Novel boron chelate complexes from the reaction of salicylaldehydes, tertiary amines, and diphenylborinic or phenylboronic acid. Crystal and molecular structures of two new types of chelated organoborate salts

1997 ◽  
Vol 75 (9) ◽  
pp. 1203-1214 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Jörg Metge ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Tertiary Amine ◽  
Phenylboronic Acid ◽  
Reaction System ◽  
Organoboron Compound ◽  
Ammonium Cation ◽  
Acid Anhydride ◽  
Molecular Structures ◽  
One Pot ◽  
Space Group ◽  
Three Component Reaction

The one-pot reaction of equimolar amounts of salicylaldehyde, diphenylborinic acid anhydride, and a tertiary amine in the presence of an alkanol (R′OH) led to the addition of R′OH to the aldehyde group and the formation of an O,O-acetal moiety within the chelate anion with the charge balanced by an ammonium cation arising from the tertiary amine. Exchanging the diphenylborinic acid in the three-component reaction system for phenylboronic acid did not give the analogous adduct or chelate but one additional mole equivalent of phenylboronic acid (anhydride) was incorporated, leading to a polycyclic anion containing pyroboronate and acetal boronate functions with an associated ammonium cation. Crystals of 1-methylpiperidinium 4-ethoxy-2,2-diphenyl-1,3-dioxa-2-borata-1,2,3,4-tetrahydronaphthalenate, 6d, are monoclinic, a = 9.522(1), b = 17.703(1), c = 14.974(1) Å, β = 98.275(10)°, Z = 4, space group P21/n, and those of 1-methylpiperidinium 6,10-epoxy-4-methoxy-6,8-diphenyl-5,7,9-trioxa-8-bora-6-borata-5,6,7,8,9,10-hexahydrobenzocyclooctenate, 10e, are monoclinic, a = 7.968(1), b = 19.3707(4), c = 15.9400(5) Å, β = 100.186(5)°, Z = 4, space group P21/n, The structures were solved by direct methods and refined by full-matrix least-squares procedures to R = 0.050 and 0.033 (Rw = 0.040 and 0.032) for 2815 and 3529 reflections with I ≥ 3σ(F2), respectively. Compounds 6d and 10e are both representative of new classes of organoboron chelates. Keywords: salicylaldehyde semiacetal diphenylboron chelate, salicylaldehyde bisboronate, organoboron compound, crystal structure.

C-(2-Hydroxyaryl)-N-(2-hydroxyphenylmethyl)nitrones as regioselective bidentate ligands in boron chelate formation. Crystal and molecular structures of a diphenylboron complex and its parent ligand

1998 ◽  
Vol 76 (7) ◽  
pp. 1082-1092 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Jörg Metge ◽  
Steven J Rettig ◽  
James Trotter
Keyword(s):  
Direct Methods ◽  
Acid Anhydride ◽  
Molecular Structures ◽  
Bidentate Ligands ◽  
Full Matrix ◽  
Space Group ◽  
Crystal And Molecular Structures ◽  
Chelate Formation ◽  
Boron Chelate ◽  
Parent Ligand

The C-(2-hydroxyaryl)-N-(2-hydroxyphenylmethyl)nitrones 5 are synthesized by the condensation of variously substituted salicylaldehydes with N-(2-hydroxyphenylmethyl)-hydroxylamine. These nitrones react with diphenylborinic acid anhydride to form seven-membered diphenylboron chelates 6. Crystals of C-(4-diethylamino-2-hydroxyphenyl)-N-(2-hydroxyphenylmethyl)nitrone, 5d, are monoclinic, a = 6.911(2), b = 10.663(2), c = 22.951(1) Å, β = 97.33(1)°, Z = 4, space group P21/n, and those of 4-dimethylamino-8-(2-hydroxyphenylmethyl)-6,6-diphenyl-5,7-dioxa-8-azonia-6-borata-6,7-dihydro-5H-benzocycloheptene-ethanol, 6d·EtOH, are monoclinic, a = 9.069(2), b = 29.881(1), c = 11.1883(6) Å, β = 109.426(9)°, Z = 4, space group P21/n. The structures were solved by direct methods and refined by full-matrix least-squares procedures to R = 0.032 and 0.039 (R w = 0.031 and 0.036) for 2510 and 4162 reflections with I > 3σ(I), respectively. Key words : C-(2-hydroxyaryl)-N-(2-hydroxyphenylmethyl)nitrones, organoboron compounds, crystal structures.

