Transformations: New Approach to Sampagine derivatives. and Polycyclic Aromatic Amides

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1 -1- An Unexpected Rearrangement which Disassembles Alkyne Moiety Through Formal Nitrogen Atom Insertion between Two Acetylenic Carbons and Related Cascade Transformations: New Approach to Sampagine derivatives and Polycyclic Aromatic Amides Sergei F. Vasilevsky, a * Denis S. Baranov, a Victor I. Mamatyuk, b Yury V. Gatilov b and Igor V. Alabugin с* SUPPRTING INFRMATIN TABLE F CNTENTS Experimental Details S2 2D NMR and X-ray Structural Assignments.. S3-S5 NMR Spectra..S26-S17 Computational Data S18-S24

2 -2- Experimental part IR spectra of the compounds synthesized were recorded in KBr pellets. NMR spectra were recorded at MHz in (CD 3 ) 2 S and CDCl 3. Mass spectra were obtained by the direct injection method (the temperature of the ionization chamber was C, the ionization voltage, 70 ev). Merck 60 ( m) silica gel was used for the column chromatography. All yields are corrected for unreacted starting material. 1-Acetylenyl-9,10-anthraquinones. A mixture of terminal acetylene (4.5 mmol), 1- iodoanthra-9,10-quinone (4.5 mmol), CuI (0.027 mmol), PdCl 2 (PPh 3 ) 2 (0.013 mmol) and Et 3 N (12.7 mmol) in 50 ml of toluene was stirred under an argon atmosphere at 60 о С (2-4 h) The reaction mixture was cooled and filtered through alumina (25 x 30 mm) using toluene as the eluent. The solvents were evaporated in vacuo. The residue was recrystallized from toluene to give compounds 1a-c. The yield of 1-phenylethynyl-9,10-anthraquinone (1a) is 1.25 g (90%), mp C (from toluene), mp (lit) C. 1 The yield of 1-[2-(4-methoxyphenyl)ethynyl]-9,10-anthraquinone (1b) is 1.49 g (98%), mp C (from toluene), mp (lit) C. 1 The yield of 1-[2-(4-nitrophenyl)ethynyl]-9,10-anthraquinone (1c) is 1.52 g (95.6%), mp C (from toluene), mp (lit) C. 1 1 M Solution guanidine in methanol. Small pieces of sodium (2.3 g, 0.10 mol) were slowly added to dry CH 3 H (100 ml) with stirring. After sodium was dissolved completely, guanidine hydrochloride (9.55 g. 0.1 mol) was added in one portion. The resulting mixture was stirred at room temperature for 1 h, the white precipitate was filtered to provide a clear solution. The resulting 1 M solution of free guanidine in methanol can be stored in a refrigerator for several months. Reaction of 1-acetylenyl-9,10-anthraquinones with guanidine. A mixture of guanidine (19.5 mmol, 19.5 ml 1M solution in methanol) and respective anthraquinone 1a-c (3.25 mmol) in 50 ml of butanol-1 was refluxed for 18 h. Solvent was evaporated in vacuo. The mixture was purified by column chromatography on silica gel (d=25 mm, h=170 mm, elution with benzene followed by ethylacetate). Subsequent recrystallization gave pure compounds 4-7. For 1b The yield of 2-amino-3-(p-methoxybenzoyl)-7H-dibenzo[de,h]quinolin-7-one (5b) is 280 mg (35%), mp C (from benzene). HRMS, Found: m/z [M] +. C 24 H 16 N 2 3. Calcd.: М= IR, cm -1, ν: 1658, 1669 (С=О); 3365, 3460 (NH 2 ). The yield of 1-(pmethoxyphenyl)-7H-dibenzo[de,h]isoquinolin-3,7-dione 6b is 140 mg (19%), mp >360 C (from 1,4-dioxane). HRMS, Found: m/z [M] +. C 23 H 15 N 3. Calcd.: М= IR, cm -1, ν: 1640,1668 (С=О); 3033 (NH). For 1c - the yield of 1-(p-aminophenylethynyl)-9,10-anthraquinone 7 is 140 mg (14%), mp C (from benzene). HRMS, Found: m/z [M]+. C 22 H 13 N 2. Calcd.: М= IR, cm-1, ν: 1670 (С=О); 2187 (С С); 3352, 3441 (NH2). The yield of 1-(n-nitrophenyl)-7Hdibenzo[de,h]isoquinolin-3,7-dione (8) is 400 mg (42.5%), mp >360 C (from 1,4-dioxane). HRMS, Found: m/z [M] +. C 22 H 12 N 2 4. Calcd.: М= IR, cm-1, ν: 1642, 1666 (С=О); 3050 (NH). 1 Moroz, A. A.; Piskunov, A. V.; Shvartsberg, M. S. Bull. Acad. Sci. USSR Div. Shem. Sci. (Engl.) 1981, 30, 304.

