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1 Supplementary Information Cu(II)-Catalyzed Domino Reaction of 2H-Azirines with Diazotetramic and Diazotetronic Acids. Synthesis of 2-Substituted 2H-1,2,3-Triazoles Nikolai V. Rostovskii, a Mikhail S. Novikov, a, * Alexander F. Khlebnikov, a Sergei M. Korneev, a Dmitry S. Yufit b a Department of Chemistry, Saint-Petersburg State University, Universitetskii pr. 26, St. Petersburg, Russia b Department of Chemistry, Durham University, Durham, South Rd., DH1 3LE, UK. * Corresponding author. Fax: ; Tel: ; m.s.novikov@chem.spbu.ru List of the Contents General experimental details...2 Synthesis of 3-diazopyrrolidine-2,4-dione (1a)...2 Synthesis of 1-acetyl-3-diazopyrrolidine-2,4-dione (1b) 2 tert-butyl 3-diazo-2,4-dioxopyrrolidine-1-carboxylate (1c)..4 Synthesis of 1-acetyl-4-hydroxy-3-(4-methoxyphenyl)-1H-pyrrole-2(5H)-one (11) 4 1 H and 13 C NMR spectra of compounds 3, 4, 6, 7 and References.49 1
2 General experimental details Melting points were determined on a hot stage microscope and are uncorrected. 1 H (300 MHz), 13 C (75 MHz) NMR spectra were measured in CDCl 3 or DMSO-d 6 on a Bruker DPX 300 spectrometer and 1 H (400 MHz), 13 C (100 MHz) NMR spectra were measured in CDCl 3 or DMSO-d 6 on a Bruker Avance- 400 spectrometer. Chemical shifts (δ) are reported in ppm downfield from tetramethylsilane. Electrospray ionization mass spectra were measured on a Bruker microtof mass spectrometer. Elemental analysis was performed on a Hewlett-Packard 185B CHN-analyser. IR spectra were recorded on a Bruker TENSOR 27 spectrometer for tablets in KBr. Thin-layer chromatography (TLC) was conducted on aluminium sheets precoated with SiO 2 ALUGRAM SIL G/UV 254. Methyl 2,4- dioxopyrrolidine-3-carboxylate was synthesized according to the published procedure. 1 Synthesis of 3-diazopyrrolidine-2,4-dione (1a) To a solution, obtained after heating under reflux of a suspension of methyl 2,4-dioxopyrrolidine- 3-carboxylate (3.25 g, 20.7 mmol) in anhydrous acetonitrile (1.6 L) for 2 h, a solution of 4- acetamidobenzenesulfonyl azide (5.46 g, 27.7 mmol) in anhydrous acetonitrile (100 ml) and a solution of triethylamine (2.5 g, 24.8 mmol) in anhydrous acetonitrile (50 ml) were added at 0 С under stirring. The mixture was stirred at 0 С for 15 min and then at rt for 4 h. The solvent was removed under vacuum, and the orange solid was subjected to sublimation ( С/ torr) for 1.5 h to give 1.47 g (57%) of 3-diazopyrrolidine-2,4-dione as a light yellow solid. H (300 MHz; CDCl 3 ; Me 4 Si) 3.96 (2 Н, s, СН 2 ), 5.92 (1 Н, br. s, NH). Synthesis of 1-acetyl-3-diazopyrrolidine-2,4-dione (1b) To a solution of 3-diazopyrrolidine-2,4-dione (623 mg, 5 mmol) and acetic anhydride (815 mg, 8 mmol) in anhydrous dichloromethane (20 ml) a solution of 4-(N,N-dimethylamino)pyridine (305 