One-Pot Synthesis of 1,4-Dihydropyridines via a Phenylboronic Acid Catalyzed Hantzsch Three-Component Reaction

Synlett ◽  
2008 ◽  
Vol 2008 (04) ◽  
pp. 509-512 ◽  
Author(s):  
Abdelmadjid Debache ◽  
Raouf Boulcina ◽  
Ali Belfaitah ◽  
Salah Rhouati ◽  
Bertrand Carboni
Keyword(s):  
Phenylboronic Acid ◽  
One Pot ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
Acid Catalyzed

Structural studies of organoboron compounds. XXI. Crystal and molecular structures of 3-(phenylmethylidene)-4-methyl-1-phenyl-2,6,7-trioxa-3-azonia-1-boratabicyclo-[2.2.2]octane and N-(4-nitrophenylmethylidene)-5-methyl-2-phenyl-1,3-dioxa-2-bora-5-cyclohexaneamine N-oxide

1985 ◽  
Vol 63 (2) ◽  
pp. 509-515 ◽  
Author(s):  
W. Kliegel ◽  
L. Preu ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Least Squares ◽  
Phenylboronic Acid ◽  
Direct Methods ◽  
Molecular Structures ◽  
Structural Studies ◽  
Full Matrix ◽  
Space Group ◽  
Condensation Products ◽  
Crystal And Molecular Structures ◽  
Bicyclic Structure

Crystals of 3-(phenylmethylidene)-4-methyl-1-phenyl-2,6,7-trioxa-3-azonia-1-boratabicyclo[2.2.2]octane are orthorhombic, a = 8.0732(7), b = 11.8499(10), c = 31.679(2) Å, Z = 8, space group Pbca, and those of N-(4-nitrophenylmethylidene)-5-methyl-2-phenyl-1,3-dioxa-2-bora-5-cyclohexaneamine N-oxide are monoclinic, a = 6.1873(6), b = 23.206(2), c = 11.3081(11) Å, β = 92.326(5)°, Z = 4, space group P21/n. Both structures were solved by direct methods and were refined by full-matrix least-squares procedures to final R values of 0.041 and 0.036 for 943 and 1679 reflections with I ≥ 3σ(I), respectively. Both compounds are condensation products of bis(hydroxyalkyl)nitrones and phenylboronic acid. 3-(Phenyl-methylidene)-4-methyl-1-phenyl-2,6,7-trioxa-3-azonia-1-boratabicyclo[2.2.2]octane was found to possess a bicyclic structure resulting from intramolecular O → B coordination (O—B = 1.604(7) Å) and is the first such bicyclic boron compound to be structurally characterized. In N-(4-nitrophenylmethylidene)-5-methyl-2-phenyl-1,3-dioxa-2-bora-5-cyclohexaneamine N-oxide, which has weakened nitrone basicity, the O → B interaction does not occur, resulting in a monocyclic system incorporating a trigonal planar boron atom.

Structural studies of organoboron compounds. XXXIX.1 1,4-Bis(2,2-diethoxyethyl)-6,8-diphenyl-5,7,9-trioxa-4-aza-1-azonia-8- bora-6-boratabicyclo[4.3.0]nonane

1990 ◽  
Vol 68 (10) ◽  
pp. 1791-1796 ◽  
Author(s):  
Henning Amt ◽  
Wolfgang Kliegel ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Crystal Structure ◽  
Least Squares ◽  
Title Compound ◽  
Phenylboronic Acid ◽  
Direct Methods ◽  
Organoboron Compound ◽  
Structural Studies ◽  
Full Matrix ◽  
Space Group ◽  
Bond Lengths

Reaction of N,N′-1,2-ethanediylidenebis(2,2-diethoxyethanamine)- N,N′-dioxide and phenylboronic acid yields the title compound. Crystals of 1,4-bis(2,2-diethoxyethyl)-6,8-diphenyl-5,7,9-trioxa-4-aza-1-azonia-8-bora-6-boratabicyclo[4.3.0]-nonane are triclinic, a = 12.625(2), b = 13.962(2), c = 9.273(1) Å, α = 104.81(1), β = 98.61(1), γ = 106.52(1)°, Z = 2, space group [Formula: see text]. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.058 and Rw = 0.081 for 3677 reflections with I ≥ 3σ(I). The molecule has a bicyclo[4.3.0]nonane structure containing one transannular N—B bond. Important bond lengths are sp3-bomn, N—B = 1.759(3), O—B = 1.435(3) and 1.454(3), C—B = 1.579(4); sp2-boron, O—B = 1.335(3) and 1.404(3), C—B = 1.557(4) Å. The (sp3)B—C(phenyl) bond is the shortest yet reported for this type of compound.Keywords: crystal structure, boron compound, organoboron compound.

