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Article ; Online: Crystal structure and Hirshfeld surface analysis of ethyl (4R,4aS)-2-methyl-5,8-dioxo-6-phenyl-4a,5,6,7,7a,8-hexahydro-4H-furo[2,3-f]isoindole-4-carboxylate

Vladimir P. Zaytsev / Lala V. Chervyakova / Elena A. Sorokina / Kirill A. Vasilyev / Sevim Türktekin Çelikesir / Mehmet Akkurt / Ajaya Bhattarai

Acta Crystallographica Section E: Crystallographic Communications, Vol 77, Iss 2, Pp 86-

2021 Volume 90

Abstract: In the title compound, C20H19NO5, the central six-membered ring has a slightly distorted half-chair conformation, with puckering parameters of QT = 0.3387 (11) Å, θ = 49.11 (19)° and φ = 167.3 (2)°. The conformation of the fused pyrrolidine ring is that ... ...

Abstract	In the title compound, C20H19NO5, the central six-membered ring has a slightly distorted half-chair conformation, with puckering parameters of QT = 0.3387 (11) Å, θ = 49.11 (19)° and φ = 167.3 (2)°. The conformation of the fused pyrrolidine ring is that of an envelope. Molecules are connected by intermolecular C—H.O hydrogen bonds, C—H.π interactions and π–π stacking interactions [centroid-to-centroid distance = 3.9536 (11) Å, with a slippage of 2.047 Å], forming a three-dimensional network. The most important contributions to the surface contacts are from H.H (46.3%), O.H/H.O (31.5%) and C.H/H.C (17.3%) interactions, as concluded from a Hirshfeld surface analysis.
Keywords	crystal structure ; six-membered ring ; pyrrolidine ring ; furan ring ; hirshfeld analysis ; imdav reaction ; Chemistry ; QD1-999
Language	English
Publishing date	2021-02-01T00:00:00Z
Publisher	International Union of Crystallography
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms

Dmitriy F. Mertsalov / Rosa M. Gomila / Vladimir P. Zaytsev / Mikhail S. Grigoriev / Eugeniya V. Nikitina / Fedor I. Zubkov / Antonio Frontera

Crystals, Vol 11, Iss 1406, p

2021 Volume 1406

Abstract: This manuscript reports the synthesis and X-ray characterization of two octahydro-1H-4,6-epoxycyclopenta[ c ]pyridin-1-one derivatives that contain the four most abundant halogen atoms (Ha) in the structure with the aim of studying the formation of Ha··· ... ...

Abstract	This manuscript reports the synthesis and X-ray characterization of two octahydro-1H-4,6-epoxycyclopenta[ c ]pyridin-1-one derivatives that contain the four most abundant halogen atoms (Ha) in the structure with the aim of studying the formation of Ha···Ha halogen bonding interactions. The anisotropy of electron density at the heavier halogen atoms provokes the formation of multiple Ha···Ha contacts in the solid state. That is, the heavier Ha-atoms exhibit a region of positive electrostatic potential (σ-hole) along the C–Ha bond and a belt of negative electrostatic potential (σ-lumps) around the atoms. The halogen bonding assemblies in both compounds were analyzed using density functional theory (DFT) calculations, molecular electrostatic potential (MEP) surfaces, the quantum theory of “atom-in-molecules” (QTAIM), the noncovalent interaction plot (NCIplot), and the electron localization function (ELF).
Keywords	halogen bonding ; crystal engineering ; supramolecular chemistry ; σ-hole ; Crystallography ; QD901-999
Subject code	540 ; 541
Language	English
Publishing date	2021-11-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
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Article ; Online: Crystal structure of 3-benzyl-2-[(E)-2-(furan-2-yl)ethenyl]-2,3-dihydroquinazolin-4(1H)-one and 3-benzyl-2-[(E)-2-(thiophen-2-yl)ethenyl]-2,3-dihydroquinazolin-4(1H)-one from synchrotron X-ray diffraction

Flavien A. A. Toze / Vladimir P. Zaytsev / Lala V. Chervyakova / Elisaveta A. Kvyatkovskaya / Pavel V. Dorovatovskii / Victor N. Khrustalev

Acta Crystallographica Section E: Crystallographic Communications, Vol 74, Iss 1, Pp 10-

2018 Volume 14

Abstract: The chiral title compounds, C21H18N2O2, (I), and C21H18N2OS, (II) – products of the three-component reaction between benzylamine, isatoic anhydride and furyl- or thienyl-acrolein – are isostructural and form isomorphous racemic crystals. The ... ...

