N-Propargylamines: versatile building blocks in the construction of thiazole cores

• S. Arshadi,
• E. Vessally,
• L. Edjlali,
• R. Hosseinzadeh-Khanmiri and
• E. Ghorbani-Kalhor

Beilstein J. Org. Chem. 2017, 13, 625–638, doi:10.3762/bjoc.13.61

• -propargylamines and carbon disulfide The first example of a cyclization of N-propargylamines 1 with carbon disulfide to lead to 5-methylenethiazolidine-2-thiones 2 was reported in 1949 by Batty and Weedon. The reaction took place in refluxing ethanol and generally afforded the corresponding products in good

• yields. It was also observed that products 2 rapidly formed by reaction of 1 with carbon disulfide in the presence of sodium hydroxide as the base in water at 20 °C. Further, the authors showed that treatment of methylene compound 2 with cold concentrated sulfuric acid gave the corresponding isomeric

• high yields through a condensation of commercially available and cheap N-propargylamine, allyl bromide, and carbon disulfide [100]. Conclusion Much work has been carried out during the past decade and has demonstrated that N-propargylamines are one of the most useful and versatile precursors in the

A novel method for heterocyclic amide–thioamide transformations

• Walid Fathalla,
• Ibrahim A. I. Ali and
• Pavel Pazdera

Beilstein J. Org. Chem. 2017, 13, 174–181, doi:10.3762/bjoc.13.20

• efficient method for the transformation of heterocyclic amides to heterocyclic thioamides gained great attention. The reaction of three molar equivalents of cyclohexylamine (1) with one molar equivalent of carbon disulfide in water typically afforded N-cyclohexyl dithiocarbamate cyclohexylammonium salt (2

• cyclohexylamine (60 mmol) and water (50 mL) was added carbon disulfide (21 mmol) dropwise. The reaction mixture was stirred at room temperature for 2 h. The white solid obtained was filtered, washed with water, dried and crystalized from ethanol to provide the pure product. Yield 98% (ethanol 95%) white crystals

[2.2]Paracyclophane derivatives containing tetrathiafulvalene moieties

• Laura G. Sarbu,
• Lucian G. Bahrin,
• Peter G. Jones,
• Lucian M. Birsa and
• Henning Hopf

Beilstein J. Org. Chem. 2015, 11, 1917–1921, doi:10.3762/bjoc.11.207

• dropwise at room temperature to a solution of one equivalent of ketone 1 in dioxane, providing 2-bromo-1-([2.2]paracyclophan-4-yl)ethan-1-one (2) in 81% yield. The reactions of α-bromophenones with salts of dithiocarbamic acid, readily available from the reaction of secondary amines with carbon disulfide

New tris- and pentakis-fused donors containing extended tetrathiafulvalenes: New positive electrode materials for rechargeable batteries

• Shintaro Iwamoto,
• Yuu Inatomi,
• Daisuke Ogi,
• Satoshi Shibayama,
• Yukiko Murakami,
• Minami Kato,
• Kazuyuki Takahashi,
• Kazuyoshi Tanaka,
• Nobuhiko Hojo and
• Yohji Misaki

Beilstein J. Org. Chem. 2015, 11, 1136–1147, doi:10.3762/bjoc.11.128

• . TTP and TTPY are actually less soluble in organic solvents than TTF. In particular, TTPY is barely soluble in common solvents even in carbon disulfide. However, the maximum electrons cannot be utilized for TTP and TTPY batteries because TTP and TTPY dissolve in the electrolyte solutions in their

• cyclic voltammograms of 5d, 7d and 9d measured in a carbon disulfide/benzonitrile (1:1, v/v) solution are shown in Figure 5. As for the tris-fused donors 5d and 7d, four pairs of redox waves were observed. The peak currents of the first and second redox waves were about double those of the others. The

• of 20 and 21. Synthesis of 5–9. Plausible redox processes of 5d and 7d. Plausible redox process of 9d. Orbital energies (eV) of 5a, 6a and 8a. Redox potentials of 5d, 7d, 9d and their related compounds (V vs Fc/Fc+, in benzonitrile/carbon disulfide 1:1, v/v). Charge–discharge parameters for the

Donor–acceptor type co-crystals of arylthio-substituted tetrathiafulvalenes and fullerenes

• Xiaofeng Lu,
• Jibin Sun,
• Shangxi Zhang,
• Longfei Ma,
• Lei Liu,
• Hui Qi,
• Yongliang Shao and
• Xiangfeng Shao