Structural studies of organoboron compounds LIX. Reaction of two sterically hindered N,N′-dihydroxyaminals with phenylboronic acid, and the crystal and molecular structures of the resulting 1,3,5-trioxa-6,8-diaza-2,4-diboracyclooctanes and one of the adducts

1993 ◽  
Vol 71 (12) ◽  
pp. 2129-2138 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Gottfried Lubkowitz ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Bond Order ◽  
Phenylboronic Acid ◽  
Direct Methods ◽  
Molecular Structures ◽  
Structural Studies ◽  
Bond Orders ◽  
Space Group ◽  
Crystal And Molecular Structures ◽  
Transannular Interaction ◽  
Sterically Hindered

The syntheses of the sterically hindered N,N′-dihydroxyaminals; N,N′-bis(1-ethoxycarbonyl-1-methylethyl)-N,N′-dihydroxymethanediamine, 1b, and N,N′-bis(1,1-dimethylethyl)-N,N′-dihydroxymethanediamine, 1c, and their reactions with phenylboronic acid to yield the 1,3,5-trioxa-6,8-diaza-2,4-diboracyclooctanes 3 and 4, respectively, are described. Crystals of 1b are tetragonal, a = 18.413(1), c = 9.867(2) Å, Z = 8, space group I41; those of 3 are monoclinic, a = 20.420(4), b = 8.272(4), c = 17.851(5) Å, β = 117.34(1)°, Z = 4, space group C2/c; and those of 4 are monoclinic, a = 9.493(4), b = 16.202(4), c = 14.783(3) Å, β = 101.90(2)°, Z = 4, space group P21/c. The structures were solved by direct methods and were refined by full-matrix least-squares procedures to R = 0.034, 0.039, and 0.040 (Rw = 0.035, 0.034, and 0.036) for 1550, 1438, and 2187 reflections with I ≥ 3σ(F2), respectively. In the solid state, both 3 and 4 exhibit transannular [Formula: see text] interactions. In 3 there are two identical (by symmetry) interactions with [Formula: see text] Å that have estimated bond orders of 0.06, while the single transannular interaction in 4 has N—B = 1.953(3) Å and a bond order of about 0.3. The intermediate-strength transannular interaction in 4 is the first to be reported for this type of molecule.

Structural studies of organoboron compounds LXIII. Reaction of ketoximes with aldehydes and diphenylborinic acid, and the crystal and molecular structures of two different types of boron chelates and one of the precursor aldehyde adducts

1995 ◽  
Vol 73 (6) ◽  
pp. 835-845 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Ulf Riebe ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Chelate Ring ◽  
Direct Methods ◽  
Crystallographic Analysis ◽  
Molecular Structures ◽  
Boron Compounds ◽  
One Pot ◽  
Boron Chelates ◽  
Space Group ◽  
X Ray ◽  
Diphenylboron Chelates

The diphenylboron chelates of ketoxime adducts to formaldehyde and trichloroacetaldehyde (chloral) have been synthesized. The reactions were carried out as three-component one-pot reactions, and also as two-step reactions for the ketoxime chloral adducts, which were isolated and characterized before reaction with oxybis(diphenylborane) to form the diphenylboron chelates. One of the intermediate adducts and two of the diphenylboron chelates have been characterized by X-ray crystallographic analysis. Crystals of O-(2,2,2-trichloro-1-hydroxyethyl)-2-propanonoxime, 8d, are monoclinic, a = 7.010(2), b = 11.832(3), c = 11.684(2) Å, β = 90.48(2)°, Z = 4, space group P21/c; those of 4-isopropylidene-2,2-diphenyl-1,3-dioxa-4-azonia-2-boratacyclopentane, 9a, are orthorhombic, a = 11.098(2), b = 15.364(1), c = 8.715(2) Å, Z = 4, space group P212121; and those of 5-trichloromethyl-2-isopropylidene-3,3-diphenyl-1,4-dioxa-2-azonia-3-boratacyclopentane, 10d, are monoclinic, a = 9.164(2), b = 15.304(3), c = 13.859(2) Å, β = 105.28(1)°, Z = 4, space group P21/n. The structures were solved by direct methods and refined by full-matrix least-squares procedures to R = 0.037, 0.044, and 0.040 (Rw = 0.041, 0.016, and 0.042) for 1082, 1256, and 3062 reflections with I ≥ 3σ(F2), respectively. The X-ray analyses show that the products from the reaction between acetonoxime, oxybis(diphenylborane), and formaldehyde or trichloroacetaldehyde, respectively, possess different boron chelate structures. With formaldehyde a COBON chelate ring is obtained and with trichloroacetaldehyde a BOCON chelate ring is formed. Keywords: boron chelates, boron compounds, organboron compounds, crystal structures.