Abstract	The chiral title compounds, C21H18N2O2, (I), and C21H18N2OS, (II) – products of the three-component reaction between benzylamine, isatoic anhydride and furyl- or thienyl-acrolein – are isostructural and form isomorphous racemic crystals. The tetrahydropyrimidine ring in (I) and (II) adopts a sofa conformation. The amino N atom has a trigonal–pyramidal geometry [sum of the bond angles is 347.0° for both (I) and (II)], whereas the amido N atom is flat [sum of the bond angles is 359.3° for both (I) and (II)]. The furyl- and thienylethenyl substituents in (I) and (II) are planar and the conformation about the bridging C=C bond is E. These bulky fragments occupy the axial position at the quaternary C atom of the tetrahydropyrimidine ring, apparently, due to steric reasons. In the crystals, molecules of (I) and (II) form hydrogen-bonded helicoidal chains propagating along [010] by strong intermolecular N—H.O hydrogen bonds.
Keywords	crystal structure ; 2-ethenylquinazolines ; furyl-acrolein ; thienyl-acrolein ; three-component reaction ; synchrotron radiation ; Chemistry ; QD1-999
Subject code	540
Language	English
Publishing date	2018-01-01T00:00:00Z
Publisher	International Union of Crystallography
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Interaction between maleic acid and N-R-furfurylamines

Elisaveta A. Kvyatkovskaya / Vladimir P. Zaytsev / Fedor I. Zubkov / Pavel V. Dorovatovskii / Yan V. Zubavichus / Victor N. Khrustalev

Acta Crystallographica Section E: Crystallographic Communications, Vol 73, Iss 4, Pp 515-

crystal structure of 2-methyl-N-[(5-phenylfuran-2-yl)methyl]propan-2-aminium (2Z)-3-carboxyacrylate and N-[(5-iodofuran-2-yl)methyl]-2-methylpropan-2-aminium (2Z)-3-carboxyprop-2-enoate

2017 Volume 519

Abstract: The title molecular salts, C15H20NO+·C4H3O4−, (I), and C9H15INO+·C4H3O4−, (II), have very similar molecular geometries for both cation and anion. The anions of both (I) and (II) are practically planar (r.m.s. deviations = 0.062 and 0.072 Å, respectively) ...

Abstract	The title molecular salts, C15H20NO+·C4H3O4−, (I), and C9H15INO+·C4H3O4−, (II), have very similar molecular geometries for both cation and anion. The anions of both (I) and (II) are practically planar (r.m.s. deviations = 0.062 and 0.072 Å, respectively) and adopt a rare symmetrical geometry with the hydroxy H atom approximately equidistant from the two O atoms. In their crystals, the cations and anions in both (I) and (II) form tight ionic pairs via strong N—H.O hydrogen bonds, with a roughly perpendicular disposition of the anion to the furan ring of the cation. This ion-pair conformation appears to correlate with the lack of reactivity of these salts in [4 + 2] cycloaddition reactions. In the extended structures of (I) and (II), the ion pairs form hydrogen-bonded chains propagating along [010] and [001], respectively, via N—H.O hydrogen bonds.
Keywords	furans ; Diels–Alder reaction ; maleates ; crystal structure ; synchrotron radiation ; Chemistry ; QD1-999
Subject code	540
Language	English
Publishing date	2017-04-01T00:00:00Z
Publisher	International Union of Crystallography
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Three-component reaction between isatoic anhydride, amine and methyl-substituted furylacrylaldehydes

Vladimir P. Zaytsev / Elena A. Sorokina / Elisaveta A. Kvyatkovskaya / Flavien A. A. Toze / Shashank N. Mhaldar / Pavel V. Dorovatovskii / Victor N. Khrustalev

