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Unusual formation of (E)-11-(amino­methyl­ene)-8,9,10,11-tetra­hydro­pyrido[2′,3′:4,5]pyrimido[1,2-a]azepin-5(7H)-one and its crystal structure

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aS.Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences of, Uzbekistan Mirzo Ulugbek Str., 77, Tashkent 100170, Uzbekistan
*Correspondence e-mail: kk_turgunov@rambler.ru

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 29 August 2017; accepted 13 September 2017; online 19 September 2017)

Selective C-formyl­ation of 8,9,10,11-tetra­hydro­pyrido[2′,3′:4,5]pyrimido[1,2-a]-azepin-5(7H)-one has been studied for the first time. It was revealed that formyl­ation proceeds by the formation of an inter­mediate salt, which due to the re-amination process on treatment with aqueous ammonia transformed into the corresponding (E)-11-(amino­methyl­ene)-8,9,10,11-tetra­hydro­pyrido[2′,3′:4,5]-pyrimido[1,2-a]azepin-5(7H)-one, C13H14N4O, as an E-isomer. Formyl­ation was carried out by Vilsmeier–Haack reagent and the structure of the synthesized compound was confirmed by X-ray structural analysis, spectroscopic and LC–MS methods. In the mol­ecule, the seven-membered penta­methyl­ene ring adopts a twist-boat conformation.

1. Chemical context

Pyrimidine-containing heterocyclic compounds are widely distributed in nature (Lagoja, 2005[Lagoja, I. M. (2005). Chem. Biodivers. 2, 1-50.]) and among synthetic compounds (Joshi et al., 2016[Joshi, G., Nayyar, H., Marin Alex, J. S., Vishwakarma, G. S., Mittal, S. & Kumar, R. (2016). Curr. Top. Med. Chem. 16, 3175-3210.]; Roopan & Sompalle, 2016[Roopan, S. M. & Sompalle, R. (2016). Syn. Commun. 46, 645-672.]). These compounds are of theoretical and practical inter­est, having plural reactivity and with many prospective biologically active compounds among the synthesized derivatives.

In previous reports we have described several syntheses, viz. the reaction of 2,3-tri­methyl­enepyrido[2,3-d]pyrimidin-4-one with aromatic aldehydes (Khodjaniyazov, 2015a[Khodjaniyazov, Kh. U. (2015a). J. Adv. Chem. 11, 3873-3875.],b[Khodjaniyazov, Kh. U. (2015b). Uzb. Chem. J. 22-25.]; Khodjaniyazov & Ashurov, 2016[Khodjaniyazov, Kh. U. & Ashurov, J. M. (2016). Acta Cryst. E72, 452-455.]), selective reduction with sodium borohydride (Khodjaniyazov et al., 2016b[Khodjaniyazov, Kh. U., Mamadrakhimov, A. A., Tadjimukhamedov, Kh. S. & Levkovich, M. G. (2016b). J. Basic Appl. Res. 2, 82-85.]), and the formation of (E)-9-(N,N-di­methyl­amino­methyl­idene)-8,9-di­hydro­pyrido[2,3-d]pyrrolo­[1,2-a]pyrimidin-5(7H)-one (Kho­djaniyazov et al., 2016a[Khodjaniyazov, Kh. U., Makhmudov, U. S. & Kutlimuratov, N. M. (2016a). J. Basic Appl. Res. 2, 382-385.]). In this current report we present the results of reaction of 8,9,10,11-tetra­hydro­pyrido[2′,3′:4,5]pyrimido[1,2-a]azepin-5(7H)-one (1) with the Vilsmeier–Haack reagent, decomposition by water and subsequent treatment with aqueous ammonia. We carried out the inter­action of 1 with a formyl­ating agent and, at the end of the reaction, the unusual final product (E)-11-(amino­methyl­ene)-8,9,10,11-tetra­hydro­pyrido[2′,3′:4,5]pyrimido-[1,2-a]azepin-5(7H)-one (3) was isolated after treatment (re-amination) of 11-di­methyl­amino­methyl­idene derivative (2) with aqueous ammonia. The reaction proceeds as shown in Fig. 1[link]. The reaction product was different from that obtained in the case of formyl­ation of 2,3-tri­methyl­ene­pyrido[2,3-d]pyrimidin-4-one [pyrido[2,3-d]pyrrolo­[1,2-a]pyrimidin-5(7H)-one; Khodjaniyazov et al., 2016a[Khodjaniyazov, Kh. U., Makhmudov, U. S. & Kutlimuratov, N. M. (2016a). J. Basic Appl. Res. 2, 382-385.]]. This fact was explained by re-amination of the initially formed di­methyl­amino­methyl­idene derivative 2 under action of aqueous ammonia to give (E)-11-(amino­methyl­ene)-8,9,10,11-tetra­hydro­pyrido[2′,3′:4,5]pyrimido[1,2-a]azepin-5(7H)-one (3) as the final product

[Scheme 1]
.
[Figure 1]
Figure 1
Reaction scheme.

