Five-membered rings. Phospholes

Quin, Louis D.; Quin, G. S.

doi:10.1016/b978-008043952-5/50010-3

Cited by 21 publications

(19 citation statements)

References 143 publications

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“…Organic molecules containing heterocyclic fragments constitute one of the most important research areas in modern organic, bioorganic and medicinal chemistry [ 1 – 3 ]. The importance of such molecules is reflected in their innumerable applications, at both laboratory and industrial scale.…”

Section: Introductionmentioning

confidence: 99%

Heteroatom and solvent effects on molecular properties of formaldehyde and thioformaldehyde symmetrically disubstituted with heterocyclic groups C4H3Y (where Y = O–Po)

Matczak

Domagała

2017

J Mol Model

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In this work several molecular properties of symmetrically disubstituted formaldehyde and thioformaldehyde have been studied using a quantum chemistry approach based on density functional theory. Five-membered heteroaromatic rings containing a single group 16 heteroatom were taken into account as the substituents (i.e., furan-2-yl, thiophen-2-yl, selenophen-2-yl, tellurophen-2-yl, and the experimentally as yet unknown polonophen-2-yl). For the resulting ten formaldehyde and thioformaldehyde derivatives, the geometry, energetics, frontier molecular orbitals, dipole moment and polarizability of their molecules were examined in order to establish the effect of ring heteroatom on these properties. Furthermore, these properties were also determined for the molecules in three solvents of low polarity (benzene, chloroform, and dichloromethane) in order to expand our study to include solvent effects. The dipole moment and polarizability of the investigated molecules show regular variations when the ring heteroatom descends through group 16 and the solvent polarity grows. The heteroatom and/or solvent effects on the part of the studied properties are, however, more complex. An attempt is made to rationalize the observed variations in the molecular properties. The conformational behavior of the investigated molecules was also explored and the conformationally weighted values of dipole moment and polarizability are presented. Graphical abstractSome molecular properties of symmetrically disubstituted formaldehyde and thioformaldehyde Electronic supplementary materialThe online version of this article (doi:10.1007/s00894-017-3435-4) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Heteroatom and solvent effects on molecular properties of formaldehyde and thioformaldehyde symmetrically disubstituted with heterocyclic groups C4H3Y (where Y = O–Po)

Matczak

Domagała

2017

J Mol Model

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“…The almost planar 2H-1,2-azaphosphole ring of complex 11 (mean deviation of 0.02 Å ) showed no unusual atom dis-tances when compared to complex 14 (Figure 2), [15] the only known structure of a P-Cp*-substituted phosphole [27,28] or heterophosphole. [29] As a common structural motif in diester-substituted 2H-1,2-azaphosphole rings [25] the ester group at C16 almost shows an in-plane orientation, whereas the ester group at C-17 is oriented out-of-plane.…”

Section: Discussion Of Selected Structural Datamentioning

confidence: 99%

A New Concept for the Efficient Synthesis of Chiral Phosphorus−Nitrogen−Carbon Cage Compounds

et al. 2003

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A new concept for the efficient synthesis of a chiral phosphorus-nitrogen-carbon cage-compound is reported, which is comprised of a high-yield three-step procedure starting from a P-Cp*-substituted 2H-azaphosphirene complex. Thermolysis of a solution of the latter complex in the presence of Ph 3 PNCN and DMAD afforded the P-Cp*-substituted 2H-1,2-azaphosphole complex 11 in a clean reaction; a further reaction at 75°C with DMAD produced complex 12 via an intermolecular Diels−Alder reaction of the Cp* group. A sub-

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“…N-Heterocycles are structures found in natural and synthetic organic compounds relevant in many chemical and biological aspects. 1 Among them, the imidazo [1,2-a]pyridines are one of the most studied class of heterocycles, due to their therapeutic use as antiviral, 2 antituberculotic, 3 antibacterial, 4 antipsychotic 5 and antitumor agents. 6,7 In this way, the imidazo [1,2-a]pyridine scaffold is present in several established leading drugs, such as Alpidem, Necopidem, Olprinone, Saripidem, Zolimidine and Zolpidem.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound-assisted synthesis of imidazo[1,2-a]pyridines and sequential one-pot preparation of 3-selanyl-imidazo[1,2-a]pyridine derivatives

Vieira¹,

Padilha²,

Nascimento³

et al. 2019

Arkivoc

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A simple and rapid method to synthesize imidazo[1,2-a]pyridines starting from 2-aminopyridine and 2bromoacetophenone derivatives under ultrasonic irradiation was developed. This protocol tolerates a wide range of 2-bromoacetophenone derivatives to produce a variety of imidazo[1,2-a]pyridines in good to excellent yields. Additionally, the one-pot preparation of 3-(organylselanyl)imidazo[1,2-a]pyridines via a sequential method is presented. In this case, different diorganyl diselenides were used as starting material s to afford the corresponding coupling products in excellent yields and short reaction times under sonication. The reactions were conducted in PEG-400, a cheap and nontoxic solvent, compatible with the ultrasound conditions in an environmentally benign process.

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Five-membered rings. Phospholes

Cited by 21 publications

References 143 publications

Heteroatom and solvent effects on molecular properties of formaldehyde and thioformaldehyde symmetrically disubstituted with heterocyclic groups C4H3Y (where Y = O–Po)

Heteroatom and solvent effects on molecular properties of formaldehyde and thioformaldehyde symmetrically disubstituted with heterocyclic groups C4H3Y (where Y = O–Po)

A New Concept for the Efficient Synthesis of Chiral Phosphorus−Nitrogen−Carbon Cage Compounds

Ultrasound-assisted synthesis of imidazo[1,2-a]pyridines and sequential one-pot preparation of 3-selanyl-imidazo[1,2-a]pyridine derivatives

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