Acta Crystallographica Section E: Crystallographic Communications, Vol 74, Iss 8, Pp 1101-

crystal structures of 3-benzyl-2-[(E)-2-(5-methylfuran-2-yl)vinyl]-2,3-dihydroquinazolin-4(1H)-one, 3-benzyl-2-[(E)-2-(furan-2-yl)-1-methylvinyl]-2,3-dihydroquinazolin-4(1H)-one and 3-(furan-2-ylmethyl)-2-[(E)-2-(furan-2-yl)-1-methylvinyl]-2,3-dihydroquinazolin-4(1H)-one

2018 Volume 1106

Abstract: Compounds (I), C22H20N2O2, (II), C22H20N2O2 and (III), C20H18N2O3 are the products of three-component reactions between isatoic anhydride, the corresponding amine and 3-(5-methylfuran-2-yl)- or (furan-2-yl)-2-methylacrylaldehyde. Compound (I) ... ...

Abstract	Compounds (I), C22H20N2O2, (II), C22H20N2O2 and (III), C20H18N2O3 are the products of three-component reactions between isatoic anhydride, the corresponding amine and 3-(5-methylfuran-2-yl)- or (furan-2-yl)-2-methylacrylaldehyde. Compound (I) crystallizes in the monoclinic space group P21/n, while compounds (II) and (III) are isostructural and crystallize in the orthorhombic space group Pbca. The tetrahydropyrimidine ring in (I)–(III) adopts a sofa conformation. The NH nitrogen atom has a trigonal–pyramidal geometry, whereas the N(R) nitrogen atom is flattened. The furyl-vinyl substituents in (I)–(III) are practically planar and have an E configuration at the C=C double bond. In (I), this bulky fragment occupies the axial position at the quaternary carbon atom of the tetrahydropyrimidine ring, whereas in (II) and (III) it is equatorially disposed. In the crystal of (I), molecules form hydrogen-bonded chains propagating along [001] by strong intermolecular N—H.O hydrogen bonds. The chains are packed in stacks along the a-axis direction. In the crystals of (II) and (III), molecules also form hydrogen-bonded chains propagating along [100] by strong intermolecular N—H.O hydrogen bonds. However, despite the fact that compounds (II) and (III) are isostructural, steric differences between the phenyl and furyl substituents result in chains with different geometries. Thus in the crystal of (II) the chains have a zigzag-like structure, whereas in the crystal of (III), they are almost linear. In both (II) and (III), the hydrogen-bonded chains are further packed in stacks along the b-axis direction.
Keywords	furans ; quinazolinones ; acid anhydrides ; three-component reaction ; crystal structure ; synchrotron radiation ; Chemistry ; QD1-999
Subject code	540
Language	English
Publishing date	2018-08-01T00:00:00Z
Publisher	International Union of Crystallography
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Crystal strucutre of rac-methyl (11aR,12S,13R,15aS,15bS*)-11-oxo-11,11a,12,13-tetrahydro-9H,15bH-13,15a-epoxyisoindolo[1,2-c]pyrrolo[1,2-a][1,4]benzodiazepine-12-carboxylate

Vladimir P. Zaytsev / Daria N. Orlova / Atash V. Gurbanov / Fedor I. Zubkov / Victor N. Khrustalev

Acta Crystallographica Section E, Vol 70, Iss 12, Pp o1225-o

2014 Volume 1226

Abstract: The title compound, C21H18N2O4, obtained as a racemate, contains a novel heterocyclic system, viz. isoindolo[1,2-c]pyrrolo[1,2-a][1,4]benzodiazepine. The central diazepane ring has a distorted boat conformation with two phenylene-fused and one methine C ... ...

Abstract	The title compound, C21H18N2O4, obtained as a racemate, contains a novel heterocyclic system, viz. isoindolo[1,2-c]pyrrolo[1,2-a][1,4]benzodiazepine. The central diazepane ring has a distorted boat conformation with two phenylene-fused and one methine C atom deviating by 0.931 (1), 0.887 (1) and 0.561 (1) Å, respectively, from the mean plane of the rest of the ring. The γ-lactone ring has an envelope conformation, with the C atom opposite to amide bond deviating by 0.355 (1) Å from its plane. In the crystal, molecules form centrosymmetric dimers through pairs of C—H.O hydrogen bonds.
Keywords	crystals structure ; isoindolylpyrroles ; benzodiazepines ; IMDAF reaction ; hydrogen bonds ; Chemistry ; QD1-999
Language	English
Publishing date	2014-12-01T00:00:00Z
Publisher	International Union of Crystallography
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article: First example of the cascade acylation/IMDAV/ene reaction sequence, leading to N-arylbenzo[f]isoindole-4-carboxylic acids possessing anti-viral activity

