optical purity.
- Jagdale, Arun R.,Sudalai, Arumugam
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p. 3790 - 3793
(2008/09/21)
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- Microwave-assisted one-pot synthesis of dihydrocoumarins from phenols and cinnamoyl chloride
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A facile approach has been developed for the synthesis of dihydrocoumarin derivatives through the reaction of phenols and cinnamoyl chloride in the presence of ecofriendly solid-acid catalyst montmorillonite K-10 via a tandem esterification-Friedel-Crafts
- Zhang, Zhen,Ma, Yuan,Zhao, Yufen
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experimental part
p. 1091 - 1095
(2009/04/04)
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- p-Toluenesulfonic acid mediated hydroarylation of cinnamic acids with anisoles and phenols under metal and solvent-free conditions
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Hydroarylation of cinnamic acids with anisoles and phenols mediated by p-toluenesulfonic acid (p-TSA) under metal and solvent-free conditions gave 3-(4-methoxyphenyl)-3-phenylpropanoic acids and dihydrocoumarins, respectively, in high yields and excellent selectivity.
- Jagdale, Arun R.,Sudalai, Arumugam
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p. 4895 - 4898
(2008/02/08)
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- TOLTERODINE, COMPOSITIONS AND USES THEREOF, AND PREPARATION OF THE SAME
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Racemic tolterodine free base in crystalline form, tolterodine with improved purity, compositions and uses thereof, and processes of preparing the same.
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Page/Page column 11-12
(2008/06/13)
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- An improved, scalable, and impurity-free process for tolterodine tartrate
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Tolterodine tartrate is an anticholinergic muscle relaxant used to treat urinary frequency, urinary urgency, and incontinence in people with unstable bladders. An improved, cost-effective, and impurity-free process for tolterodine tartrate suitable for la
- Srinivas, Keesari,Srinivasan, Neti,Reddy, Kikkuru Srirami,Ramakrishna, Muddasani,Reddy, Chinta Raveendra,Arunagiri, Muthulingam,Kumari, Routhu Lalitha,Venkataraman, Sundaram,Mathad, Vijayavitthal T.
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p. 314 - 318
(2012/12/24)
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- ENANTIOSELECTIVE SYNTHESIS OF ENANTIOMERICALLY ENRICHED COMPOUNDS
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Method of preparing an enantiomerically enriched compound of formula (II) comprising enantioselective hydrogenation of a compound of general formula (I): where W, X and Z have the meanings indicated in the description, to give a compound of general formula (II): where W, Y, T and C* have the meanings indicated in the description, in the presence of a catalyst or its suitable precursor based on Rh, Ru or Ir, having an oxidation state of 0, +1 or +2, and containing at least one enantiomerically enriched chiral ligand.
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Page/Page column 9; 10
(2010/02/10)
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- Novel process and intermediates
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The invention relates to a process for the enantioselective preparation of tolterodine and analogues and salts thereof comprises the steps of: a) enantioselectively reducing the carbonyl function in a compound of formula (II): 1?wherein R1, Rs
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- Synthesis of substituted (±)-3,4-dihydrocoumarins using H-Y zeolite
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Synthesis of substituted (±)-3,4 Dihydrocoumarins were prepared with the reaction between substituted cinnamic acid and phenol catalysed by eco- friendly solid-acid catalyst H-Y zeolite involving esterification followed by ring closure.
- Shukla, Manojkumar R.,Patil, Prashant N.,Wadgaonkar, Prakash P.,Joshi, Prafulla N.,Salunkhe, Manikrao M.
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- Synthesis and structural elucidation of (±)-3,4-dihydrocoumarins by 2D- NOESY spectrum
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(±)-3,4-Dihydrocoumarins have been synthesized in high yield and the structures are confirmed by 2D-NOESY spectrum.
- Shukla,Padiya,Patil,Salunkhe
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p. 372 - 375
(2007/10/03)
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