1009-70-7Relevant academic research and scientific papers
Regioselective Synthesis of α- And γ-Amino Quinolinyl Phosphonamides Using N-Heterocyclic Phosphines (NHPs)
Shetty, Manasa,Huang, Hai,Kang, Jun Yong
, p. 700 - 703 (2018)
A regioselective phosphonylation of quinolines for the synthesis of α-amino quinolinyl phosphonamides and γ-amino quinolinyl phosphonamides has been developed under mild reaction conditions. An NHP-thiourea enables selective synthesis of α-amino quinolinyl phosphonamides by a Reissert-type reaction, and an NHP-tosylamide affords γ-amino quinolinyl phosphonamides via a 1,4-conjugate addition reaction. The corresponding amino quinolinyl phosphonate adducts were obtained in moderate to excellent yields (up to 99% yield) and regioselectivities (up to 99:1) with good functional group tolerance.
Catalyst-free synthesis of α1-oxindole-α-hydroxyphosphonates: Via phospha-aldol reaction of isatins employing N-heterocyclic phosphine (NHP)-thiourea
Molleti, Nagaraju,Yong Kang, Jun
, p. 8952 - 8956 (2016)
A highly efficient phospha-aldol reaction for the synthesis of α1-oxindole-α-hydroxyphosphonates is developed utilizing N-heterocyclic phosphine (NHP)-thiourea as a phosphonylation reagent under catalyst, additive free conditions. This methodology encompasses a variety of isatin derivatives to provide α1-oxindole- α-hydroxyphosphonates up to 99% yield.
Amine-Catalyzed Phospha-Michael Reaction of α,β-Unsaturated Aldehydes and Ketones with Multifunctional N-Heterocyclic Phosphine-Thioureas as Phosphonylation Reagent
Huang, Hai,Kang, Jun Yong
, p. 4372 - 4375 (2016)
An efficient amine-catalyzed phospha-Michael addition reaction of α,β-unsaturated aldehydes/ketones with N-heterocyclic phosphines for the synthesis of ?-ketodiazaphosphonates has been developed. With freedom from nucleophile additives, this mild process affords a range of structurally diverse ?-ketodiazaphosphonates in moderate to excellent yields. Importantly, various α,β-unsaturated ketones were also tolerated in this process and gave moderate yields.
Synthesis of thiazol, thiazinan, thiadiazin, thiazolidin, triazine, thioxo-pyrimidin and thioxo-imidazolidine by inter-intra molecular cyclization
Zade, Mangesh N.,Katiya, Manish M.,Deotale, Vinod D.,Sontakke, Madhuri M.,Dhonde, Madhukar G.,Berad, Baliram N.
, p. 1493 - 1500 (2019/05/21)
Syntheses of five and six membered heterocyclic derivatives by the reaction of disubstituted thiocarbamides with interintramolecular cyclizations in catalyst free condition have been reported. The simple product isolation without column, good yields under mild condition, and applicable green matrix are the advantages of present protocol.
A Bench-Stable Vilsmeier Reagent for in situ Alcohol Activation: Synthetic Application in the Synthesis of 2-Amino-2-Thiazolines
Corbett, Michael T.,Caille, Seb
, p. 2845 - 2850 (2017/10/06)
A robust, chemoselective direct condensation/cyclization of thioureas and amino alcohols is described. Employing a bench-stable Vilsmeier reagent, methoxymethylene- N, N -dimethyliminium methyl sulfate, the selective in situ activation of alcohols is achieved with high efficiency and broad functional-group tolerance. The reversible interaction of the Vilsmeier reagent with substrate was key to the success of this activation strategy.
A selective and convenient method for the synthesis of 2- phenylaminothiazolines
Bernacki, April L.,Zhu, Lingyang,Hennings, D. David
supporting information; experimental part, p. 5526 - 5529 (2011/02/24)
A series of 2-phenylaminothiazolines have been prepared from the corresponding N-(2-hydroxyethyl)-N'-phenylthioureas under mild reaction conditions using either thio-CDI (1,1'-thiocarbonyldiimidazole) or CDI (1,1'-carbonyldiimidazole) to promote the cycli
Synthesis and biological activity of novel symmetrical bis-2- phenyliminothiazolidine derivatives
Li, Gang-Yue,Qian, Xu-Hong,Yan, Sheng-Gang,Cui, Jing-Nan,Huang, Qing-Chun,Zhang, Rong,Liu, Feng-Yu,Cui, Da-Wei
, p. 2851 - 2861 (2007/10/03)
A series of novel symmetrical bis-2-phenyliminothiazolidine derivatives were designed and synthesized. The structures of all the title compounds were characterized by 1H NMR and, in some cases, by 13C NMR, IR, and high-resolution mas
Synthesis and QSAR studies in 2-(N-aryl-N-aroyl)amino-4,5-dihydrothiazole derivatives as potential antithrombotic agents
Saxena, Anil K.,Pandey, Suresh K.,Seth,Singh,Dikshit,Carpy
, p. 2025 - 2034 (2007/10/03)
A series of 2-(N-aryl-N-aroyl)amino-4,5-dihydrothiazole derivatives have been synthesized via cyclocondensation of N-aryl thioureas with 2-bromoethylamine hydrobromide followed by the reaction of the product thus obtained with aroyl chlorides. Title compounds were evaluated for their antithrombotic activity in vivo in mice where one of these compound 29 provided 65% protection as compared to 77% protection offered by the standard Indomethacin. Quantitative Structure-Activity Relationship (QSAR) studies were performed on these compounds using physicochemical (hydrophobic, electronic, steric) parameter as independent and antithrombic activity as dependent parameter, where antithrombotic activity correlated best (r > 0.8) with electronic parameters (F, σ or μ) having high statistical significance > 99.9% (F2,22 > 15.0; F2,22α:0.001 = 11.0) suggesting that hydrophobic, steric and resonance factors are insignificant in this set of molecules for the activity.
Synthesis and Biological Activity of 2-Aminothiazolines and 2-Mercaptothiazolines as Octopaminergic Agonists
Hirashima, Akinori,Yoshii, Yutuka,Eto, Morifusa
, p. 2537 - 2546 (2007/10/02)
2-Aminothiazoline derivatives were synthesized by both hydrochloric acid-catalyzed cyclization of thiourea and cyclization of β-aminoalkyl hydrogen sulfate with isothiocyanate in the presence of sodium hydroxide.Substituted 2-mercaptothiazoline derivatives were prepared by alkylation or acylation of the sodium salt of 2-mercaptothiazoline, which was obtained from β-aminoalkyl hydrogen sulfate with carbon disulfide. 2-(4-Chloro-o-toluidino)-2-thiazoline (III-16) was 33percent as effective as octopamine at 100 μM in stimulating adenylate cyclase of Periplaneta americana ventral-nerve-cord homogenates.Its activity was nonadditive to the activity of octopamine.Stimulation of nerve-cord adenylate cyclase activity by III-16 was inhibited by several antagonists, including mianserin, cyproheptadine, chlorpromazine and gramine.The rank-order ability of these antagonists to block the activation by III-16 was identical to the rank-order ability of the same antagonists to block enzyme activation of octopamine.The β-adrenergic antagonist propanolol was less potent.These data suggest that III-16 is a potent and selctive agonist of octopamine-activated adenylate cyclase.Aminothiazolines which activated adenylate cyclase by 10-87percent relative to octopamine also had acaricidal activity at 300 ppm, indicating a correlation between the in vitro octopaminergic-agonist activity and in vivo acaricidal activity of aminothiazolines.