2. Structural commentary

The title compound crystallizes in the centrosymmetric monoclinic P21/c (No. 14) space group. The asymmetric unit contains one crystallographically independent mol­ecule. A displacement ellipsoid plot showing the atom-numbering scheme is presented in Fig. 2[link]. In the mol­ecule, the seven-membered penta­methyl­ene ring exhibits a twist-boat conformation and has an approximate twofold symmetry with a C2 axis passing through atom C12 and midpoint of the C2—C9 bond. The amino group is E-oriented and hybridization of the N atom in this group lies between sp3 and sp2. The C—N bond makes an angle of 155° with the bis­ector of the H—N—H angle. The equivalent angle in methyl­amine with a pyramidal sp3-hybridized N atom is ∼123° (Klingebiel et al., 2002[Klingebiel, U., Neugebauer, P., Müller, I., Noltemeyer, M. & Usón, I. (2002). Eur. J. Inorg. Chem. pp. 717-722.]) and it is nearly 180° in formamide with a planar sp2-hybridized N atom (Gajda & Katrusiak, 2011[Gajda, R. & Katrusiak, A. (2011). Cryst. Growth Des. 11, 4768-4774.]). The pyrimidine ring is twisted slightly, which may be because of the influence of the twisted seven-membered azepane ring. The N1—C8A—N4A—C4 torsion angle of is 8.7 (4)°.

[Figure 2]
Figure 2
The mol­ecular structure of compound 3, with the atom labelling and 50% probability displacement ellipsoids.

3. Supra­molecular features

In the crystal, hydrogen bonds with 16 ring and three chain motifs are generated by N—H⋯N and N—H⋯O contacts (Table 1[link]). The amino group is located close to the nitro­gen atoms N1 and N8 of an inversion-related mol­ecule, forming hydrogen bonds with R12(4) and R22(12) graph-set motifs (Fig. 3[link]). This amino group also forms a hydrogen bond with the C=O oxygen atom of a mol­ecule translated along the a axis, which links the mol­ecules into R44(16) rings. Hydrogen-bonded chains are formed along [100] by alternating R22(12) and R44(16) rings (Fig. 4[link]). These chains are stabilized by inter­molecular π-π-stacking inter­actions observed between the pyridine and pyrimidine rings [centroid–centroid distance = 3.669 (2) Å; symmetry operation 1 − x, 1 − y, 1 − z].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N15—H1⋯O1i 0.85 (3) 2.21 (3) 3.017 (3) 159 (3)
N15—H2⋯N1ii 0.85 (5) 2.31 (5) 3.146 (3) 168 (4)
N15—H2⋯N8ii 0.85 (5) 2.79 (5) 3.401 (4) 131 (4)
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z+1.
[Figure 3]
Figure 3
Hydrogen bonding in the title compound showing the R12(4) and R22(12) graph-set motifs.
[Figure 4]
Figure 4
Hydrogen-bonded chain formation in 3.

4. Database survey

A search of the Cambridge Structural Database (Version 5.38, last update November 2016; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) for the 4-aza­quinazoline moiety gave eight hits. Only one of these is a related structure, a tricyclic 4-aza­quinazolin-4-one with a substituent on the third ring (VAMBET; Khodjaniyazov & Ashurov, 2016[Khodjaniyazov, Kh. U. & Ashurov, J. M. (2016). Acta Cryst. E72, 452-455.]).

5. Synthesis and crystallization

Materials and methods. The results of electro spray ionization mass spectrometry (ESI–MS) were recorded using a 6420 TripleQuadLC/MC (Agilent Technologies, US) LC–MS spectrometer. The measurements were carried out in positive-ion mode. 1H NMR spectra were recorded in CD3OD on a Varian 400-MR spectrometer operating accordingly at 400 MHz. Hexa­methyl­disiloxcane (HMDSO) was used as inter­nal standard and the chemical shift of 1H was recorded in ppm. Melting points were measured on a Boetius and MEL–TEMP apparatus manufactured by Branstead inter­national (USA) and are uncorrected. IR spectra were recorded on an IR Fourier System 2000 (Perkin–Elmer) as KBr pellets.

