Synthesis and molecular structure of bis(benzo)aza-14-crown-4 ethers with 7-azabicyclo[3.3.1]nonane and homologous fragments

Левов, А. Н.; Komarov, Arseniy I.; Солдатенков, А. Т.; Avramenko, G. V.; Soldatova, S. A.; Khrustalev, Victor N.

doi:10.1134/s1070428008110183

Cited by 17 publications

(16 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For related compounds, see: Levov et al (2006Levov et al ( , 2008; Anh et al (2008); Hieu et al (2011); Khieu et al (2011). Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

et al. 2012

View full text Add to dashboard Cite

The title compound, C39H37NO8, is a product of the Michael addition of the cyclic secondary amine subunit of aza-14-crown-4 ether to dimethyl acetylenedicarboxylate. The piperidinone ring exhibits a distorted chair conformation and the dimethyl acetylenedicarboxylate fragment has a cis configuration with a dihedral angle of 56.61 (5)° between the two carboxylate groups. The crystal packing is stabilized by the weak C—H⋯O hydrogen bonds.

show abstract

“…For related compounds, see: Levov et al (2006Levov et al ( , 2008; Anh et al (2008); Hieu et al (2011); Khieu et al (2011). Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

et al. 2012

View full text Add to dashboard Cite

show abstract

“…For general background to the design, synthesis and applications of macrocyclic ligands for coordination and supramolecular chemistry, see: Hiraoka (1978); Pedersen (1988); Gokel & Murillo (1996); Bradshaw & Izatt (1997). For related compounds, see: Levov et al (2006Levov et al ( , 2008; Komarova et al (2008); Anh et al (2008Anh et al ( , 2012a; Hieu et al (2011); Khieu et al (2011); Sokol et al (2011).…”

Section: Related Literaturementioning

confidence: 99%

“…Design, synthesis and applications of macrocyclic ligands for coordination and supramolecular chemistry draw very great attention of investigators during the last several decades (Hiraoka, 1978;Pedersen, 1988;Gokel & Murillo, 1996;Bradshaw & Izatt, 1997). Recently we have developed the effective methods of synthesis of azacrown ethers containing piperidine (Levov et al, 2006(Levov et al, , 2008Anh et al, 2008Anh et al, , 2012aAnh et al, , 2012b, perhydropyrimidine (Hieu et al, 2011), perhydrotriazine (Khieu et al, 2011) and bispidine (Komarova et al, 2008;Sokol et al, 2011) subunits.…”

Section: S1 Commentmentioning

confidence: 99%

24-Acetyl-8,11,14-trioxa-24,27-diazapentacyclo[19.5.1.1^22,26.0^2,7.0^15,20]octacosa-2,4,6,15(20),16,18-hexaen-28-one

Anh¹,

Hieu²,

Солдатенков³

et al. 2012

Acta Cryst E

View full text Add to dashboard Cite

The title compound, C25H28N2O5, is a product of the Petrenko–Kritchenko condensation of N-acetylpiperidone with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate. The molecule comprises a fused pentacyclic system containing an aza-14-crown-3-ether macrocycle, two piperidone and two benzene rings. The aza-14-crown-3-ether ring adopts a bowl conformation. The dihedral angle between the benzene rings fused to the aza-14-crown-4-ether unit is 70.18 (4)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The conformation of the central piperidone ring is determined by two intramolecular N—H⋯O hydrogen bonds. In the crystal, molecules are linked by weak C—H⋯O interactions into chains along [010].

show abstract

“…Design, synthesis and applications of macrocyclic ligands for coordination and supramolecular chemistry draw very great attention of investigators during the last forty years (Hiraoka, 1978;Pedersen, 1988;Gokel & Murillo, 1996;Bradshaw & Izatt, 1997). Recently we have developed the effective methods of synthesis of azacrown ethers containing piperidine (Levov et al, 2006(Levov et al, , 2008Anh et al, 2008Anh et al, , 2012, perhydropyrimidine (Hieu et al, 2011) and perhydrotriazine subunits (Khieu et al, 2011).…”

Section: S1 Commentmentioning

confidence: 99%

Dimethyl 2-[22,24-dimethyl-23-oxo-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

Anh¹,

Hieu²,

Солдатенков³

et al. 2012

Acta Cryst E

View full text Add to dashboard Cite

The title compound, C29H33NO8, is a product of the Michael addition of the cyclic secondary amine subunit of the aza-14-crown-4 ether to dimethyl acetylenedicarboxylate. The piperidinone ring exhibits a distorted chair conformation, and the dimethyl ethylenedicarboxylate fragment has a cis configuration with a dihedral angle of 78.96 (5)° between the two carboxylate groups. The crystal packing is stabilized by weak C—H⋯O hydrogen bonds.

show abstract

Synthesis and molecular structure of bis(benzo)aza-14-crown-4 ethers with 7-azabicyclo[3.3.1]nonane and homologous fragments

Cited by 17 publications

References 1 publication

Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

24-Acetyl-8,11,14-trioxa-24,27-diazapentacyclo[19.5.1.1^22,26.0^2,7.0^15,20]octacosa-2,4,6,15(20),16,18-hexaen-28-one

Dimethyl 2-[22,24-dimethyl-23-oxo-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

Contact Info

Product

Resources

About

Synthesis and molecular structure of bis(benzo)aza-14-crown-4 ethers with 7-azabicyclo[3.3.1]nonane and homologous fragments

Cited by 17 publications

References 1 publication

Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.02,7.015,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.02,7.015,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

24-Acetyl-8,11,14-trioxa-24,27-diazapentacyclo[19.5.1.122,26.02,7.015,20]octacosa-2,4,6,15(20),16,18-hexaen-28-one

Dimethyl 2-[22,24-dimethyl-23-oxo-8,11,14-trioxa-25-azatetracyclo[19.3.1.02,7.015,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

Contact Info

Product

Resources

About

Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

24-Acetyl-8,11,14-trioxa-24,27-diazapentacyclo[19.5.1.1^22,26.0^2,7.0^15,20]octacosa-2,4,6,15(20),16,18-hexaen-28-one

Dimethyl 2-[22,24-dimethyl-23-oxo-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate