Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems Part IV. 2-Alkyl substituents containing cationic heteroaromatics linked via a C–C bond

Azami, Hidenori; Barrett, David; Sasaki, Hiroshi; Matsuda, Keiji; Sakurai, Minoru; Terasawa, Takeshi; Shirai, Fumiyuki; Chiba, Tsuneo; Matsumoto, Yoshimi; Tawara, Shuichi

doi:10.1016/s0968-0896(00)00314-x

Cited by 19 publications

(11 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For the high coordination numbers, along with special magnetic elements for constructing CPs has attracted a lot of interest [4]. Designing solids with molecules that encode well defined non-covalent interactions has recently become a rapidly growing area of research due to their fascinating molecular and supramolecular structural diversity and potential applications for catalysis [5] and material sciences [6][7][8][9]. Substituted aromatic azo compounds are also important units in the area of nonlinear optics, optical storage media, chemo sensors, photochemical switches and electronic devices.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of bis-(5-bromo-2-methyl-phenyl)-diazene, C14H12Br2N2

Zhang

Feng

et al. 2015

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

C 14 H 12 Br 2 N 2 , monoclinic, P2 1 /c (no. 14), a = 7.07(1) Å, b = 4.079(7) Å, c = 23.86(4) Å, b = 90.13(2)°, V = 687.6 Å 3 , Z = 2, R gt (F) = 0.0346, wR ref (F 2 ) = 0.1166, T = 296 K. Source of materialThe oxidative homo-coupling of anilines to diphenyldiazenes was carried out under air in a 25 ml reaction tube using a Radleys Carousel Reactor™ equipped with a magnetic stirrer. 4-Methoxybenzenamine (15 mg, 4 mmol) was dissolved in 9 ml acetonitrile, CuBr (21 mg, 0.15 mmol) and TEMPO ((2,2,6,6-tetramethylpiperidin-1-yl)oxyl, 23.4 mg, 0.15 mmol) were then added. The reaction mixture was stirred vigorously at 60°C for 18 h. After completion, the reaction mixture was extracted with diethyl ether. Then the organic layer was washed with water and brine. The organic phase was dried with anhydrous magnesium sulfate and filtered through a short silica column. After concentrating the sample under vacuum without further purification, the sample was cooled to room temperature and filtered. The obtained solid was washed by deionized water and dried. Then the yellow block-shaped crystals suitable for X-ray diffraction study were obtained. Experimental detailsAromatic hydrogen atoms were assigned with U iso (H) = 1.2 U eq (C), and included in the final refinement by using geometrical restraints, with d(C-H) = 0.93 Å, the methyl hydrogen atoms were assigned with U iso (H) = 1.5U eq (C), and included in the final refinement by using geometrical restraints, with d(C-H) = 0.96 Å. DiscussionDue to the potentially interesting properties and flexibility in aspects such as composition and topology of coordination polymers (CPs), the crystal engineering of CPs is an exciting area of supramolecular chemistry [1][2][3]. For the high coordination numbers, along with special magnetic elements for constructing CPs has attracted a lot of interest [4]. Designing solids with molecules that encode well defined non-covalent interactions has recently become a rapidly growing area of research due to their fascinating molecular and supramolecular structural diversity and potential applications for catalysis [5] and material sciences [6][7][8][9]. Substituted aromatic azo compounds are also important units in the area of nonlinear optics, optical storage media, chemo sensors, photochemical switches and electronic devices. For these reasons, the efficient synthesis of benzene derivatives continues to attract the interest of synthetic chemists. In this contribution, we report on the interesting new compound. The title structure comprises a 5-bromo-2-methyl-phenylamine in the asymmetric unit. The whole molecule is almost planar with the maximum deviation of 0.0032 Å for N1. In addition, the bond length of N1-C3 is found to be only 1.424(5) Å. The bond C1-Br1 and C4-C7 are single bonds, confirmed by the bond lengths of 1.906(4) Å and 1.517(6) Å, respectively. Further consolidating the stability of the chain structure. Individual chains are entirely cohered together by the weak effect of van der Waals force into a 3D supramolecular network.

show abstract

Section: Discussionmentioning

confidence: 99%

Crystal structure of bis-(5-bromo-2-methyl-phenyl)-diazene, C14H12Br2N2

Zhang

Feng

et al. 2015

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

show abstract

“…The bond angles C13-N4-C17, C11-N2-N3, C11-N2-C13, N3-N2-C13, N4-C13-N2, O1-C8-C9, N1-C8-C9 and C8-N1-C4 are 116. 12 …”

Section: Discussionmentioning

confidence: 99%

Crystal structure of ethyl-5-methyl-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate-(dibenzoylmethane), C17H15N4O

al.²

2012

Zeitschrift für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

“…Recent reviews summarize the current developments. [163][164][165] New carbapenem derivatives have mainly been prepared by the reaction of carbapenem enol phosphate 149 167 with thiols, [168][169][170][171][172][173][174][175] by palladium-catalyzed C-C coupling, 176 or by de novo synthesis of the ring skeleton. 177,178 Scheme 27 Epoxidation of 46, ring-opening, and hydrogenation to allo-threonine precursor 138 153,154…”

Section: B-lactam Antibioticsmentioning

confidence: 99%

α,β-Dehydroamino Acids

Bonauer¹,

Walenzyk²,

König³

2006

Synthesis

View full text Add to dashboard Cite

a,b-Dehydroamino Acids a , b -D e h y d r o a m i n o A c i d sAbstract: Dehydroamino acids are versatile intermediates in organic synthesis and occur as frequent structural motives in natural products and biologically active compounds. This review summarizes recent work (since 1999) on the synthesis, reactions and applications of acyclic and cyclic a,b-dehydroamino acids, a,bdehydroamino esters, and protected a,b-dehydroamino acids. 6Conclusions

show abstract

Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems Part IV. 2-Alkyl substituents containing cationic heteroaromatics linked via a C–C bond

Cited by 19 publications

References 33 publications

Crystal structure of bis-(5-bromo-2-methyl-phenyl)-diazene, C14H12Br2N2

Crystal structure of bis-(5-bromo-2-methyl-phenyl)-diazene, C14H12Br2N2

Crystal structure of ethyl-5-methyl-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate-(dibenzoylmethane), C17H15N4O

α,β-Dehydroamino Acids

Contact Info

Product

Resources

About