cas 3550-21-8, BENZHYDRYL ISOTHIOCYANATE | Articles data

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Pharmacological characterization of a new series of carbamoylguanidines reveals potent agonism at the H2R and D3R
Even today, the role of the histamine H2 receptor (H2R) in the central nervous system (CNS) is widely unknown. In previous research, many dimeric, high-affinity and subtype-selective carbamoylguanidine-type ligands such as UR-NK22 (5, pKi = 8.07) were reported as H2R agonists. However, their applicability to the study of the H2R in the CNS is compromised by their molecular and pharmacokinetic properties, such as high molecular weight and, consequently, a limited bioavailability. To address the need for more drug-like H2R agonists with high affinity, we synthesized a series of monomeric (thio)carbamoylguanidine-type ligands containing various spacers and side-chain moieties. This structural simplification resulted in potent (partial) agonists (guinea pig right atrium, [35S]GTPγS and β-arrestin2 recruitment assays) with human (h) H2R affinities in the one-digit nanomolar range (pKi (139, UR-KAT523): 8.35; pKi (157, UR-MB-69): 8.69). Most of the compounds presented here exhibited an excellent selectivity profile towards the hH2R, e.g. 157 being at least 3800-fold selective within the histamine receptor family. The structural similarities of our monomeric ligands to pramipexole (6), a dopamine receptor agonist, suggested an investigation of the binding behavior at those receptors. The target compounds were (partial) agonists with moderate affinity at the hD2longR and agonists with high affinity at the hD3R (e.g. pKi (139, UR-KAT523): 7.80; pKi (157, UR-MB-69): 8.06). In summary, we developed a series of novel, more drug-like H2R and D3R agonists for the application in recombinant systems in which either the H2R or the D3R is solely expressed. Furthermore, our ligands are promising lead compounds in the development of selective H2R agonists for future in vivo studies or experiments utilizing primary tissue to unravel the role and function of the H2R in the CNS.
Biselli, Sabrina,Bresinsky, Merlin,Buschauer, Armin,Forster, Lisa,Honisch, Claudia,Pockes, Steffen,Tropmann, Katharina,Bernhardt, Günther
supporting information

(2021/02/12)

Synthesis of thiocarbamoyl fluorides and isothiocyanates using CF3SiMe3 and elemental sulfur or AgSCF3 and KBr with amines
Reactions of thiocarbonyl fluoride derived from cheap, readily available, and widely used CF3SiMe3, elemental sulfur, and KF with secondary amines and primary amines at room temperature in THF provided a wide variety of thiocarbamoyl fluorides and isothiocyanates in moderate to excellent yields, respectively. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF3 reacts with secondary/primary amines under KBr at room temperature, affording quantitative thiocarbamoyl fluorides/isothiocyanates, which feature late-stage application.
Zhen, Long,Fan, Hui,Wang, Xiaoji,Jiang, Liqin
supporting information
p. 2106 - 2110
(2019/03/26)

Synthesis methods for isothiocyanate derivative
The invention discloses synthesis methods for an isothiocyanate derivative. The first synthesis method includes reacting raw materials, including primary amine, trifluoromethyltrimethylsilane, potassium fluoride and sulfur, with an organic solvent at the room temperature to obtain the isothiocyanate derivative. The synthetic isothiocyanate derivative has the advantages of simple operation, safety,high efficiency, non-toxicity, low raw material price, mild condition, high yield, wide application range of substrates, high compatibility of functional groups and the like. The second synthesis method includes reacting raw materials, including the primary amine, silver trifluoromethane and potassium bromide, with the organic solvent at the room temperature to obtain the isothiocyanate derivative. The isothiocyanate derivative has the advantages of simple operation, safety, high efficiency, easy availability of the raw materials, nearly quantitative yield, wide application range of the substrates, applicability to selective post-modification of drugs or complex compounds, and the like.
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Paragraph 0033; 0034; 0035; 0036; 0109; 0110; 0111; 0112

(2019/05/22)

Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water
We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.
Fu, Zhicheng,Yuan, Wenhao,Chen, Ning,Yang, Zhanhui,Xu, Jiaxi
supporting information
p. 4484 - 4491
(2018/10/17)

Systematic structure-activity relationship (SAR) exploration of diarylmethane backbone and discovery of a highly potent novel uric acid transporter 1 (URAT1) inhibitor
In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a-1x and 1ha-1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly potent novel URAT1 inhibitor, 1h, which was 200-and 8-fold more potent than parent lesinurad and benzbromarone, respectively (IC50 = 0.035 μM against human URAT1 for 1h vs. 7.18 μM and 0.28 μM for lesinurad and benzbromarone, respectively). Compound 1h is the most potent URAT1 inhibitor discovered in our laboratories so far and also comparable to the most potent ones currently under development in clinical trials. The present study demonstrates that the diarylmethane backbone represents a very promising molecular scaffold for the design of potent URAT1 inhibitors.
Cai, Wenqing,Wu, Jingwei,Liu, Wei,Xie, Yafei,Liu, Yuqiang,Zhang, Shuo,Xu, Weiren,Tang, Lida,Wang, Jianwu,Zhao, Guilong
(2018/02/07)

Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines
The reaction of thiocarbonyl fluoride, generated from difluorocarbene, with various amines under mild conditions is described. Secondary amines, primary amines, and o-phenylenediamines are converted to thiocarbamoyl fluorides, isothiocyanates, and difluoromethylthiolated heterocycles, respectively. Thiocarbamoyl fluorides were further transformed into trifluoromethylated amines by using a one-pot process. Thiocarbonyl fluoride is generated in situ and is rapidly fully converted in one pot under mild conditions; therefore, no special safety precautions are needed.
Yu, Jiao,Lin, Jin-Hong,Xiao, Ji-Chang
supporting information
p. 16669 - 16673
(2017/12/07)

Multiple binding modes of isothiocyanates that inhibit macrophage migration inhibitory factor
Macrophage migration inhibitory factor (MIF) is a pleiotropic cytokine that has roles in the innate immune response, and also contributes to inflammatory disease. While the biological properties of MIF are closely linked to protein-protein interactions, M
Spencer, Emma S.,Dale, Edward J.,Gommans, Aimée L.,Rutledge, Malcolm T.,Vo, Christine T.,Nakatani, Yoshio,Gamble, Allan B.,Smith, Robin A.J.,Wilbanks, Sigurd M.,Hampton, Mark B.,Tyndall, Joel D.A.
p. 501 - 510
(2015/04/27)

Phosphine-free conversion of alcohols into alkyl thiocyanates using trichloroisocyanuric acid/NH4SCN
A convenient and efficient phosphine-free procedure for the one-pot conversion of primary, secondary and tertiary alcohols into the corresponding alkyl thiocyanates or alkyl isothiocyanates is described using trichloroisocyanuric acid/NH4SCN.
Azadi, Roya,Mokhtari, Babak,Makaremi, Mohamad-Ali
experimental part
p. 77 - 80
(2012/03/26)

Selectfluor F-TEDA-BF4 mediated thiocyanation or isothiocyanation of alcohols by in situ generation of [+SCN] under heterogeneous and neutral conditions
A convenient approach for thiocyanation of alcohols has been developed using ammonium thiocyanate as thiocyanating agent in the presence of a catalytic amount of Selectfluor F-TEDA-BF4 in aqueous acetonitrile. In this method various alcohols generally afforded the corresponding thiocyanates or isothiocyanates directly in good to high yield under heterogeneous and neutral conditions.
Khazaei, Ardeshir,Rahmati, Sadegh,Khalafi-Nezhad, Ali,Saednia, Shahnaz
experimental part
p. 123 - 125
(2012/05/05)

(BIS) UREA AND (BIS) THIOUREA COMPOUNDS AS EPIGENIC MODULATORS OF LYSINE-SPECIFIC DEMETHYLASE 1 AND METHODS OF TREATING DISORDERS
The invention provides for novel (bis)urea and (bis)thiourea compounds which are inhibitors of lysine- specific demethylase 1 (LSD1). Such compounds may be used to treat disorders, including cancer.
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Page/Page column 40

