Isotopically labeled sulfur compounds and synthetic selenium and tellurium analogues to study sulfur metabolism in marine bacteria

• Nelson L. Brock,
• Christian A. Citron,
• Claudia Zell,
• Martine Berger,
• Irene Wagner-Döbler,
• Jörn Petersen,
• Thorsten Brinkhoff,
• Meinhard Simon and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 942–950, doi:10.3762/bjoc.9.108

• order rhizobiales, a close relative of Roseobacter clade bacteria. In addition, the sulfur volatiles bis(methylthio)methane (22), S-methyl propanethioate (23), 4-(methylthio)butan-2-one (24), S-methyl 3-(methylthio)propanethioate (25), and benzothiazole (26) were found in strain-specific patterns

Synthesis of 2,3-dihydronaphtho[2,3-d][1,3]thiazole-4,9-diones and 2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-diones and novel ring contraction and fusion reaction of 3H-spiro[1,3-thiazole-2,1'-cyclohexanes] into 2,3,4,5-tetrahydro-1H-carbazole-6,11-diones

• Lidia S. Konstantinova,
• Kirill A. Lysov,
• Ljudmila I. Souvorova and
• Oleg A. Rakitin

Beilstein J. Org. Chem. 2013, 9, 577–584, doi:10.3762/bjoc.9.62

• , there exists only a single example of the thiazole conversion to thiazole-2-thione, i.e., heating of 3-methyl-2,3-dihydro-1,3-benzothiazole with elemental sulfur at 200 °C for 0.5 h giving 3-methyl-1,3-benzothiazole-2(3H)-thione [17]. We described a similar conversion of the methylene group to

Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides

• Silvia M. Soria-Castro and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2013, 9, 467–475, doi:10.3762/bjoc.9.50

• h at 110 °C, has also been reported [52]. As part of our ongoing study on sulfur chemistry, we are interested in the one-pot synthesis of target heterocycles such as the Beaucage reagent and benzothiazole as well as sulfides by using Cu-catalysis to mediate the C–S bond formation. Herein, we report

• explored the possibility of building a benzothiazole ring by copper-catalyzed reaction of N-(2-iodophenyl)acetamide (13) with 1. Thus, together with benzothiazole 14, the reaction of 13 and 1 in a 1:1.5 ratio, in the presence of CuI/1,10-phenanthroline after 24 h of conventional heating, afforded low

A quantitative approach to nucleophilic organocatalysis

• Herbert Mayr,
• Sami Lakhdar,
• Biplab Maji and
• Armin R. Ofial

Beilstein J. Org. Chem. 2012, 8, 1458–1478, doi:10.3762/bjoc.8.166

• atom in the benzothiazole by a NCH3 group (55b → 55c) shows that imidazole derivatives are approximately four orders of magnitude more reactive than structurally analogous thiazole derivatives, which can, again, be assigned to the different electronegativities of sulfur and nitrogen. Conclusion

Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series

• Cécile Verrier,
• Pierrik Lassalas,
• Laure Théveau,
• Guy Quéguiner,
• François Trécourt,
• Francis Marsais and
• Christophe Hoarau

Beilstein J. Org. Chem. 2011, 7, 1584–1601, doi:10.3762/bjoc.7.187

• -formylthiophene by using Cu(I) cocatalyst and 1,10-phenanthroline in DMA solvent (Scheme 31a) [82]. This year, Oliaf studied more specifically the palladium- and copper-catalyzed oxidative C–H/C–H cross-coupling of various electron-rich 1,3-diazoles and reported notably the direct coupling of benzothiazole with

Development of the titanium–TADDOLate-catalyzed asymmetric fluorination of β-ketoesters

• Lukas Hintermann,
• Mauro Perseghini and
• Antonio Togni

Beilstein J. Org. Chem. 2011, 7, 1421–1435, doi:10.3762/bjoc.7.166

• reagent (3,3-dimethyl-2,3-dihydro-1,2-benzothiazole-1,1-dioxide) [86][87]; p-TsN(F)Me [88]; NFColl = N-fluorocollidinium tetrafluoroborate and NFPy = N-fluoropyridinium tetrafluoroborate [72][89]; F2-bipy = 1,1'-difluoro-bipyridinium bis(tetrafluoroborate) [90]. 1H NMR spectra of a species of the type A

Approaches towards the synthesis of 5-aminopyrazoles

• Ranjana Aggarwal,
• Vinod Kumar,
• Rajiv Kumar and
• Shiv P. Singh

Beilstein J. Org. Chem. 2011, 7, 179–197, doi:10.3762/bjoc.7.25

• intermediacy of the acyclic cyano derivative 127 (Scheme 34) [76]. Hydrazonoyl chlorides 129 on treatment with benzothiazole-2-acetonitrile in ethanolic sodium ethoxide solution at room temperature afforded intermediate hydrazones 130 which on cyclization gave products identified as 3-substituted 5-amino-1

[3.3]Dithia-bridged cyclophanes featuring a thienothiophene ring: synthesis, structures and conformational analysis

• Sabir H. Mashraqui,
• Yogesh Sanghvikar,
• Shailesh Ghadhigaonkar,
• Sukeerthi Kumar,
• Auke Meetsma and
• Elise Trân Huu Dâu

Beilstein J. Org. Chem. 2009, 5, No. 74, doi:10.3762/bjoc.5.74

• conformationally restricted and freely interconverting thia-bridged systems have been identified [7][8][9][10][11][12][13][14][15][16][17]. Cyclophanes incorporating simple heteronuclei such as furan, thiophene, pyridine, pyridazine and benzothiazole are abundantly known [1][2][3]. Despite the known structural

Enantiospecific synthesis of [2.2]paracyclophane- 4-thiol and derivatives

• Gareth J. Rowlands and
• Richard J. Seacome

Beilstein J. Org. Chem. 2009, 5, No. 9, doi:10.3762/bjoc.5.9

• describes a simple route to enantiomerically enriched [2.2]paracyclophane-4-thiol via the stereospecific introduction of a chiral sulfoxide to the [2.2]paracyclophane skeleton. The first synthesis of an enantiomerically enriched planar chiral benzothiazole is also reported. Keywords: heterocycle; [2.2

• demonstrated in the synthesis of the planar chiral benzothiazole (Rp)-10 (Scheme 2). Benzothiazoles are important heterocycles having found use as dyes, pharmaceuticals and ligands in catalysis [42]. Planar chiral heterocycles are still rare but show considerable potential as probes in stereocontrolled

• has the potential to produce a wide-range of thiol derivatives and this has permitted the first synthesis of a planar chiral benzothiazole, [2.2](4,7)benzo[d]thiazoloparacyclophane. The use of these thiols in asymmetric synthesis is currently being investigated and will be reported in due course