Azaphospholes<sup>1,2</sup>: State and Advances

Schmidpeter, Alfred; Bansal, R. K.; Karaghiosoff, Konstantin; Steinmüller, Franz; Spindler, Claudia

doi:10.1080/10426509008038977

Cited by 28 publications

(16 citation statements)

References 5 publications

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“…23 Similarly related compounds can also exhibit 1D (onedimensional) and 2D (two-dimensional) isostructural similarity instead of 3D (three-dimensional) isostructurality. 24,25 N-Aryl benzamidines are an important class of compounds having interesting biological properties, including inhibitor activity towards tyrosine kinases 26 and nitric oxide synthases, 27 and can act as selective D 1 dopamine receptor antagonists. 28 In addition, antimicrobial 29 and antiparasitic [30][31][32] activities have also been reported.…”

Section: Introductionmentioning

confidence: 99%

Occurrence of 3D isostructurality in fluorinated phenyl benzamidines

Dey

Chopra

2017

CrystEngComm

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In the current study, we report the existence of 3D isostructurality behaviour in pairs of isomeric molecules existing as E-Z isomers. The polymorphic forms E1 and E2 of (E)-2-fluoro-N′-(3-phenyl) benzimidamide are individually isostructural with (E)-2-fluoro-N′-phenylbenzimidamide and (E)-2-fluoro-N′-(2fluorophenyl) benzimidamide, respectively. Furthermore, a similar compound, (Z)-3-fluoro-N′-(4fluorophenyl) benzimidamide, is isostructural with (Z)-4-fluoro-N′-(4-fluorophenyl) benzimidamide. The structural feature has been analyzed in terms of the nature and energetics of the equivalent supramolecular building blocks associated with the presence of various intermolecular interactions in the crystal packing. The crystal packing similarities have been investigated quantitatively via XPac analysis and the energy vector model. It is noteworthy to observe the presence of a rarely observed N-H⋯F interaction which plays an important role in the crystal packing of [(Z)-3-fluoro-N′-(4-fluorophenyl) benzimidamide]/[(Z)-4-fluoro-N′-(4-fluorophenyl) benzimidamide]. The NCI isosurface signifies the "attractive" nature of the N-H⋯F and N-H⋯π interactions and the different types of C-H⋯F dimeric motifs. An analysis of the two-dimensional fingerprint plots also provides a quantitative understanding of the occurrence of isostructurality in these compounds.

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Section: Introductionmentioning

confidence: 99%

Occurrence of 3D isostructurality in fluorinated phenyl benzamidines

Dey

Chopra

2017

CrystEngComm

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“…10 Aromatic and hetero-aromatic imines particularly those containing strong electron withdrawing groups in the para position of the phenyl ring can undergo E/Z isomerisation around the CN double bond. 11 Furthermore, several N-arylbenzamidines have interesting biological properties, including inhibitor activity towards tyrosine kinases 12 and nitric oxide synthases, 13 and can act as selective D 1 dopamine receptor antagonists. 14 Antimicrobial 15 and antiparasitic 16 activities have also been reported.…”

Section: Introductionmentioning

confidence: 99%

N–H⋯π induced configurational isomerism and the role of temperature in the Z to E isomerization of 2-fluoro-N′-(3-fluorophenyl)benzimidamide

Dey

Chopra

2015

CrystEngComm

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“…In contrast to the behaviour of indolizine [55], the reaction of 2-phosphaindolizines with bromine is regioselective and only the 1-bromo derivative is formed, though in poor yield. The yield could, however, be improved by carrying out the reaction with bromine in presence of Et 3 N, or by using N-bromosuccinimide [56,57] (Scheme 19).…”

Section: Electrophilic Substitutionmentioning

confidence: 99%

“…The reaction of 3-benzoyl-6-butyl-2-phosphaindolizine (4, R 1 = H, R 2 = COPh, R 3 = Bu) with selenophosphonic acid anhydrides (56, R = Ph, 4-MeOC 6 H 4 , 4-Me 2 NC 6 H 4 ) in the presence of Et 3 N, leads to the formation of triethylammonium selenophosphinates (57). In the absence of Et 3 N, however, selenoanhydride 58 is formed as a mixture of two diastereoisomers along with the zwitterionic seleno- …”

Section: Electrophilic Substitutionmentioning

confidence: 99%

Recent Advances in the Chemistry of Anellated Azaphospholes

Bansal¹,

Gupta²,

Kumawat

2007

COC

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Azaphospholes are 6 aromatic heterocycles incorporating at least one 2 , 3 -phosphorus atom and one 3 , 3nitrogen atom. This review covers the synthesis, structural characterization, reactions and theoretical calculations of azaphospholes anellated to a six-or five-membered heterocyclic ring, reported during the last 10-12 years. Three synthetic methods, namely [4+1] cyclocondensation, [3+2] cyclocondensation and 1,5-electrocyclization make a variety of these phosphorus heterocycles available. The aromatic character of these compounds has been confirmed by carrying out density functional theory (DFT) calculations. Mainly 1 H, 13 C and 31 P NMR studies have been employed for the structural characterization. Almost all the functionalities present in the azaphosphole ring have been investigated and electrophilic substitution reactions of the 1-unsubstituted compounds and Diels-Alder reactions as well as 1,2-addition reactions to the >C=P-moiety have been accomplished successfully. The stereo-and regioselectivities observed in the Diels-Alder reactions have been explained on the basis of DFT calculations. Cheletropic cycloadducts formed from [4+1] cycloaddition of o-quinones on the 2 , 3 -P atom have been obtained. A variety of coordination compounds formed bycoordination of the 2 , 3 -P atom have been prepared.

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Azaphospholes^1,2: State and Advances

Cited by 28 publications

References 5 publications

Occurrence of 3D isostructurality in fluorinated phenyl benzamidines

Occurrence of 3D isostructurality in fluorinated phenyl benzamidines

N–H⋯π induced configurational isomerism and the role of temperature in the Z to E isomerization of 2-fluoro-N′-(3-fluorophenyl)benzimidamide

Recent Advances in the Chemistry of Anellated Azaphospholes

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Azaphospholes1,2: State and Advances

Cited by 28 publications

References 5 publications

Occurrence of 3D isostructurality in fluorinated phenyl benzamidines

Occurrence of 3D isostructurality in fluorinated phenyl benzamidines

N–H⋯π induced configurational isomerism and the role of temperature in the Z to E isomerization of 2-fluoro-N′-(3-fluorophenyl)benzimidamide

Recent Advances in the Chemistry of Anellated Azaphospholes

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Azaphospholes^1,2: State and Advances