mg, 2.5 mmol) in anhydrous dichloromethane (3 ml) was added dropwise at rt in 5 min. The mixture was stirred at rt for additional 2 h, washed with 0.5 N НCl solution (2 20 ml) and dried with MgSO 4. The removal of volatile components under vacuum and washing of the obtained solid with Et 2 O gave 575 mg (69%) of 1-acetyl-3-diazopyrrolidine-2,4-dione as a beige solid. Recrystallization of the solid from Et 2 O produces colorless prisms. Mp С. Found С, 43.34; H, 2.81; N, C 6 H 5 N 3 O 3 requires С, 43.12; H, 3.02; N max (KBr)/cm , 2152 (С=N), 1691 (C=O). H (300 MHz; CDCl 3 ; Me 4 Si) 2.60 (s, 3 Н, CH 3 ), 4.25 (s, 2 Н, СН 2 ). C (75 MHz; CDCl 3 ; Me 4 Si) 25.1 (CH 3 ), 52.9 (СН 2 ), 68.6 (С=N), (C=О), (С=О), (С=О). 2
3 Integral
4 tert-butyl 3-diazo-2,4-dioxopyrrolidine-1-carboxylate (1c) was prepared according to published procedure in 52% yield. 2 H (300 MHz; CDCl 3 ; Me 4 Si) 1.53 (9 Н, s, CH 3 ), 4.16 (2 Н, s, СН 2 ). C (75 MHz; CDCl 3 ; Me 4 Si) 27.9 (CH 3 ), 53.7 (СН 2 ), 68.5 (С=N), 84.2 (C-(CH 3 ) 3 ), (C=О), (С=О), (С=О) Synthesis of 1-acetyl-4-hydroxy-3-(4-methoxyphenyl)-1H-pyrrole-2(5H)-one (11) A solution of 1-acetyl-3-diazopyrrolidine-2,4-dione (116 mg, 0.69 mmol) and Rh 2 (OAc) 4 (3 mg, 0.01 mmol) in anisole (14 ml) was heated at 120 С under stirring for 30 min. Anisole was removed under vacuum and crystallization of the residue from Et 2 O gave 140 mg (82%) of 1-acetyl-4-hydroxy-3-(4-methoxyphenyl)-1H-pyrrole- 2(5H)-one 11 as a beige solid. Mp С (dec.). max (KBr)/cm , 2938, 2630, 1734 (C=O), 1605 (C=O), 1516, 1398, 1356, 1312, 1292, 1250, 1185, 1157, 1034, 984, 847. H (300 MHz; acetone-d 6 ; Me 4 Si) 2.48 (3 Н, s, CH 3 ), 3.81 (3 Н, s, CH 3 ), 4.31 (2 Н, s, СН 2 ), 6.95 (2 Н, d, J 8.7 Hz, ArH), 7.92 (2 Н, d, J 8.7 Hz, ArH). C (75 MHz; acetone-d 6 ; Me 4 Si) 24.8 (CH 3 ), 47.5 (СН 2 ), 55.5 (СH 3 ), 105.9, 114.1, 124.2, 129.8, 159.3, 168.6, 169.4, HRMS (ESI) [M + Na + ] calcd. for С 13 Н 13 NO 4 Na , found
5 Integral
6 1 H and 13 C NMR spectra of compounds 3, 4, 6, 7 and 12 (3аRS,6aRS)-6а-Hydroxy-2-(4-methyphenyl)-3а-[4-(4-methyphenyl)-2Н-1,2,3-triazol-2-yl]-3a,5,6,6аtetrahydropyrrolo[3,4-b]pyrrole-4(3Н)-one (3a). Fig. 1 X-ray structure of the solvate 3a EtOAc. 6
7 Integral
8 Integral (5RS,9RS)-3-(4-Methylphenyl)-9-[4-(4-methylphenyl)-2Н-1,2,3-trazol-2-yl]-1-oxa-4,7- diazaspiro[4.4]non-3-en-8-one (4a)
9
10 Integral (4-Methylphenyl)-9-[4-(4-methylphenyl)-2Н-1,2,3-trazol-2-yl]-1-oxa-4,7-diazaspiro[4.4]non-3-en- 8-one (4a) (diastereomeric mixture)
11 (3аRS,6aRS)-5-Acetyl-6а-hydroxy-2-(4-methylphenyl)-3а-[4-(4-methylphenyl)-2Н-1,2,3-triazol-2-yl]- 3a,5,6,6а-tetrahydropyrrolo[3.4-b]pyrrol-4(3Н)-one (3b) Fig. 2 X-ray structure of compound 3b. 11
12 Integral
13 Integral Acetyl-3-(4-methylphenyl)-9-[4-(4-methylphenyl)-2Н-1,2,3-triazol-2-yl]-1-oxa-4,7- diazaspiro[4.4]non-3-en-8-one (4b)