Voronov, Alexander A / Kseniia A. Alekseeva / Elena A. Ryzhkova / Vladimir V. Zarubaev / Anastasia V. Galochkina / Vladimir P. Zaytsev / Mahesh S. Majik / Santosh G. Tilve / Atash V. Gurbanov / Fedor I. Zubkov

Tetrahedron letters. 2018 Mar. 21, v. 59, no. 12

2018

Abstract: The reaction between readily accessible N-aryl-3-phenylallylamines and maleic anhydride led to unexpected products – polysubstituted hydrogenated benzo[f]isoindole-4-carboxylic acids. This transformation proceeds through a previously unknown sequence of ... ...

Abstract	The reaction between readily accessible N-aryl-3-phenylallylamines and maleic anhydride led to unexpected products – polysubstituted hydrogenated benzo[f]isoindole-4-carboxylic acids. This transformation proceeds through a previously unknown sequence of steps: N-acylation of the allylamine with maleic anhydride, intramolecular Diels-Alder reaction of the vinylarene in the intermediate N-maleamide, and Alder-ene reaction of the products of the previous two steps. Selected benzo[f]isoindoles displayed antiviral activity.
Keywords	acylation ; antiviral properties ; carboxylic acids ; chemical structure ; maleic anhydrides
Language	English
Dates of publication	2018-0321
Size	p. 1108-1111.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	204287-3
ISSN	1873-3581 ; 0040-4039
ISSN (online)	1873-3581
ISSN	0040-4039
DOI	10.1016/j.tetlet.2018.02.015
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: rac-Methyl (3aR,4S,5R,7aR)-5,7a-bis(acetyloxy)-3-oxo-2-phenyloctahydro-1H-isoindole-4-carboxylate

Flavien A. A. Toze / Eugeniya V. Nikitina / Vladimir P. Zaytsev / Fedor I. Zubkov / Victor N. Khrustalev

Acta Crystallographica Section E, Vol 69, Iss 10, Pp o1555-o

2013 Volume 1555

Abstract: The title molecule, C20H23NO7, the product of nucleophilic cleavage of the 3a,6-epoxy bridge in 1-oxo-2-phenyloctahydro-3a,6-epoxyisoindole-7-carboxylate, comprises a cis-fused bicyclic system containing a 2-pyrrolidinone ring in an envelope conformation ...

Abstract	The title molecule, C20H23NO7, the product of nucleophilic cleavage of the 3a,6-epoxy bridge in 1-oxo-2-phenyloctahydro-3a,6-epoxyisoindole-7-carboxylate, comprises a cis-fused bicyclic system containing a 2-pyrrolidinone ring in an envelope conformation (with the C atom bearing the carboxylate substituent as the flap) and a cyclohexane ring in a chair conformation. The carboxylate substituent occupies the equatorial position, whereas the two acetyloxy substituents are in axial positions. The N atom has a trigonal-planar geometry, the sum of the bond angles being 359.3 (3)°. The dihedral angle between the mean plane of the four planar atoms of the pyrrolidinone ring and the phenyl ring is 25.98 (6)°. In the crystal, molecules are linked into zigzag chains along the c-axis direction by C—H.O hydrogen bonds.
Keywords	Chemistry ; QD1-999
Language	English
Publishing date	2013-10-01T00:00:00Z
Publisher	International Union of Crystallography
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article: The Intramolecular Diels-Alder Vinylthiophen (IMDAV) Reaction: an Easy Approach to Thieno[2,3-f]isoindole-4-carboxylic Acids

Horak, Yuriy I / Roman Z. Lytvyn / Yevhen-Oleh V. Laba / Yuriy V. Homza / Vladimir P. Zaytsev / Maryana A. Nadirova / Tatiana V. Nikanorova / Fedor I. Zubkov / Alexey V. Varlamov / Mykola D. Obushak

Tetrahedron letters. 2017,

2017

Abstract: The reaction of readily accessible 3-(thien-2-yl)allylamines with maleic anhydride, followed by a domino sequence involving successive acylation / [4+2] cycloaddition steps, leads to the formation of the thieno[2,3-f]isoindole core. The key step, the ... ...