(2011/04/13)

Heterogeneous thiocyanation of benzylic alcohols and silyl and THP ethers, and deprotection of silyl and THP-ethers by [PCl3-n(SiO 2)n] (silphos)
Silicaphosphite (silphos), [PCl3-n(SiO2) n], as a heterogeneous phosphorous compound, catalyzes the thiocyanation of benzylic alcohols and silyl and THP ethers in the presence of I2 and NH4SCN in refluxing CH3CN. The produced silphos oxide byproduct can be easily separated by a simple filtration. Silphos is also used for the efficient and selective deprotection of silyl and THP-ethers to their corresponding alcohols. Copyright
Iranpoor,Firouzabadi,Bahador,Jamalian
experimental part
p. 1972 - 1978
(2010/11/16)

(Bis)urea and (Bis)thiourea inhibitors of lysine-specific demethylase 1 as epigenetic modulators
The recently discovered enzyme lysine-specific demethylase 1 (LSD1) plays an important role in the epigenetic control of gene expression, and aberrant gene silencing secondary to LSD1 overexpression is thought to contribute to the development of cancer. W
Sharma, Shiv K.,Wu, Yu,Steinbergs, Nora,Crowley, Michael L.,Hanson, Allison S.,Casero, Robert A.,Woster, Patrick M.
experimental part
p. 5197 - 5212
(2010/09/09)

In situ-generated N-thiocyanatosuccinimide (NTS) as a highly efficient reagent for the one-pot thiocyanation or isothiocyanation of alcohols
The first application of in situ-generated N-thiocyanatosuccinimide (NTS) for the thiocyanation of alcohols is described. This method can be easily applied for the facile conversion of primary, secondary and tertiary alcohols into the corresponding alkyl thiocyanates or alkyl isothiocyanates in good to excellent yields.
Mokhtari, Babak,Azadi, Roya,Rahmani-Nezhad, Samira
experimental part
p. 6588 - 6589
(2011/02/21)

4-Aminophenyl diphenylphosphinite (APDPP) as a heterogeneous and acid scavenger reagent for thiocyantion or isothiocyanation of alcohols and protected alcohols
4-Aminophenyl diphenylphosphinite (APDPP) as a heterogeneous phosphinite reagent is used for the efficient conversion of alcohols, trimethylsilyl- and tetrahydropyranyl ethers, α-hydroxy phosphonates, and - trimethylsilyloxyphosphonates to their corresponding thiocyanates or isothiocyanates in the presence of Br2 and NH4SCN.
Iranpoor, Nasser,Firouzabadi, Habib,Gholinejad, Mohammad
experimental part
p. 2010 - 2019
(2010/03/24)

Aminoimidazoles as potent and selective human β-secretase (BACE1) inhibitors
The identification of small molecule aminoimidazoles as potent and selective human β-secretase inhibitors is reported. These analogues demonstrate low nannomolar potency for BACE1 in a FRET assay, exhibit comparable activity in a cell-based (ELISA) assay, and show>100x selectivity for the other structurally related aspartyl proteases BACE2, cathepsin D, renin, and pepsin. Our design strategy was supported by molecular modeling studies based on the cocrystal structure of the HTS-hit 3 in the BACE1 active site. These strategies enabled us to integrate pyridine and pyrimidine groups on 3 extending deep into the S3 region of the BACE1 binding pocket and enhancing the ligand's potency. Compound (R)-37 displayed an IC50 value for BACE1 of 20 nM, cellular activity of 90 nM, and > 100-fold selectivity over related aspartyl proteases. Acute oral administration of (R)-37 at 30 mg/kg resulted in a significant 71% reduction of plasma Aβ40 measured at the 6 h time point in a Tg2576 mouse model (p 0.001). 2009 American Chemical Society.
Malamas, Michael S.,Erdei, Jim,Gunawan, Iwan,Barnes, Keith,Johnson, Matthew,Yu, Hui,Turner, Jim,Yun, Hu,Wagner, Erik,Fan, Kristi,Olland, Andrea,Bard, Jonathan,Robichaud, Albert J.
experimental part
p. 6314 - 6323
(2010/03/31)

