Supporting Information. Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles
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- Λυσιστράτη Τρικούπης
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1 Supporting Information for Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles Angélica de Fátima S. Barreto*, Veronica Alves dos Santos, and Carlos Kleber Z. Andrade* Address: Laboratório de Química Metodológica e rgânica Sintética, Instituto de Química, Universidade de Brasília, , Brasília-DF, Brazil Angélica de Fátima S. Barreto - angelfsb@yahoo.com.br; Carlos Kleber Z. Andrade - ckleber@unb.br *Corresponding author Detailed experimental procedures, MR and mass spectra Table of contents General Information... S2 General procedure for the Ugi-tetrazole reaction... S2 Spectra of compounds... S14 S66 S1
2 General information MR spectra were recorded on a Bruker Ascend instrument using a 5 mm internal diameter probe operating at 600 Mz for 1 and at 150 Mz for 13 C in the presence of TMS as internal standard. igh resolution ESIMS analyses were carried out on a triple TF (AB Sciex) with internal calibration and direct solution (1 ppm) infusion in positive ion mode. TLC plates were revealed by treatment with a 10% solution of phosphomolybdic acid in ethanol, followed by heating. Melting points were recorded on a Marconi melting point and are uncorrected. Commercially available reagents and solvents were of analytical grade or were purified by standard procedures prior to use. Compounds were analyzed by 1 MR, 13 C MR and high resolution ESI mass spectra giving data consistent with the proposed structures. Compounds names were given based on ChemDraw software 7.0. General procedure for the hydrazino-ugi-azide reactions: To a stirred solution of hydrazide 2a c (0.40 mmol) in TFE (1.0 ml) were added successively oxo compound 7a h (0.40 mmol, 0.80 mmol when a ketone was used), trimethylsilylazide (8, TMS azide, 0.40 mmol), methyl isocyanoacetate (9, 0.40 mmol) and ZnCl 2 (10 mol %). The resulting mixture was stirred at room temperature for 24 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography to obtain the Ugi tetrazole product. S2
3 Me 10a C 3 {5-[1-('-Acetylhydrazino)-2-methylpropyl] tetrazol-1-yl}acetic acid methyl ester (10a): Prepared following the general procedure using acetylhydrazide (2a, 0.73 mmol, g), isobutyraldehyde (7a, 0.73 mmol, g), trimethylsilyl azide (8, 0.73 mmol, g), methyl isocyanoacetate (9, 0.73 mmol, ml) and ZnCl 2 (0.073 mmol, g). Purification by column chromatography (C 2 Cl 2 2% Me/C 2 Cl 2 ) furnished product 10a in 44% yield (0.086 g, 0.32 (C 2 Cl 2 /Me 5%) mmol) as a yellow oil. R f 1 MR (600 Mz, CDCl 3 ) δ 7.47 (br s, 1), 5.39 (s, 2), 5.06 (br s, 1), 4.31 (d, J = 8.8 z, 1), 3.85 (s, 3), (m, 1), 1.88 (s, 3), 1.21 (d, J = 6.6 z, 3), 0.81 (d, J = 6.6 z, 3). 