The reaction process was monitored by TLC on Silufol UV-254 plates using a CHCl3/CH3OH (12:1) solvent system and the developed plates were visualized under a UV lamp. Solvents were purified by standard procedures. Organic solutions were dried over anhydrous Na2SO4 or with dried CaCl2.

Synthesis of (E)-11-(amino­methyl­ene)-8,9,10,11-tetra­hydro­pyrido[2′,3′:4,5]-pyrimido[1,2-a]azepin-5(7H)-one (3). A round-bottom flask with freshly distilled DMF (3 ml, 39 mmol) was cooled by an ice–water bath and POCl3 (1 ml, 10.7 mmol) was added dropwise. The mixture was stirred (30 min), then 8,9,10,11-tetra­hydro­pyrido[2′,3′:4,5]pyrim­ido[1,2-a]azepin-5(7H)-one (1) (0.51 g, 2.4 mmol) was added into the reaction mixture. The reaction mixture was heated in a water bath for 1.5 h at 343 K and left for another day. Water (4 ml) was poured into the flask. TLC monitoring showed that the initial compound had fully transformed. The reaction mixture was treated by aqueous ammonia solution up to pH 9. The obtained solution was extracted by chloro­form (30 mL) three times. The chloro­form part was dried over Na2SO4 and the solvent was removed. Yield 0.34 g (60%), m.p. 458–460 K, Rf 0.63. Single crystals of 3 were grown from acetone solution by slow evaporation of the solvent at room temperature.

UV spectrum (ethanol, λmax, nm) neutral medium: 279.58, 348.97; acidic medium (HCl): 280.24, 362.37, 420.80; neutralization (HCl+NaOH): 279.12, 318.11, 362.29; basic medium (NaOH): 275.83, 347.71. IR spectrum (KBr, ν, cm−1): 3382 (NH2), 3325, 3203, 3064, 2924, 2869, 2824, 1642, 1613 (NH), 1591, 1562, 1523, 1470, 1433, 1389, 1353, 1319, 1267, 1249, 1227, 1184, 1126, 1107, 1077, 1045, 976, 934, 864, 825, 783, 735, 688, 663, 601, 548, 420. LC–MS (+ESI): 243 [M+H]+, 216.1, 201.1, 174, 160.9, 148.0, 121.0, 93.0, 79.0, 55.1, 39.1. 1H NMR spectrum [400 MHz, CD3OD, δ, ppm, J (Hz]): 1.77 (2H, m, γ-CH2), 1.92 (2H, m, δ-CH2), 2.385 (2H, m, β-CH2), 4.195 (2H, t, J = 6.1, -CH2), 7.454 (1H, br s, =CH), 7.28 (1H, dd, J = 4.6, 7.9, H-6), 8.45 (1H, dd, J = 7.9, 2.1, H-5), 8.735 (1H, dd, J = 4.6, 2.1, H-7).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. H-bound N atoms were freely refined. C-bound H atoms were refined as riding with C—H = 0.93 or 0.97 Å and Uiso(H) = 1.2Ueq(C).

Table 2
Experimental details

Crystal data
Chemical formula C13H14N4O
Mr 242.28
Crystal system, space group Monoclinic, P21/c
Temperature (K) 293
a, b, c (Å) 8.7260 (7), 15.236 (3), 8.6642 (7)
β (°) 98.046 (8)
V3) 1140.6 (3)
Z 4
Radiation type Cu Kα
μ (mm−1) 0.76
Crystal size (mm) 0.40 × 0.35 × 0.15
 
Data collection
Diffractometer Oxford Diffraction Xcalibur, Ruby
Absorption correction Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007[Oxford Diffraction. (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.])
Tmin, Tmax 0.965, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 7589, 2328, 1478
Rint 0.059
(sin θ/λ)max−1) 0.631
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.141, 1.04
No. of reflections 2328
No. of parameters 171
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.18, −0.20
Computer programs: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction. (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]), SHELXS7 and XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and SHELXL2014/7 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]).

Supporting information


Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS7 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015).

