FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2334652008> ?p ?o ?g. }

• W2334652008 endingPage "425" @default.
• W2334652008 startingPage "401" @default.
• W2334652008 abstract "This article presents the synthesis of (2R/2S,4R)-2-aryl-thiazolidine-4-carboxylic acids via nucleophilic addition of L-Cysteine on aromatic aldehydes involving a yield and time-effective room temperature reaction in an aqueous DMSO medium in the presence of NaHCO3 as a base. The synthesized diastereomers were spectroscopically characterized and quantified for diastereomeric excess by liquid chromatography-mass spectrometry analysis. The impact of the type and position of substituent in aromatic aldehydes on reaction time, % yield, 1H NMR shift at newly formed chiral center [C(2)-H], and diastereomeric excess (de%) have been investigated. A plausible mechanism for stereoselectivity via an in situ imine intermediate is proposed using real-time IR monitoring of the synthetic reaction based on the significant signals at 1597, 1593 cm−1 for imine (C=N) stretching. The imine mechanism for stereoselectivity was further supported by NMR studies of azomethine 13C NMR signals at 159, 160 δ ppm and by the single crystal structure of hitherto unknown (2S,4R)-3-(tert-butoxycarbonyl)-2-(2-hydroxyphenyl)thiazolidine-4-carboxylic acid (3a) obtained as a major diastereomer in the synthesis of the butyloxy carbonyl (BOC) derivative of (2R/2S,4R)-2-(2-hydroxyphenyl)thiazolidine-4-carboxylic acid. The significant ortho-OH effect of phenolic hydroxyl group leading to strong hydrogen bondings plays a vital role in the formation of 2S,4R BOC derivative stereoselectively. The frontier molecular orbitals, possible electronic excitations, IR band characterizations, and reactivity parameters of newly reported compound (3a) have been predicted using quantum chemical descriptors from density functional theory. The theoretical exploration of experimental spectra using time-dependent DFT indicated a (π–π*) transition between HOMO and LUMO in the ultraviolet region." @default.
• W2334652008 created "2016-06-24" @default.
• W2334652008 creator A5001144690 @default.
• W2334652008 creator A5042554119 @default.
• W2334652008 creator A5049477947 @default.
• W2334652008 creator A5072362474 @default.
• W2334652008 date "2016-03-21" @default.
• W2334652008 modified "2023-10-18" @default.
• W2334652008 title "Crystal structure, computational studies, and stereoselectivity in the synthesis of 2-aryl-thiazolidine-4-carboxylic acids via <i>in situ</i> imine intermediate" @default.
• W2334652008 cites W1692336471 @default.
• W2334652008 cites W1963532073 @default.
• W2334652008 cites W1972421899 @default.
• W2334652008 cites W1974086671 @default.
• W2334652008 cites W1975655843 @default.
• W2334652008 cites W1975987132 @default.
• W2334652008 cites W1983077658 @default.
• W2334652008 cites W1989711033 @default.
• W2334652008 cites W1998397331 @default.
• W2334652008 cites W2008708918 @default.
• W2334652008 cites W2013601329 @default.
• W2334652008 cites W2017574753 @default.
• W2334652008 cites W2025019661 @default.
• W2334652008 cites W2027626333 @default.
• W2334652008 cites W2033745485 @default.
• W2334652008 cites W2038651044 @default.
• W2334652008 cites W2044204984 @default.
• W2334652008 cites W2047341569 @default.
• W2334652008 cites W2051305537 @default.
• W2334652008 cites W2053710944 @default.
• W2334652008 cites W2062395400 @default.
• W2334652008 cites W2062852634 @default.
• W2334652008 cites W2063648512 @default.
• W2334652008 cites W2068300583 @default.
• W2334652008 cites W2078498982 @default.
• W2334652008 cites W2091117881 @default.
• W2334652008 cites W2093360384 @default.
• W2334652008 cites W2094429472 @default.
• W2334652008 cites W2117330287 @default.
• W2334652008 cites W2118774275 @default.
• W2334652008 cites W2160916758 @default.
• W2334652008 cites W2163436041 @default.
• W2334652008 cites W2164144520 @default.
• W2334652008 cites W2316317306 @default.
• W2334652008 cites W2322697410 @default.
• W2334652008 cites W2503005323 @default.
• W2334652008 cites W2952525530 @default.
• W2334652008 cites W2952651485 @default.
• W2334652008 cites W4231649355 @default.
• W2334652008 doi "https://doi.org/10.1080/17415993.2016.1156116" @default.
• W2334652008 hasPublicationYear "2016" @default.
• W2334652008 type Work @default.
• W2334652008 sameAs 2334652008 @default.
• W2334652008 citedByCount "10" @default.
• W2334652008 countsByYear W23346520082018 @default.
• W2334652008 countsByYear W23346520082019 @default.
• W2334652008 countsByYear W23346520082020 @default.
• W2334652008 countsByYear W23346520082022 @default.
• W2334652008 countsByYear W23346520082023 @default.
• W2334652008 crossrefType "journal-article" @default.
• W2334652008 hasAuthorship W2334652008A5001144690 @default.
• W2334652008 hasAuthorship W2334652008A5042554119 @default.
• W2334652008 hasAuthorship W2334652008A5049477947 @default.
• W2334652008 hasAuthorship W2334652008A5072362474 @default.
• W2334652008 hasConcept C138716334 @default.
• W2334652008 hasConcept C142724271 @default.
• W2334652008 hasConcept C161790260 @default.
• W2334652008 hasConcept C178790620 @default.
• W2334652008 hasConcept C181647583 @default.
• W2334652008 hasConcept C185592680 @default.
• W2334652008 hasConcept C204787440 @default.
• W2334652008 hasConcept C2776573223 @default.
• W2334652008 hasConcept C2776590680 @default.
• W2334652008 hasConcept C2776910235 @default.
• W2334652008 hasConcept C2778689049 @default.
• W2334652008 hasConcept C2779074116 @default.
• W2334652008 hasConcept C2779825165 @default.
• W2334652008 hasConcept C2780263894 @default.
• W2334652008 hasConcept C2781076698 @default.
• W2334652008 hasConcept C71240020 @default.
• W2334652008 hasConcept C71924100 @default.
• W2334652008 hasConceptScore W2334652008C138716334 @default.
• W2334652008 hasConceptScore W2334652008C142724271 @default.
• W2334652008 hasConceptScore W2334652008C161790260 @default.
• W2334652008 hasConceptScore W2334652008C178790620 @default.
• W2334652008 hasConceptScore W2334652008C181647583 @default.
• W2334652008 hasConceptScore W2334652008C185592680 @default.
• W2334652008 hasConceptScore W2334652008C204787440 @default.
• W2334652008 hasConceptScore W2334652008C2776573223 @default.
• W2334652008 hasConceptScore W2334652008C2776590680 @default.
• W2334652008 hasConceptScore W2334652008C2776910235 @default.
• W2334652008 hasConceptScore W2334652008C2778689049 @default.
• W2334652008 hasConceptScore W2334652008C2779074116 @default.
• W2334652008 hasConceptScore W2334652008C2779825165 @default.
• W2334652008 hasConceptScore W2334652008C2780263894 @default.
• W2334652008 hasConceptScore W2334652008C2781076698 @default.
• W2334652008 hasConceptScore W2334652008C71240020 @default.
• W2334652008 hasConceptScore W2334652008C71924100 @default.
• W2334652008 hasIssue "4" @default.

• next