Corrigendum to “The structure of McN-5652” [Bioorg. Med. Chem. 9 (2001) 2105]

Schulze, Oliver; Schmidt, Ulrich; Voß, Jürgen; Nebeling, B.; Adiwidjaja, Ḡunadi; Scharwächter, Klaus

doi:10.1016/s0968-0896(02)00112-8

Cited by 4 publications

(2 citation statements)

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“…mp 44 °C. 1 H NMR (DMSO- d 6 , 360 MHz): 7.83−7.81 (m, 2H), 7.45−7.43 (m, 3H), 3.94 (t, J = 7.3 Hz, 2H), 2.91 (t, J = 8.2, 2H), 1.98−1.89 (m, 2H); MS (pos. APCI): m / z 146.2.…”

Section: Methodsmentioning

confidence: 99%

Palladium(0)-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids with Cyclic Thioamides. Selective Carbon−Carbon Bond Formation for the Functionalization of Heterocycles^†

2007

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The palladium-catalyzed cross-coupling of cyclic thioamides with arylboronic acids in the presence of stoichiometric amounts of a copper(I) cofactor is described. The desulfitative carbon-carbon cross-coupling protocol is performed under neutral conditions and can be applied to a range of heterocyclic structures with embedded thioamide fragments. Successful carbon-carbon cross-coupling is independent of the ring size, aromaticity/nonaromaticity, the presence of additional heteroatoms, or other functional groups in the starting thioamide structure. Employing controlled microwave irradiation at 100 degrees C, most cross-couplings can be completed within 2 h and proceed in high yields. An advantage of using thioamides as starting materials is the fact that the system can be tuned to an alternative carbon-sulfur cross-coupling pathway by changing to stoichiometric copper(II) under oxidative conditions. Both types of thioamide cross-couplings are orthogonal to the traditional base-catalyzed Suzuki-Miyaura cross-coupling of aryl halides with boronic acids.

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“…mp 44 °C. 1 H NMR (DMSO- d 6 , 360 MHz): 7.83−7.81 (m, 2H), 7.45−7.43 (m, 3H), 3.94 (t, J = 7.3 Hz, 2H), 2.91 (t, J = 8.2, 2H), 1.98−1.89 (m, 2H); MS (pos. APCI): m / z 146.2.…”

Section: Methodsmentioning

confidence: 99%

Palladium(0)-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids with Cyclic Thioamides. Selective Carbon−Carbon Bond Formation for the Functionalization of Heterocycles^†

2007

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“…The reaction mixture was left for 18 h at room temperature. The crystalline solid that separated was filtered off and recrystallised from ethanol to give 8.96 g ( 75 C,56.28;H,6.41;N,9.38. Found: C,56.43;H,6.61;N,9.47 %.…”

Section: -C a R B A M O Y L M E T H Y L -6 7 -D I M E T H O X Y -1 -M E T H Y L -3 4dihydroisoquinolinium Chloride (1b)mentioning

confidence: 99%

Synthesis of trans-3-carbamoyl-2-(3-pyridyl)-1,2,5,6-tetrahydro-3H-pyrrolo[2,1-a]isoquinolinium chloride by condensation of 2-carbamoyl-methyl-1-methyl-3,4-dihydroisoquinolinium chloride with nicotinaldehyde

Kleizienė

Degutytė

Berg

et al. 2004

Journal of Chemical Research

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Theoretical Studies on the Adsorption of 5‐Aminotetrazole on Single‐walled Carbon Nanotubes

Chermahini

Kermannezhad

Rezaei

2016

J Chinese Chemical Soc

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In the present study, the adsorption of different isomers of 5‐aminotetrazole as an important precursor of high energetic materials on single walled carbon nanotubes (SWCNTs) with different sizes including (5,5), (6,6) and (7,7) chiralities using density functional theory calculations is investigated. Different adsorption modes including edge, parallel and perpendicular to carbon nanotubes have been investigated. It was found that three different isomers of 5‐aminotetrazole named 1H, 2H and imino forms physically adsorbed on sidewall and end of nanotubes. The adsorption energies for the parallel and perpendicular modes found in the range of −8.25 to −13.16 and −3.74 to −9.42 kcal/mol, respectively. In addition, for the edge mode the adsorption energies are found in the range of −13.01 to −24.5 kcal/mol. On the other hands, from the HOMO/LUMO gap changes, it can be concluded that the SWCNT with (5,5) chirality might sensitively detect the different isomers of 5‐aminotetrazole molecule in comparison with other carbon nanotubes. The global reactivity descriptors, before and after functionalization of 5‐AT tautomers onto the SWCNTs are compared and the results analyzed. Based on calculated results, the SWCNTs are expected to be a potential adsorbent as well as sensors for the adsorption of 5‐AT in environmental and military systems.

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Corrigendum to “The structure of McN-5652” [Bioorg. Med. Chem. 9 (2001) 2105]

Cited by 4 publications

References 0 publications

Palladium(0)-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids with Cyclic Thioamides. Selective Carbon−Carbon Bond Formation for the Functionalization of Heterocycles^†

Palladium(0)-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids with Cyclic Thioamides. Selective Carbon−Carbon Bond Formation for the Functionalization of Heterocycles^†

Synthesis of trans-3-carbamoyl-2-(3-pyridyl)-1,2,5,6-tetrahydro-3H-pyrrolo[2,1-a]isoquinolinium chloride by condensation of 2-carbamoyl-methyl-1-methyl-3,4-dihydroisoquinolinium chloride with nicotinaldehyde

Theoretical Studies on the Adsorption of 5‐Aminotetrazole on Single‐walled Carbon Nanotubes

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Corrigendum to “The structure of McN-5652” [Bioorg. Med. Chem. 9 (2001) 2105]

Cited by 4 publications

References 0 publications

Palladium(0)-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids with Cyclic Thioamides. Selective Carbon−Carbon Bond Formation for the Functionalization of Heterocycles†

Palladium(0)-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids with Cyclic Thioamides. Selective Carbon−Carbon Bond Formation for the Functionalization of Heterocycles†

Synthesis of trans-3-carbamoyl-2-(3-pyridyl)-1,2,5,6-tetrahydro-3H-pyrrolo[2,1-a]isoquinolinium chloride by condensation of 2-carbamoyl-methyl-1-methyl-3,4-dihydroisoquinolinium chloride with nicotinaldehyde

Theoretical Studies on the Adsorption of 5‐Aminotetrazole on Single‐walled Carbon Nanotubes

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Palladium(0)-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids with Cyclic Thioamides. Selective Carbon−Carbon Bond Formation for the Functionalization of Heterocycles^†

Palladium(0)-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids with Cyclic Thioamides. Selective Carbon−Carbon Bond Formation for the Functionalization of Heterocycles^†