Synthesis and use of achiral oxazolidine-2-thiones in selective preparation of trans 2,5-disubstituted tetrahydrofurans
The use of achiral N-acetyloxazolidine-2-thiones in the C-glycosylation of lactol acetates has allowed us to prepare with high diastereoselectivity the expected trans 2,5-disubstituted tetrahydrofurans. A study based on the role of the steric hindrance of the N-acetyloxazolidine-2-thiones is reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
Jalce, Gael,Franck, Xavier,Figadere, Bruno
body text
p. 378 - 386
(2009/09/25)

A simple organocatalytic enantioselective synthesis of pregabalin
This paper describes a new procedure for the enantioselective synthesis of the important anticonvulsant drug Pregabalin, which shows biological properties as the (S) enantiomer only. The key step of the synthetic sequence is the Michael addition reaction of Meldrum's acid to a nitroalkene mediated by a quinidine derived thiourea. A variety of novel catalysts bearing different groups at the thiourea moiety were synthesized and tested. The most successful catalyst that incorporates a trityl substituent provided up to 75 % ee of (S)- 4. The conjugate addition reaction was carried out on a multigram scale with low loadings of catalyst (10 mol-%). Moreover, the catalyst can be recycled showing the same capability in chemical yield and asymmetric induction. Then, hydrogenation of nitroalkane 4 followed by decarboxylation of diacid 5 provides Pregabalin hydrochloride in 59% overall yield. Enantioenrichment by crystallization of the free amino acid 1 improves the (S)/(R) enantiomeric ratio to 9:1. ? Wiley-VCII Verlag GmbH & Co. KGaA.
Bassas, Oriol,Huuskonen, Juhani,Rissanen, Kari,Koskinen, Ari M.P.
experimental part
p. 1340 - 1351
(2009/07/26)

Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts
(Chemical Equation Presented) A facile and general protocol for the preparation of isothiocyanates from alkyl and aryl amines is reported. This method relies on a tosyl chloride mediated decomposition of a dithiocarbamate salt that is generated in situ by treatment of an amine with carbon disulfide and triethylamine. Utilizing this protocol, we have prepared 19-alkyl- and arylisothiocyanates in moderate to excellent yield.
Wong, Rince,Dolman, Sarah J.
p. 3969 - 3971
(2008/02/01)

Oxalic acid-catalyzed reaction of alcohols with NaSCN: The effects of additives NaI and i2
Oxalic acid-mediated conversion of alcohols to thiocyante and/or isothiocyanate is described. Aliphatic tertiary alcohols give isothiocyanate by the reaction with NaSCN in the presence of I2, whereas they give thiocyanate without it. Copyright
Miyake, Hideyoshi,Nakao, Yuichi,Sasaki, Mitsuru
p. 1262 - 1263
(2008/02/05)

A new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highly selective bromination, thiocyanation or isothiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers
A new diphenylphosphinite ionic liquid (IL-OPPh2) is introduced. This ionic liquid is used as both a reagent and a solvent to convert alcohols and trimethylsilyl and tetrahydropyranyl (THP) ethers into their corresponding alkyl bromides, thiocyanates or isothiocyanates in the presence of Br2 and SCN- at 80 °C. In this ionic liquid, bromination and thiocyanation of alcohols occurs highly selectively in the presence of trimethylsilyl and THP-ethers and also between different classes of alcohols. The use of this ionic liquid allows easy separation of the desired products from the phosphinate by-product.
Iranpoor, Nasser,Firouzabadi, Habib,Azadi, Roya
p. 5531 - 5534
(2007/10/03)

Preparation of thiocyanates and isothiocyanates from alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers using triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/n-Bu4NSCN system
A combination of triphenylphosphine (PPh3) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) provides a safe and easily available mixed reagent system for the conversion of 1° and 2° alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers to their corresponding thiocyanates and the 3° ones to isothiocyanates in good to high yields.
Iranpoor, Nasser,Firouzabadi, Habib,Nowrouzi, Najmeh
p. 5498 - 5501
(2007/10/03)