3 -3- Structural Assignments: From the CSYDQF spectra, one can unambiguously determine the four-spin H8-H11 system (see Table S2 for the numeration). HMBC correlation of H8 with the carbonyl carbon C7 provides full assignment for each atom in this system. Assignments in the three-spin H4-H6 system are unambiguously provided by correlations of H6 and H4 with the respective C7 and C3 carbonyls. Hydrogen atoms of the phenyl group are assigned based on their intensities and HMBC vicinal correlations. Direct 13 С- 1 Н HSQC correlations confirm assignments for the C-H moieties. The fact that HMBC correlations in benzenoid structures are usually observed through vicinal spin-spin interaction allowed the assignment of other substituted and bridgehead carbons. IR-spectrum of 5a displays bands corresponding to valence stretches of NH 2 but lacks those which correspond to the presence of the С С moiety. The С 23 Н 14 N 2 О 2 composition was confirmed by high-resolution mass-spectrometry. 1 H NMR spectrum displayed only aromatic hydrogens and two hydrogens of the NH 2 group. The combination of analytical and spectra data, including the 2D-NMR analysis, allows one to assign the 2-amino-3-benzoyl-7Hdibenzo[de,h]quinolin-7-one structure for compound 5a. IR-spectrum of compound 6c indicated absence of valence stretches of either the triple bond or the NH 2 moiety whereas the 1 H NMR spectrum displayed the two four-spin systems corresponding to H8-H11 and p-substituted aromatic ring, the three-spin system corresponding to H4-H6 and broad singlet for the N-H hydrogen. 13 C NMR indicated presence of a single carbonyl group at ppm (C7) along with the characteristic amide resonance at ppm (C3). NMR assignments in this compound correlate closely with the 2D-NMR data for compound 6a with a correction for the effect of N 2 -substititution. High-resolution mass-spec data confirmed the С 22 Н 12 N 2 О 4 composition which along with the 13 C and 1 H NMR data unambiguously established compound 6c as 1-(p-nitrophenyl)-7H-dibenzo[de,h]isoquinolin-3,7-dione. Table S1. 1 Н and 13 С NMR-spectra of products of interaction 1-acetylenyl-9,10-anthraquinones with guanidine Entry 1* Compounds NH N 11 11a 11c 11b 5 7a 6a a o- i a o- 4 m- m- p- o- i- H 2 N m- 1 o a 11a 11c 10 11b a 6a m- p- 1 H Chemical Shifts (correlation with carbon atoms in (CD 3 ) 2 S) Н-4, 7.52 (C-4; C-6, C-3, C-11c) Н-5, 7.45 (C-5; C-3a, C-6a) Н-6, 8.24 (C-6; C-4, C-11c, C-7) Н-8, 8.37 (C-8; C-7, C-10, C-11a) Н-9, 7.66 (C-9; C-7a, C-11) Н-10, 7.77 (C-10; C-8, C-11a) Н-11, 8.81(C-11; C-9, C-7a, C-11b) NH 2, 5.95 (C-2, C-3) H o, 7.71 (C o ; C-12,C p ) H m, 7.41 (C m ; C i ) H p, 7.56 (C p ; C o ) Н-4, 8.65 (C-4; C-6, C-11c) Н-5, 7.86 (C-5; C-3a, C-6a) Н-6, 8.70 (C-6; C-7. C-4, C-11c) Н-8, 8.25 (C-8; C-7, C-10, C-11a) Н-9, 7.35 (C-9; C-7a, C-11) 13 C Chemical Shifts a) in (CD 3 ) 2 S C-4, C-5, C-6, C-8, C-9, C-10, C-11, C o, C m, C p, C-4, C-5, C-6, C-8, C-9, C Chemical Shifts b) in (CD 3 ) 2 S C-2, C-3, C-3a, C-11c, C-6a, C-7, C-7a, C-11a, C-11b, C-12, C i, C-7, C-3, C-1, C-11a, C-11c, 134.6

