- One-pot synthesis of 2-acylbenzothiazoles from 2-aminobenzenethiols and arylacetonitriles via cyclization and sequential oxidation
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An efficient one-pot method to access 2-acylbenzothiazoles via AlCl3-mediated cyclization reaction and I2-promoted sequential oxidation reaction of 2-aminobenzenethiols with arylacetonitriles was developed. This reaction proceeds smoothly with a wide range of arylacetonitriles containing different functional groups to give the corresponding products in moderate to good yields under mild conditions. Moreover, this reaction was conveniently conducted on a gram scale, and the yield is still up to 68%.
- Zhang, Shanshan,Wang, Shiwei,Leng, Yuting,Wu, Yangjie
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supporting information
(2021/08/13)
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- Synthesis of N-Formyl-2-benzoyl Benzothiazolines, 2-Substituted Benzothiazoles, and Symmetrical Disulfides from N-Phenacylbenzothiazolium Bromides
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An unusual aerobic hydrolysis-cascade reaction has been developed with N-phenacylbenzothiazolium bromides by treatment with organic and inorganic base. The corresponding N-formyl-2-benzoyl benzothiazoline and 2-substituted benzothiazole products were obta
- Sahoo, Subas Chandra,Pan, Subhas Chandra
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p. 6208 - 6212
(2019/08/21)
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- A removable functional group strategy for regiodivergent Wittig rearrangement products
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[1,2] and [2,3] Wittig rearrangements are competing reaction pathways, often leading to uncontrollable product distribution. We employ a single removable functional group to fulfill the dual role of attaining a reversible [2,3] and stabilizing radical int
- Alam, Md Nirshad,Lakshmi,Maity, Pradip
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supporting information
p. 8922 - 8926
(2018/12/10)
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- Rhodium Catalyzed Asymmetric Hydrogenation of 2-Pyridine Ketones
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Catalyzed by [Rh(COD)Binapine]BF4, the asymmetric hydrogenation of 2-pyridine ketones has been achieved with excellent enantioselectivities (enantiomeric excesses up to 99%) under mild conditions. This method is suitable for various kinds of 2-pyridine ketones and their derivatives. A number of enantiomerically pure chiral 2-pyridine-aryl/alkyl alcohols were prepared through hydrogenation, which can be used directly in organic synthesis.
- Yang, Hailong,Huo, Ningning,Yang, Ping,Pei, Hao,Lv, Hui,Zhang, Xumu
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p. 4144 - 4147
(2015/09/15)
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- Bu4N+ alkoxide-initiated/autocatalytic addition reactions with organotrimethylsilanes
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The use of Me3SiO-/Bu4N+ as a general activator of organotrimethylsilanes for addition reactions has been established. The broad scope of the method offers trimethylsilanes (including acetate, allyl, propargyl, benzyl, dithiane, heteroaryl, and aryl derivatives) as bench-stable organometallics that can be readily utilized as carbanion equivalents for synthesis. Reactions are achieved at rt without the requirement of specialized precautions that are commonplace for other organometallics.
- Das, Manas,O'Shea, Donal F.
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p. 5595 - 5607
(2014/07/08)
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- Structures and reactivities of O-methylated Breslow intermediates
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As close as you can get: Since Breslow intermediates usually exist in their keto form, their O-protected tautomers may be considered as their closest isolable relatives. A series of these compounds have been synthesized, their structures determined, and the kinetics of their reactions with electrophiles investigated. Copyright
- Maji, Biplab,Mayr, Herbert
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supporting information
p. 10408 - 10412
(2012/11/07)
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- BENZAZOLE DERIVATIVES AS HISTAMINE H4 RECEPTOR LIGANDS
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The present patent application concerns new Iigands of the H4-receptor of formula (I), their process of preparation and their therapeutic use.
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Page/Page column 50
(2012/04/17)
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- Benzazole derivatives as histamine H4 receptor ligands
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The present patent application concerns new ligands of the H4-receptor of formula (I), their process of preparation and their therapeutic use.
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Page/Page column 21
(2012/05/20)
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- PIPERAZINYL DERIVATIVES USEFUL AS MODULATORS OF THE NEUROPEPTIDE Y2 RECEPTOR
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The present invention is directed to piperidinyl and piperazinyl derivatives of formula (II) useful as inhibitors of the NPY Y2 receptor, pharmaceutical compositions comprising said compounds, processes for the preparation of said compounds and the use of said compounds for the treatment and / or prevention of disorders, diseases and conditions mediated by the NPY Y2 receptor.
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Page/Page column 73
(2009/07/18)
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- Stereoselective and competitive [1,2]- and [2,3]-wittig rearrangements of allyl heteroarylalkyl ethers
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Several allyl heteroarylalkyl ethers have been synthesized and then deprotonated with nBuLi in THF at -78°C to give lithium derivatives. The lithium-bearing terminus was either the α- or the α′-carbon atom, depending on the associated proton acidity. In the absence of an external electrophile, a sigmatropic rearrangement occurs, generating a new C-C bond. Heteroarylalkyl homoallylic alcohols and allyl heteroarylalkylic alcohols were obtained as products of stereoselective [2,3]- or [1,2]-Wittig rearrangements, respectively. Homoallylic alcohols were obtained in high yields and with fairly good enantiomeric enrichments when the reactions were carried out in toluene with (-)-sparteine as the external chiral ligand.