Efficient conversion of tetrahydropyranyl (THP) ethers to their corresponding thiocyanates with in-situ-generated Ph3P(SCN) 2
Immediate and efficient one-pot conversion of tetrahydropyranyl (THP) ethers to their corresponding thiocyanates by in-situ-generated Ph 3P(SCN)2 is described. Primary and secondary alkyls and also benzylic THP ethers are converted to their corresponding thiocyanates in excellent yields at room temperature by this method. Copyright Taylor & Francis Inc.
Iranpoor, Nasser,Firouzabadi, Habib,Shaterian, Hamid Reza
p. 2093 - 2096
(2007/10/03)

Nonpeptide bradykinin B2 receptor antagonists: Conversion of rodent-selective bradyzide analogues into potent, orally-active human bradykinin B2 receptor antagonists
The 1-(2-nitrophenyl)thiosemicarbazide (TSC) derivative, (S)-l-[4-(4-benzhydrylthiosemicarbazido)-3-nitrobenzenesulfonyl] pyrrolidine-2-carboxylic acid {2-[(2-dimethylaminoethyl)methylamino]ethyl} amide (bradyzide; (S)-4), was recently disclosed as a novel, potent, orally active nonpeptide bradykinin (BK) B2 receptor antagonist. The compound inhibited the specific binding of [3H]BK to NG108-15 cell membrane preparations (rodent neuroblastoma-glioma) expressing B2 receptors with a Ki of 0.5 ± 0.2 nM. Compound (S)-4 also demonstrated oral efficacy against Freund's complete adjuvant (FCA)-induced mechanical hyperalgesia in rats with an ED50 value of 0.84 μmol/kg. After we optimized the terminal binding determinants projecting from the TSC framework, we found that it was possible to replace the potentially toxicophoric nitro and divalent sulfur moieties with only a 15-fold loss in binding affinity ((S)-14a). However, bradyzide and its congeners were found to have much lower affinities for cloned human B2 receptors, expressed in Cos-7 cells. The hitherto synthesized TSC series was screened against the human B2 receptor, and the dibenzosuberane (DBS) pharmacophore emerged as the key structural requirement for potency. Incorporation of this group resulted in a series of derivatives ((S)-14d,e and 19b-d) with Ki ranges of 10.7-176 nM in NG108-15 cells (expressing the rodent B2 receptor) and 0.79-253 nM in Cos-7 cells (expressing the human B2 receptor). There was no evidence of agonist activity with any of the nonpeptides in any of the cell lines tested. In vivo, oral administration of compound 19c reversed FCA-induced and turpentine-induced mechanical hyperalgesia in rodents with ED50 values of 0.027 and 0.32 μmol/kg, respectively. The selectivity profiles of compounds (S)-14f and (S)-14g were also assessed to determine the conformational and/or steric preferences of the double-ring arrangement. The affinity of (S)-14g for the human B2 receptor suggested that it may be a hydrophobic interaction with the ethane bridge of the DBS moiety that accounts for the increased potency of compounds (S)-14d,e and 19b,c at this receptor, by favoring a binding mode inaccessible to the unsubstituted diphenylmethyl derivative, (S)-4.
Dziadulewicz, Edward K.,Ritchie, Timothy J.,Hallett, Allan,Snell, Christopher R.,Davies, John W.,Wrigglesworth, Roger,Dunstan, Andrew R.,Bloomfield, Graham C.,Drake, Gillian S.,McIntyre, Peter,Brown, Michael C.,Burgess, Gillian M.,Lee, Wai,Davis, Clare,Yaqoob, Mohammed,Phagoo, Steve B.,Phillips, Elsa,Perkins, Martin N.,Campbell, Elizabeth A.,Davis, Andrew J.,Rang, Humphrey P.
p. 2160 - 2172
(2007/10/03)

Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors
The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino-1,3-thiazolyl]-thiophene-2-carboxamidines is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities.
Wilson, Kenneth J.,Illig, Carl R.,Subasinghe, Nalin,Hoffman, James B.,Jonathan Rudolph,Soll, Richard,Molloy, Christopher J.,Bone, Roger,Green, David,Randall, Troy,Zhang, Marie,Lewandowski, Frank A.,Zhou, Zhao,Sharp, Celia,Maguire, Diane,Grasberger, Bruce,DesJarlais, Renee L.,Spurlino, John
p. 915 - 918
(2007/10/03)

Modified guanidines as potential chiral superbases. 2. Preparation of 1,3-unsubstituted and 1-substituted 2-iminoimidazolidine derivatives and a related guanidine by the 2-chloro-1,3-dimethylimidazolinium chloride-induced cyclization of thioureas
Simple preparation methods for modified guanidines were explored for new chiral superbases. Thus, (4S,5S)-4,5-diphenyl- and diastereomeric cyclohexane-fused 2-iminoimidazolidines were prepared from (1S,2S) - 1,2 -diphenylethylenediamine and (1R,2R)- or (1S,2S)-1,2-diaminocyclohexanes through cyclization of protected thiourea intermediates with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a key reaction. In the (4S,5S)-4,5-diphenyl series 1-methyl-2-iminoimidazolidines and 2-diethylaminoimidazoline were also prepared as related guanidines.
Isobe,Fukuda,Tokunaga,Seki,Yamaguchi,Ishikawa
p. 7774 - 7778
(2007/10/03)

Efficient conversion of silyl ethers to thiocyanates with Ph3P(SCN)2
A new and efficient method for the conversion of primary and secondary alkyl, aryl, allyl and benzyl silyl ethers to their corresponding thiocyanates by in-situ generation of Ph3P(SCN)2 is described. The reactions occur immediately at room temperature and provide high to excellent yields of thiocyantes.
Iranpoor,Firouzabadi,Shaterian
p. 65 - 66
(2007/10/03)

Efficient one-pot thiocyanation of primary, secondary and tertiary alcohols by in situ generation of Ph3P(SCN)2. A modified procedure
The preparation of Ph3P(SCN)2 is modified by using a combination of Ph3P, NH4SCN and Br2 at room temperature for the efficient conversion of primary, secondary and tertiary alcohols to their corresponding thiocyanates in excellent yields.
Iranpoor,Firouzabadi,Shaterian
p. 676 - 677
(2007/10/03)

A study on the stability of 5,5-diamino-substituted- 1,4,2- oxathiazoline derivatives
5,5-Diamino-substituted-1,4,2-oxathiazoline derivatives 3 as potential prodrugs, which were easily prepared from hydroximoyl chlorides I and the appropriate thiourea derivatives 2, were decomposed instantaneously into isothiocyanates 4 and the corresponding urea derivatives 5 irrespective of the substituents.
Jung, Keum Shin,Lee, Hong Jung,Song, Hyun Nam,Kim, Jae Nyoung
p. 1879 - 1884
(2007/10/03)

A facile one-pot preparation of isothiocyanates from aldoximes
Isothiocyanates 2a-l were prepared in excellent yields in a one-pot reaction from aldoxime derivatives 1a-l by successive treatment of aldoxime with N-chlorosuccinimide (NCS), thiourea, and triethylamine. The use of HCl/DMF/Oxone system in the reaction instead of NCS was equally effective.
Kim, Jae Nyoung,Jung, Keum Shin,Lee, Hong Jung,Son, Ji Suk
p. 1597 - 1598
(2007/10/03)

The invention of radical reactions. Part XXVI. New thio- and seleno-hydroxamic acids; radical chemistry of their O-acyl derivatives
New thio- and seleno-hydroxamic acids have been synthesized from various 4,4-disubstituted thiazolidine 2,5-dithiones. Their corresponding O-acyl derivatives rearrange photochemically, with visible light, in an identical manner to the acyl derivatives of
Barton,Tachdjian
p. 7091 - 7108
(2007/10/02)