Beilstein J. Org. Chem. 2015, 11, 1043–1051, doi:10.3762/bjoc.11.117

• (12.8 mg, 2 mmol) and C60 (7.2 mg, 1 mmol) were dissolved in carbon disulfide (CS2, 7 mL), and the resulting mixed solution was then placed in the dark hood and left standing without disruption. After 2 weeks, the black block-like single crystalline complex was cropped, and the composition of the

Organocatalyzed enantioselective desymmetrization of aziridines and epoxides

• Ping-An Wang

Beilstein J. Org. Chem. 2013, 9, 1677–1695, doi:10.3762/bjoc.9.192

• generation of carbamodithioic acids from amine and carbon disulfide is also investigated to provide ring-opened products 76 to 80 in high yields and good enantioselectivities (Scheme 11). Chiral 1,2,3-triazolium chlorides Most recently, Ooi [52] and colleagues have described a desymmetrization of meso-N-p

Thermochemistry and photochemistry of spiroketals derived from indan-2-one: Stepwise processes versus coarctate fragmentations

• Götz Bucher,
• Gernot Heitmann and
• Rainer Herges

Beilstein J. Org. Chem. 2013, 9, 1668–1676, doi:10.3762/bjoc.9.191

• fragmentation of 5-ring spiroketal 1 cannot be excluded. It is known that the sulfur analogue 4,7-dihydro-1,3-dithiepine-2-yldidene cleanly fragments into carbon disulfide and butadiene [32]; however, 4,7-dihydro-1,3-dioxepine-2-ylidene does not give carbon dioxide and butadiene [33]. Conclusion In agreement

The rapid generation of isothiocyanates in flow

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 1613–1619, doi:10.3762/bjoc.9.184

• isocyanides [30][31], guanidines [32][33] and thiosemicarbazides [34]. Due to the limited commercial availability of diversely functionalised isothiocyanates chemists normally pursue a de novo synthesis, which most commonly involves the condensation of an amine with thiophosgene or carbon disulfide [35][36

New simple synthesis of ring-fused 4-alkyl-4H-3,1-benzothiazine-2-thiones: Direct formation from carbon disulfide and (E)-3-(2-aminoaryl)acrylates or (E)-3-(2-aminoaryl)acrylonitriles

• Qiuping Ding,
• Yuqing Lin,
• Guangni Ding,
• Fumin Liao,
• Xiaoyan Sang and
• Yi-Yuan Peng

Beilstein J. Org. Chem. 2013, 9, 460–466, doi:10.3762/bjoc.9.49

• and efficient method to construct ring-fused 4-alkyl-4H-3,1-benzothiazine-2-thione derivatives has been developed from carbon disulfide and (E)-3-(2-aminoaryl)acrylates or (E)-3-(2-aminoaryl)acrylonitriles under mild conditions, without the need for a metal catalyst. The newly developed method

• tolerates a wide range of substrates in moderate to excellent yields. Moreover, this method is advantageous over previous ones for the easy synthesis of reactants. Keywords: 4H-3,1-benzothiazine-2-thione; carbon disulfide; (E)-3-(2-aminoaryl)acrylate; (E)-3-(2-aminoaryl)acrylonitrile; Michael addition

• efficient method to construct ring-fused 4-alkyl-4H-3,1-benzothiazine-2-thione derivatives. In the context of this method, carbon disulfide reacted with (E)-3-(2-aminoaryl)acrylates or (E)-3-(2-aminoaryl)acrylonitriles under metal-free conditions at room temperature. The newly developed method tolerates a

Metal–ligand multiple bonds as frustrated Lewis pairs for C–H functionalization

• Matthew T. Whited

Beilstein J. Org. Chem. 2012, 8, 1554–1563, doi:10.3762/bjoc.8.177

• react with simple nucleophiles, a departure from traditional "Fischer-type" carbene reactivity [72]. Second, the iridium center reacts with excess CS2 to reductively couple two carbon disulfide units, generating a metallacyclic IrC2S42– with no new bonds formed to the carbene (Scheme 12) [73

Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity

• Tatyana E. Shubina,
• Matthias Freund,
• Sebastian Schenker,
• Timothy Clark and
• Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2012, 8, 1485–1498, doi:10.3762/bjoc.8.168

• -Methylbenzyl isothiocyanate (2): To a solution of (R)-1-phenylethylamine (3.000 g, 3.151 mL, 24.76 mmol, 1.0 equiv) in anhydrous diethyl ether (20 mL), cooled to 0 °C and under a nitrogen atmosphere, carbon disulfide (12.065 g, 158.46 mmol, 9.6 mL, 6.4 equiv) and N,N′-dicyclohexylcarbodiimide (5.109 g, 24.76