Abstract	The reaction of readily accessible 3-(thien-2-yl)allylamines with maleic anhydride, followed by a domino sequence involving successive acylation / [4+2] cycloaddition steps, leads to the formation of the thieno[2,3-f]isoindole core. The key step, the intramolecular Diels-Alder vinylaren (IMDAV) reaction, proceeds with high level of diastereoselectivity and with formation of a single diastereoisomer of the target product 4,4a,5,6,7,7a-hexahydro-3aH-thieno[2,3-f]isoindole-4-carboxylic acids in excellent yields. If the reaction is carried out at room temperature, it occurs in 2-3 days and the proton migration (H-shift) does not take place at the last stage. In boiling benzene, the reaction is complete after three hours, but in this case a slight impurity of byproducts bearing aromatic thiophene ring - 4a,5,6,7,7a,8-hexahydro-4H-thieno[2,3-f]isoindole-4-carboxylic acids is formed.
Keywords	acylation ; ambient temperature ; benzene ; boiling ; byproducts ; carboxylic acids ; chemical structure ; cycloaddition reactions ; maleic anhydrides ; thiophene
Language	English
Size	p. .
Publishing place	Elsevier Ltd
Document type	Article
Note	Pre-press version
ZDB-ID	204287-3
ISSN	1873-3581 ; 0040-4039
ISSN (online)	1873-3581
ISSN	0040-4039
DOI	10.1016/j.tetlet.2017.09.038
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Article: General synthetic approach towards annelated 3a,6-epoxyisoindoles by tandem acylation/IMDAF reaction of furylazaheterocycles. Scope and limitations

Zubkov, Fedor I / Alexey V. Varlamov / Daria N. Orlova / Eugenia V. Nikitina / Roman A. Novikov / Timur R. Galeev / Victor N. Khrustalev / Vladimir P. Zaytsev

Tetrahedron. 2014 Feb. 25, v. 70

2014

Abstract: An efficient and versatile one-pot synthesis of 3,6a-epoxyisoindoles annelated with oxazine, oxazole, thiazine, thiazole, pyrimidine fragments and with their benzoannelated analogues is presented. The method is based on tandem N-acylation/intramolecular ... ...

Abstract	An efficient and versatile one-pot synthesis of 3,6a-epoxyisoindoles annelated with oxazine, oxazole, thiazine, thiazole, pyrimidine fragments and with their benzoannelated analogues is presented. The method is based on tandem N-acylation/intramolecular cycloaddition (the intramolecular DielsâAlder reaction of furan, IMDAF) reaction between Î±,Î²-unsaturated acid anhydrides and Î±-furyl substituted azaheterocycles. The latter can be easily prepared by condensation of diverse furfurals and 1,2- or 1,3-N,X-binucleophiles (aminoalcohols, aminothiols, diamines). The observed IMDAF reaction is stereoselective: exo-adducts are formed exclusively with large prevalence of one of the diastereoisomers. In most cases, the condensation/N-acylation/IMDAF reaction sequence may be carried out via a one-pot domino protocol. The scope and limitations of the proposed approach are thoroughly investigated. The obtained DielsâAlder adducts are attractive and useful substrates for further transformations. Fused isoindoles can be prepared from them in one-step by aromatization of the 7-oxabicyclo[2.2.1]heptene ring. Other transformations, including halogenation, ring cleavage, and WagnerâMeerwein skeletal rearrangement, are also demonstrated. The spatial structures of the obtained compounds have been established by X-ray diffraction analyses.
Keywords	acylation ; amino alcohols ; anhydrides ; cycloaddition reactions ; diamines ; diastereomers ; oxazoles ; stereochemistry ; synthesis ; thiazoles ; X-ray diffraction
Language	English
Dates of publication	2014-0225
Size	p. 1659-1690.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	204285-x
ISSN	1464-5416 ; 0040-4020 ; 0563-2064
ISSN (online)	1464-5416
ISSN	0040-4020 ; 0563-2064
DOI	10.1016/j.tet.2014.01.008
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