14
15 Integral (3аRS,6aRS)-5-Acetyl-6а-hydroxy-2-phenyl-3а-[4-phenyl-2Н-1,2,3-triazol-2-yl]-3a,5,6,6аtetrahydropyrrolo[3,4-b]pyrrol-4(3Н)-one (3c)
16
17 Integral Acetyl-3-phenyl-9-[4-phenyl-2Н-1,2,3-triazol-2-yl]-1-oxa-4,7-diazaspiro[4.4]non-3-en-8-one (4c)
18
19 (3aRS,6aRS)-5-Acetyl-6a-hydroxy-2-(4-methoxyphenyl)-3а-[4-(4-methoxyphenyl)-2Н-1,2,3-triazol-2- yl]-3a,5,6,6a-tetrahydropyrrolo[3,4-b]pyrrol-4(3н)-one (3d) 19
20 20
21 7-Acetyl-3-(4-methoxyphenyl)-9-[4-(4-methoxyphenyl)-2Н-1,2,3-triazol-2-yl]-1-oxa-4,7- diazaspiro[4.4]non-3-en-8-one (4d) 21
22 22
23 Integral tert-butyl (3аRS,6aRS)-6а-hydroxy-2-(4-methylphenyl)-3а-[4-(4-methylphenyl)-2Н-1,2,3-triazol-2- yl]-4-oxo-3a,4,6,6а-tetrahydropyrrolo[3,4-b]pyrrole-5(3н)-carboxylate (3e)
24
25 tert-butyl 3-(4-methylphenyl)-9-[4-(4-methylphenyl)-2Н-1,2,3-triazol-2-yl]-8-oxo-1-oxa-4,7-diazaspiro[4.4]non-3-ene-7-carboxylate (4e) Integral
26
27 (3аRS,6aRS)-6a-Hydroxy-5-(4-methoxybenzyl)-2-(4-methylphenyl)-3a-[4-(4-methylphenyl)-2H- 1,2,3-triazol-2-yl]- 3a,5,6,6a-tetrahydropyrrolo[3,4-b]pyrrol-4(3H)-one (3f) 27
28 28
29 7-(4-Methoxybenzyl)-3-(4-methylphenyl)-9-[(4-methylphenylyl)-2H-1,2,3-triazol-2-yl]-1-oxa-4,7- diazaspiro[4.4]non-3-en-8-one (4f) 29
30 30
31 (3аRS,6aSR)-6a-Hydroxy-2-(4-methylphenyl)-3a-[4-(4-methylphenyl)-1,2,3-triazol-2-yl]-6,6adihydro-3H-furo[3,4-b]pyrrol-4(3aH)-one (6a) Fig. 3 X-ray structure of compound 6a. 31
32 Integral
33 (5RS,9SR)-3-(4-Methylphenyl)-9-[4-(4-methylphenyl)-1,2,3-triazol-2-yl]-1,7-dioxa-4- azaspiro[4.4]non-3-en-8-one ((5RS,9SR)-7a) Fig. 4 X-ray structure of compound (5RS,9SR)-7a. 33
34 Integral Integral
35 (4-Methylphenyl)-9-[4-(4-methylphenyl)-1,2,3-triazol-2-yl]-1,7-dioxa-4-azaspiro[4.4]non-3-en-8- one (7a) (diastereomeric mixture) Integral
36 Integral (3аRS,6aSR)-6a-Hydroxy-2-phenyl-3a-(4-phenyl-1,2,3-triazol-2-yl)-6,6a-dihydro-3H-furo[3,4- b]pyrrol-4(3ah)-one (6b)
37
38 Integral Phenyl-9-(4-phenyl-1,2,3-triazol-2-yl)-1,7-dioxa-4-aza-spiro[4.4]non-3-en-8-one (7b)
39
40 Integral (3аRS,6aSR)-6a-Hydroxy-2-(4-methoxyphenyl)-3a-[4-(4-methoxyphenyl)-1,2,3-triazol-2-yl]-6,6adihydro-3H-furo[3,4-b]pyrrol-4(3aH)-one (6c)
41
42 Integral (4-Methoxyphenyl)-9-[(4-methoxyphenyl)-1,2,3-triazol-2-yl]-1,7-dioxa-4-azaspiro[4.4]non-3-en-8- one (7c)
43
44 Integral (3аRS,6aSR)-2-(4-Bromophenyl)-3а-[4-(4-bromophenyl)-1,2,3-triazole-2-yl]-6а-hydroxy--6,6a-dihydro- 3H-furo[3,4-b]pyrrol-4(3aH)-one (6d)
45
46 Integral (4-Bromophenyl)-9-[(4-bromophenyl)-1,2,3-triazol-2-yl]-1,7-dioxa-4-azaspiro[4.4]non-3-en-8-one (7d)
47
48 Integral (3аRS,6aSR)-5-Acetyl-6а-hydroxy-2-(4-methylphenyl)-3а-(4-methoxyphenyl)-3,5,6,6аtetahydropyrrolo[3,4-b]pyrrol-4(3Н)-one (12)
49 References 1 G. Lowe, H.W. Yeung, J. Chem. Soc., Perkin Trans , H.-D. Stachel, K. Zeitler, S. Dick, Liebigs Ann. 1996,
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