(E)-11-(Aminomethylene)-8,9,10,11-tetrahydropyrido[2',3':4,5]pyrimido[1,2-a]azepin-5(7H)-one top
Crystal data top
C13H14N4ODx = 1.411 Mg m3
Mr = 242.28Melting point: 458(2) K
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 8.7260 (7) ÅCell parameters from 911 reflections
b = 15.236 (3) Åθ = 5.9–75.7°
c = 8.6642 (7) ŵ = 0.76 mm1
β = 98.046 (8)°T = 293 K
V = 1140.6 (3) Å3Plate, colourless
Z = 40.40 × 0.35 × 0.15 mm
F(000) = 512
Data collection top
Oxford Diffraction Xcalibur, Ruby
diffractometer
2328 independent reflections
Radiation source: Enhance (Cu) X-ray Source1478 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
Detector resolution: 10.2576 pixels mm-1θmax = 76.7°, θmin = 5.1°
ω scansh = 910
Absorption correction: multi-scan
(CrysAlis Pro; Oxford Diffraction, 2007)
k = 1918
Tmin = 0.965, Tmax = 1.000l = 108
7589 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141 w = 1/[σ2(Fo2) + (0.0554P)2 + 0.003P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2328 reflectionsΔρmax = 0.18 e Å3
171 parametersΔρmin = 0.20 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6098 (2)0.35990 (15)0.1710 (2)0.0621 (5)
N30.3638 (2)0.39263 (13)0.2102 (2)0.0449 (4)
N10.2921 (2)0.40925 (14)0.4621 (2)0.0472 (5)
N80.4731 (3)0.39670 (16)0.6821 (2)0.0569 (5)
N150.1422 (3)0.49351 (19)0.2758 (3)0.0606 (6)
C20.2547 (3)0.40679 (15)0.3099 (3)0.0438 (5)
C90.0935 (3)0.41797 (17)0.2412 (3)0.0478 (5)
C4A0.5549 (3)0.36809 (16)0.4323 (3)0.0468 (5)
C8A0.4417 (3)0.39271 (15)0.5243 (3)0.0459 (5)
C40.5167 (3)0.37221 (16)0.2626 (3)0.0476 (5)
C140.0100 (3)0.47631 (17)0.3123 (3)0.0491 (5)
H14A0.06300.50780.39500.059*
C130.3195 (3)0.40613 (17)0.0415 (3)0.0502 (6)
H13A0.41100.42000.00560.060*
H13B0.24920.45560.02470.060*
C50.7016 (3)0.34430 (18)0.5046 (3)0.0557 (6)
H5A0.77820.32800.44570.067*
C120.2420 (3)0.32550 (18)0.0367 (3)0.0560 (6)
H12A0.19950.34000.14320.067*
H12B0.31890.27980.04030.067*
C60.7310 (3)0.34538 (19)0.6636 (3)0.0576 (6)
H6A0.82680.32810.71540.069*
C100.0156 (3)0.3637 (2)0.1043 (3)0.0607 (7)
H10A0.07720.33740.13410.073*
H10B0.01630.40300.01770.073*
C70.6134 (3)0.3731 (2)0.7466 (3)0.0603 (6)
H7A0.63540.37500.85470.072*
C110.1136 (3)0.2911 (2)0.0480 (3)0.0617 (7)
H11A0.15890.25660.13680.074*
H11B0.04740.25270.02140.074*
H10.201 (4)0.456 (2)0.224 (4)0.112 (16)*
H20.181 (6)0.527 (3)0.338 (5)0.16 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0464 (10)0.0880 (14)0.0538 (10)0.0053 (9)0.0141 (8)0.0095 (9)
N30.0398 (10)0.0537 (11)0.0415 (10)0.0006 (8)0.0065 (8)0.0030 (8)
N10.0420 (10)0.0574 (12)0.0430 (10)0.0022 (9)0.0082 (8)0.0032 (8)
N80.0562 (13)0.0707 (14)0.0428 (11)0.0026 (10)0.0039 (9)0.0027 (9)
N150.0465 (13)0.0786 (17)0.0566 (13)0.0100 (11)0.0072 (10)0.0016 (11)
C20.0416 (12)0.0462 (12)0.0440 (12)0.0003 (9)0.0070 (9)0.0030 (9)
C90.0400 (12)0.0593 (14)0.0443 (12)0.0014 (10)0.0071 (9)0.0003 (10)