- Capriati, Vito,Florio, Saverio,Ingrosso, Giovanni,Granito, Catia,Troisi, Luigino
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p. 478 - 484
(2007/10/03)
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- On the reaction of chloroalkylbenzothiazoles with alkaloides
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2-chloroalkylbenzothiazoles 1a-c react with alkoxides to give substitution and ring-expanded products 3 and 4. The substitution ring-enlargement competition much depends upon the solvent, the substitution reaction being preferred in alcohols and the ring-enlargement in DMF.
- Florio, Saverio,Capriati, Vito,Colli, Gennara
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p. 5839 - 5846
(2007/10/03)
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- On the coupling reaction of 1-benzothiazolyl-2-aza-pentadienyl metals with C-electrophiles
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The coupling reaction of 1-benzothiazolyl-2-aza-pentadienyl metals 3 with carbonyl compounds has been investigated. The reaction of 3 with aldehydes leads to α and/or γ-regioisomeric homoallylic alcohols 8, 9 and 10 depending upon the experimental conditi
- Epifani, Erbana,Florio, Saverio,Perrone, Daniela,Valle, Giovanni
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p. 4465 - 4476
(2007/10/02)
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- REACTION OF BISTRIMETHYLSILYLPEROXIDE WITH 2-BENZOTHIAZOLYLALKYLLITHIUMS: AN UNPRECEDENTED DEMETHYLATION
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Bistrimethylsilylperoxide 1 reacts with 2-benzothiazolylalkyllithiums 3 leading to alkylbenzothiazoles 2, and to benzothiazolylalkyl silyl ethers 4.The reacton of 1 with 3 leading to 2 represents the first example of demethylation of 1.The reaction of 2-benzothiazolyllithium 2g with 1 leads mainly to 2-hydroxybenzothiazole 2h.
- Florio, S.,Troisi, L.
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p. 3721 - 3724
(2007/10/02)
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- General Reactivity of 2-Lithiobenzothiazole to Various Electrophiles and the Use as a Formyl Anion Equivalent in the Synthesis of α-Hydroxy Carbonyl Compounds
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The reaction of 2-lithiobenzothiazole with a variety of electrophiles such as aldehydes, ketones, carboxylic esters, lactones, nitriles, and amides afforded the expected addition and substitution products.Trimethylsilyl chloride readily reacted with the b
- Chikashita, Hidenori,Ishibaba, Megumi,Ori, Keiji,Itoh, Kazuyoshi
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p. 3637 - 3648
(2007/10/02)
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- Herbicidal alpha heterocyclic carbinol carbamates, ureas and N-alpha-substituted acetylcarbamates
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Novel heterocyclic carbinol carbamates, ureas and N-acetyl-carbamates are provided which exhibit primarily preemergence control of broadleaf weeds with good selectivity for corn and certain other crops.
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- Mechanism of Base-Catalyzed Desilylations of Aryl- and Heteroaryltrimethylsilanes
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The influence of different bases on the cleavage of silicium-carbon bonds in aryl- and heteroaryltrimethylsilanes is investigated in the presence of benzaldehyde as electrophilic scavenger for the aryl and heteroaryl anions formed in this process.A reactivity gradation of the various basic catalysts employed is determined from the reactions with 2-(trimethylsilyl)benzothiazole (1).The increase of catalytic activity of the anions parallels that of their ion potential.Attack of the base at the Si atom is postulated as the first step in this reaction sequence, with subsequent dissociation of the pentacoordinated intermediate in the rate-determining step.The carbanion thus liberated rapidly reacts with benzaldehyde.In the differently substituted aryltrimethylsilanes 13, 13', and 13'' the dependency of aryl anion stability in the base-catalyzed carbodesilylation was investigated.The relative rates of reaction correlate with Hammett's ?-constants rather than with the corresponding aryl anion stabilities.
- Effenberger, Franz,Spiegler, Wolfgang
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p. 3872 - 3899
(2007/10/02)
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- REACTION OF 2-LITHIOBENZOTHIAZOLE WITH ELECTROPHILES AND A SYNTHESIS OF α-HYDROXY ALDEHYDES AND KETONES
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The reaction of 2-lithiobenzothiazole with a variety of electrophiles, exept for alkyl halides and styrene oxide, could be effectively accomplished to give the expected products in high yields.The adducts of lithiobenzothiazole to carbonyl compounds could
- Chikashita, Hidenori,Itoh, Kazuyoshi
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p. 295 - 300
(2007/10/02)
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- Alpha-heterocyclic carbinol phosphates
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Novel alpha-heterocyclic carbinol phosphates have been found to exhibit insecticidal and miticidal activity.
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- FLUORIDE ION INDUCED REACTIONS OF OREGANOSILANES WITH SATURATED LACTONES AND αβ-ENONES
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Benzyl-, heteroaryl-, and allylsilanes, under the catalytic action of CsF or silica/TBAF, react in mild conditions with electrophiles such as δ-valero and ε-caprolactone, and with cyclohexen-2-one.
- Ricci, Alfredo,Fiorenza, Mariella,Grifagni, M. Antonietta,Bartolini, Giuseppe,Seconi, Giancarlo
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p. 5079 - 5082
(2007/10/02)
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