Synthesis, solid-state fluorescence properties, and computational analysis of novel 2-aminobenzo[4,5]thieno[3,2-d]pyrimidine 5,5-dioxides

• Kenichirou Yokota,
• Masayori Hagimori,
• Naoko Mizuyama,
• Yasuhisa Nishimura,
• Hiroshi Fujito,
• Yasuhiro Shigemitsu and
• Yoshinori Tominaga

Beilstein J. Org. Chem. 2012, 8, 266–274, doi:10.3762/bjoc.8.28

• . Results and Discussion Synthesis Heterocyclic ketene dithioacetals (1a–c) were easily prepared by the condensation of the corresponding heterocyclic active methylene compounds with carbon disulfide in sodium hydroxide solution as a base, followed by methylation with dimethyl sulfate [8][9][10]. The

Derivatives of phenyl tribromomethyl sulfone as novel compounds with potential pesticidal activity

• Krzysztof M. Borys,
• Maciej D. Korzyński and
• Zbigniew Ochal

Beilstein J. Org. Chem. 2012, 8, 259–265, doi:10.3762/bjoc.8.27

• with carbon disulfide (Scheme 8) [17]. Moreover, 11h was subjected to the reaction with aromatic isocyanates to give benzimidazolthiocarbamates 11i and 11j. The synthesized compounds were tested for their fungicidal activity. The evaluation was carried out by determining the percentage inhibition of

Advances in synthetic approach to and antifungal activity of triazoles

• Kumari Shalini,
• Nitin Kumar,
• Sushma Drabu and
• Pramod Kumar Sharma

Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79

• , phenoxyacetic acid derivatives and carbon disulfide, respectively. Their antifungal activity was investigated against Aspergillus niger and Fusarium oxysporum. Among the series of synthesized compounds, 7-(3-chlorophenyl)-6,7-dihydro-5H-imidazo[2,1-c][1,2,4]triazole-3-thiol (8, Figure 6) showed the most

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

• Vladimir N. Boiko

Beilstein J. Org. Chem. 2010, 6, 880–921, doi:10.3762/bjoc.6.88

• -nitrochlorobenzene and 2,6-diiodo-4-nitroanisole involve simultaneous reduction and substitution (Scheme 25). Trifluoromethylthiocopper is obtained by reaction of CuBr with AgSCF3 [93][99], the latter is generated from silver fluoride and carbon disulfide [90][100]. To simplify the process, Remy [101][102] suggested

Bis(oxazolines) based on glycopyranosides – steric, configurational and conformational influences on stereoselectivity

• Tobias Minuth and
• Mike M. K. Boysen

Beilstein J. Org. Chem. 2010, 6, No. 23, doi:10.3762/bjoc.6.23

• phthalimido protected precursor 7 (Scheme 3). Introduction of the 3-xanthogenate with carbon disulfide and methyl iodide yielded 17, which was cleanly deoxygenated in high yield by tributyltin hydride under standard conditions [32][33]. From the resulting compound 18, the ligands 3-deoxy glucoBox 21 with

Part 2. Mechanistic aspects of the reduction of S-alkyl- thionocarbonates in the presence of triethylborane and air

• Florent Allais,
• Jean Boivin and
• Van Tai Nguyen

Beilstein J. Org. Chem. 2007, 3, No. 46, doi:10.1186/1860-5397-3-46

• possible source of hydrogen atom. This by-product is produced by reaction of ethyl radical, generated from Et3B, with the xanthate function. Deuterated compounds 3–5 were easily prepared from ethanol, carbon disulfide and ethyl bromide (Figure 2). The results reported in Table 2 clearly show that no

Aroylketene dithioacetal chemistry: facile synthesis of 4-aroyl- 3-methylsulfanyl- 2-tosylpyrroles from aroylketene dithioacetals and TosMIC

• H. Surya Prakash Rao and
• S. Sivakumar

Beilstein J. Org. Chem. 2007, 3, No. 31, doi:10.1186/1860-5397-3-31

• of the cannabinoids. [14] In continuation, and by following the method presently developed, the trisubstituted pyrrole 7 having pyrenoyl substituent was synthesized from AKDTA 6 (Scheme 3). Initially, 1-acetylpyrene 5 was transformed to hitherto unknown pyrene based AKDTA 6 by reaction with carbon

• disulfide and sodium tert-butoxide followed by alkylation with dimethyl sulfate. The reaction of TosMIC 2 with AKDTA 6 provided the trisubstituted pyrrole 7 in excellent yield. As anticipated, the 1H NMR spectrum of pyrenoylpyrrole 7 exhibited a doublet for C2'-H of pyrene unit as a doublet at δ 8.37 ppm