ChemInform Abstract: One-Pot Synthesis of 1,4-Dihydropyridines via a Phenylboronic Acid Catalyzed Hantzsch Three-Component Reaction.

ChemInform ◽  
2008 ◽  
Vol 39 (27) ◽  
Author(s):  
Abdelmadjid Debache ◽  
Raouf Boulcina ◽  
Ali Belfaitah ◽  
Salah Rhouati ◽  
Bertrand Carboni
Keyword(s):  
Phenylboronic Acid ◽  
One Pot ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
Acid Catalyzed

Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja
Keyword(s):  
Efficient Method ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.

Design, Synthesis, In vitro Cytotoxic Activity Evaluation, and Study of Apoptosis Inducing Effect of New Styrylimidazo[1,2-a]Pyridines as Potent Anti-Breast Cancer Agents

2019 ◽  
Vol 19 (2) ◽  
pp. 265-275 ◽  
Author(s):  
Faeze Khalili ◽  
Sara Akrami ◽  
Malihe Safavi ◽  
Maryam Mohammadi-Khanaposhtani ◽  
Mina Saeedi ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Cytotoxic Activity ◽  
High Yield ◽  
Breast Cancer Cell Lines ◽  
Pyridine Derivatives ◽  
One Pot ◽  
Standard Drug ◽  
Three Component Reaction ◽  
Anti Cancer

Background: This paper reports synthesis, cytotoxic activity, and apoptosis inducing effect of a novel series of styrylimidazo[1,2-a]pyridine derivatives. Objective: In this study, anti-cancer activity of novel styrylimidazo[1,2-a]pyridines was evaluated. Methods: Styrylimidazo[1,2-a]pyridine derivatives 4a-o were synthesized through a one-pot three-component reaction of 2-aminopyridines, cinnamaldehydes, and isocyanides in high yield. All synthesized compounds 4a-o were evaluated against breast cancer cell lines including MDA-MB-231, MCF-7, and T-47D using MTT assay. Apoptosis was evaluated by acridine orange/ethidium bromide staining, cell cycle analysis, and TUNEL assay as the mechanism of cell death. Results: Most of the synthesized compounds exhibited more potent cytotoxicity than standard drug, etoposide. Induction of apoptosis by the most cytotoxic compounds 4f, 4g, 4j, 4n, and 4m was confirmed through mentioned methods. Conclusion: In conclusion, these results confirmed the potency of styrylimidazo[1,2-a]pyridines for further drug discovery developments in the field of anti-cancer agents.

scholarly journals One-Pot Three Component Synthesis of 2-(1H-Benzo[d]thiazole-2-yl)- N-Arylbenzamides in Glycerol Medium

2020 ◽  
Vol 32 (6) ◽  
pp. 1343-1351
Author(s):  
Swathi Thumula ◽  
Venkatesan Srinivasadesikan ◽  
Ravi K. Kottalanka ◽  
S. Rex Jeya Rajkumar ◽  
Balajee Ramchandran
Keyword(s):  
Docking Study ◽  
Molecular Docking Study ◽  
One Pot ◽  
Docking Result ◽  
Three Component Reaction ◽  
Antibacterial Target ◽  
Short Time ◽  
A549 Lung ◽  
Glycerol Medium ◽  
Mcf 7

In this work, a series of 2-(1H-benzo[d]thiazole-2-yl)-N-arylbenzamides is synthesized by using diethyl phthalate, anilines and 2-amino-benzenethiol by one-pot three component synthesis in glycerol medium. Phosphoric acid is used as an effective reagent for this one-pot three component reaction. This reaction got completed in a short time, easy workup and gave an excellent yield in glycerol medium. The N-arylbenzamides was found to have significant cytotoxic potentials against various cancer cells viz., A549 (lung cancer), HeLa (cervical cancer) and MCF-7 (breast cancer) using MTT assay. The molecular docking study is also employed to understand the binding mechanism of N-arylbenzamides against the antibacterial target. The docking result shows the binding energy of compound 4a is -8.6 kcal/mol. The binding affinity is a major concern and it shows that Asn and Thr residues have an interaction with compound 4a.

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