4 -4-3* a 7a 1 N 7 11b Me p N m m p- o- 6a NH 2 11c m a 6a 2 6 5b 10a 10 o- m o- 11a 7a i a 6b 7 o- 11a 7a i- 1 m- o b 9 9a 7 1 4a 11b 4 5 o- i- H 2 N 11c 6a NH 2 4 p- i- 1 H 2 N 11c 6a o- m- 3 3a 3 m- o a m- p-me Н-10, 7.19 (C-10; C-8, C-11a) Н-11, 6.81 (C-11; C-9, C-7a) NH, H o, H m, H p, H o, (C o ; C-1, C p ), H m, (C m ; C i ), H p, ( C p ; C o ) Н-4, 7.63 Н-5, 7.51 Н-6, 8.29 Н-8, 8.4 Н-9, 7.67 Н-10, 7.8 Н-11, 8.83 H-13, 3.86 NH 2, 5.61 H o, 7.75 H m, 6.9 Н-4, H-6, 8.67 Н-5, 7.85 Н-8, 8.25 Н-9, 7.35 Н-10, 7.26 Н-11, 6.94 H-12, 3.87 H o, 7.50 H m, 7.12 NH, H-3, 7.86 H-4, 8.25 H-5, H-8, H-2, H-6, H-7, H o, 7.36 H m, 6.63 NH 2, 5.74 Н-4, 8.67 Н-5, 7.89 Н-6, 8.70 Н-8, 8.26 Н-9, 7.39 Н-10, 7.29 C-10, C-11, C o, C m, C p, C-4, C-5, C-6, C-8, C-9, C-10, C-11, C-13, C o, C m, C-4, C-5, C-6, C-8, C-9, C-10, C-11, C-12, C o, C m, C-2, C-3, C-6, C-7, 134.7, 134.1, C-4,C-5,C-8, 126.9, 126.4, C o, C m, C-4, C-5, C-6, C-8, C-9, C-10, C-7a, C-6a, C-3a, C-11b, C i, C-2, C-3, C-3a, C-11c, C-6a, C-7, C-7a, C-11a, C-11b, C-12, C i, C p, C-7, C-3, C-1, C-11a, C-11c, C-7a, C-6a, C-3a, C-11b, C i, C p, C-9, C-10, 182.4, C-4a, C-8a, C-9a, C-10a, 134.2,133.9, 132.4, C-1, C-11, 87.7 C-12, 98.2 C p, C i, C-7, C-3, C-1, C-11a, C-11c, C-7a, 130.4

5 6c Н-11, 6.80 NH, H o 7.92 H m, a) For the СН carbons b) For the carbon atoms without directly attached hydrogens *) Spectrum in CDCl 3 C-11, C o, C m, C-6a, C-3a, C-11b, C i, C p, X-ray Crystallography: The single-crystal X-ray structure determination was carried out on a Bruker P4 diffractometer using Mo Kα ( Å ) radiation. An empirical absorption correction was applied by measuring 9 azimuthal scan curves. The structure was solved by direct methods and refined by full-matrix least-squares against F 2 of all data using SHELX-97 software. 2 All non-hydrogen atoms were refined anisotropically, H atoms were refined isotropically. Crystallographic data and refinement parameters for compound 6: C 22 H 13 N 2, M = , crystal size mm, monoclinic space group P2 1 /c, a = (15) Å, b = (16) Å, c = (14) Å, β = (9), V = (3) Å 3, Z = 4, ρ calcd. = g cm 3, µ = mm 1, 2θ < 26.0, T = 295(2) K. Reflections: 3673 collected, 3111 unique (R int = ), 1878 observed [I > 2σ(I)]; 279 parameters refined with R = [I > 2σ(I)], wr 2 = (all data), Gof = 1.035, residual electron density: , e Å 3. Figure 1. Structure of compound 6a (RTEP, 30% probability). Selected bond lengths, Å: C1-N (2), C1-C11B 1.376(3), N2-C (3), 1-C (2), C3A-C (3), C3A-C11C 1.413(3), C11C-C11B 1.442(3), C11B-C11A 1.490(3), 2-C (2), C6A-C (3), C7A-C (3). 2 Sheldrick, G. M. SHELX-97- Programs for Crystal Structure Analysis (release 97.2); Gottingen University: Gottingen, Germany.

6 -6- NMR Spectra: NH 2 N Ph 5a

7 -7- NH 2 N Ph 5a

8 -8-7

9 -9-5b

10 -10-5b

11 -11-6a

12 -12-6a

13 -13-6b

14 -14-6b

15 -15-6c

16 6c -16-

17 -17-7

18 -18- Geometries and energies for compounds 1a-c and selected intermediates in the proposed mechanism for the formation of products 6a-c at the B3LYP/6-31G(d,p) level 1a, R=H: HF= Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z b, R=Me: HF=

19 -19- Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z c, R=N 2 : HF= Standard orientation: Center Atomic Atomic Coordinates (Angstroms)

20 -20- Number Number Type X Y Z

21 -21- HN NH Ph 2 HN H HF= Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z

22 HN NH 2 HN Ph HF= Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z

23 HN HN Ph NH 2 HF= Input orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z

24

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