C4A0.0424 (12)0.0492 (13)0.0484 (12)0.0002 (10)0.0047 (10)0.0026 (9)
C8A0.0430 (12)0.0494 (13)0.0450 (12)0.0015 (9)0.0049 (9)0.0019 (9)
C40.0404 (12)0.0500 (12)0.0533 (13)0.0002 (10)0.0097 (10)0.0076 (10)
C140.0393 (12)0.0630 (15)0.0446 (12)0.0021 (11)0.0042 (9)0.0033 (10)
C130.0478 (13)0.0601 (15)0.0436 (12)0.0002 (11)0.0088 (10)0.0018 (10)
C50.0450 (14)0.0610 (16)0.0611 (15)0.0061 (11)0.0074 (11)0.0003 (11)
C120.0616 (16)0.0598 (16)0.0457 (13)0.0034 (12)0.0044 (11)0.0082 (10)
C60.0467 (13)0.0625 (16)0.0600 (15)0.0042 (11)0.0053 (11)0.0051 (12)
C100.0461 (14)0.0748 (18)0.0598 (16)0.0004 (13)0.0023 (11)0.0098 (13)
C70.0628 (16)0.0693 (17)0.0455 (13)0.0001 (13)0.0036 (11)0.0008 (11)
C110.0616 (17)0.0634 (17)0.0589 (16)0.0091 (13)0.0046 (12)0.0110 (12)
Geometric parameters (Å, º) top
O1—C41.227 (3)C14—H14A0.9300
N3—C41.383 (3)C13—C121.516 (4)
N3—C21.389 (3)C13—H13A0.9700
N3—C131.473 (3)C13—H13B0.9700
N1—C21.314 (3)C5—C61.365 (4)
N1—C8A1.364 (3)C5—H5A0.9300
N8—C71.323 (4)C12—C111.516 (4)
N8—C8A1.357 (3)C12—H12A0.9700
N15—C141.347 (3)C12—H12B0.9700
N15—H10.852 (19)C6—C71.398 (4)
N15—H20.849 (19)C6—H6A0.9300
C2—C91.458 (3)C10—C111.519 (4)
C9—C141.352 (3)C10—H10A0.9700
C9—C101.525 (4)C10—H10B0.9700
C4A—C51.392 (3)C7—H7A0.9300
C4A—C8A1.405 (3)C11—H11A0.9700
C4A—C41.463 (3)C11—H11B0.9700
C4—N3—C2122.98 (19)C12—C13—H13B109.3
C4—N3—C13117.70 (18)H13A—C13—H13B107.9
C2—N3—C13119.16 (19)C6—C5—C4A118.8 (2)
C2—N1—C8A118.76 (19)C6—C5—H5A120.6
C7—N8—C8A117.3 (2)C4A—C5—H5A120.6
C14—N15—H1120 (3)C11—C12—C13112.1 (2)
C14—N15—H2116 (4)C11—C12—H12A109.2
H1—N15—H2118 (4)C13—C12—H12A109.2
N1—C2—N3122.2 (2)C11—C12—H12B109.2
N1—C2—C9119.8 (2)C13—C12—H12B109.2
N3—C2—C9118.0 (2)H12A—C12—H12B107.9
C14—C9—C2116.2 (2)C5—C6—C7118.4 (2)
C14—C9—C10120.1 (2)C5—C6—H6A120.8
C2—C9—C10123.6 (2)C7—C6—H6A120.8
C5—C4A—C8A119.3 (2)C11—C10—C9115.8 (2)
C5—C4A—C4121.9 (2)C11—C10—H10A108.3
C8A—C4A—C4118.7 (2)C9—C10—H10A108.3
N8—C8A—N1115.9 (2)C11—C10—H10B108.3
N8—C8A—C4A121.6 (2)C9—C10—H10B108.3
N1—C8A—C4A122.3 (2)H10A—C10—H10B107.4
O1—C4—N3121.1 (2)N8—C7—C6124.6 (2)
O1—C4—C4A124.5 (2)N8—C7—H7A117.7
N3—C4—C4A114.40 (19)C6—C7—H7A117.7
N15—C14—C9126.7 (2)C12—C11—C10113.0 (2)
N15—C14—H14A116.6C12—C11—H11A109.0
C9—C14—H14A116.6C10—C11—H11A109.0
N3—C13—C12111.7 (2)C12—C11—H11B109.0
N3—C13—H13A109.3C10—C11—H11B109.0
C12—C13—H13A109.3H11A—C11—H11B107.8
N3—C13—H13B109.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N15—H1···O1i0.85 (3)2.21 (3)3.017 (3)159 (3)
N15—H2···N1ii0.85 (5)2.31 (5)3.146 (3)168 (4)
N15—H2···N8ii0.85 (5)2.79 (5)3.401 (4)131 (4)
Symmetry codes: (i) x1, y, z; (ii) x, y+1, z+1.
 

Funding information

The work was supported by fundamental grant FA-F7-T207 `Theoretical aspects of formation of the asymmetric centers in biologically active heterocyclic mol­ecules' from the Academy of Sciences of the Republic of Uzbekistan.

References

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