13 C MR (150 Mz, CDCl 3 ): δ 169.8, 167.6, 154.9, 63.0, 53.4, 48.8, 30.7, 20.9, 19.6, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: Me C 3 10b {5-[1-('-Acetylhydrazino)-1-methylethyl]-tetrazol- 1-yl}acetic acid methyl ester (10b): Prepared following the general procedure using acetylhydrazide (2a, 0.73 mmol, g), acetone (7b, mmol, ml), trimethylsilyl azide (8, 0.73 mmol, g), methyl isocyanoacetate (9, 0.73 mmol, ml) and ZnCl 2 (0.073 mmol, g). Purification by column chromatography (C 2 Cl 2 2% Me/C 2 Cl 2 ) furnished product 10b in 36% yield (0.067 g, 0.26 mmol) as a white solid. Mp C; R f (C 2 Cl 2 /Me 5%) MR (600 Mz, CDCl 3 ) δ 7.18 (br s, 1), 5.47 (s, 2), 4.98 (br s, 1), 3.86 (s, 3), 1.92 (s, 3), 1.63 (s, 6). 13 C MR (150 Mz, CDCl 3 ): δ 169.8, 168.2, 158.3, 57.4, 53.4, 49.7, 24.8, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: S3
4 Me C 3 1-yl}acetic acid methyl ester (10c): Prepared following the general procedure using acetylhydrazide (2a, 0.40 mmol, g), 3-pentanone (7c, 0.40 mmol, g), trimethylsilyl azide (8, 0.40 mmol, g), methyl isocyanoacetate (9, 0.40 mmol, ml) and ZnCl 2 (0.040 mmol, g). Purification by column chromatography (C 2 Cl 2 2% Me/C 2 Cl 2 ) furnished product 10c in 47% yield (0.053 g, 0.19 mmol) as a white solid. Mp C; R f (C 2 Cl 2 /Me 5%) MR (600 Mz, CDCl 3 ) δ 7.08 (br s, 1), 5.54 (s, 2), 5.26 (br s, 1), 3.84 (s, 3), (m, 2), (m, 2), 1,89 (s, 3), 0.88 (t, J = 7.0 z, 6). 13 C MR (150 Mz, CDCl 3 ): δ 169.1, 168.4, 157.2, 63.6, 53.4, 49.9, 24.9, 21.0, 7.2. RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: Me 10d C 3 10c {5-[1-('-Acetylhydrazino)-1-ethylpropyl]-tetrazol- {5-[1-('-Acetylhydrazino)-2-phenylethyl]-tetrazol- 1-yl}acetic acid methyl ester (10d): Prepared following the general procedure using acetylhydrazide (2a, 0.73 mmol, g), phenylacetaldehyde (7d, 0.73 mmol, g), trimethylsilyl azide (8, 0.73 mmol, g), methyl isocyanoacetate (9, 0.73 mmol, ml) and ZnCl 2 (0.073 mmol, g). Purification by column chromatography (C 2 Cl 2 2% Me/C 2 Cl 2 ) furnished product 10d in 30% yield (0.069 g, 0.22 mmol) as a yellow oil. R f (C 2 Cl 2 /Me 5%) MR (600 Mz, CDCl 3 ) δ 7.50 (s, 1), (m, 3), (m, 2), 4.94 and 4.91 (2s, 1, rotamers), 4.87 (t, J = 7.0 z, 1), 4.79 and 4.76 (2s, 1, rotamers), 3.79 (s, 3), (m, 2), 1.85 (s, 3). 13 C MR (150 S4
5 Mz, CDCl 3 ): δ 170.1, 167.2, 155.1, 135.0, 129.2, 128.9, 127.6, 57.1, 53.3, 48.0, 38.9, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: Me 10e C 3 yl}acetic acid methyl ester (10e): Prepared following the general procedure using acetylhydrazide (2a, 0.73 mmol, g), cyclohexanone (7e, 0.73 mmol, g), trimethylsilyl azide (8, 0.73 mmol, g), methyl isocyanoacetate (9, 0.73 mmol, ml) and ZnCl 2 (0.073 mmol, g). Purification by column chromatography (C 2 Cl 2 2% Me/C 2 Cl 2 ) furnished product 10e in 40% yield (0.093 g, 0.29 mmol) as a white solid. Mp C, R f (C 2 Cl 2 /Me 5%) MR (600 Mz, CDCl 3 ) δ 7.17 (d, J = 5.9 z, 1), 5.51 (s, 2), 5.30 (d, J = 7.3 z, 1), 3.84 (s, 3), (m, 2), 1.89 (s, 3), (m, 2), (m, 2), (m, 2), (m, 2). 13 C MR (150 Mz, CDCl 3 ): δ 169.5, 168.1, 157.6, 59.5, 53.4, 49.8, 33.1, 24.9, 21.8, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: Me 10f C 3 {5-[1-('-Acetylhydrazino)cyclohexyl]-tetrazol-1- {5-[1-('-Acetylhydrazino)cyclopentyl]-tetrazol-1- yl}acetic acid methyl ester (10f): Prepared following the general procedure using acetylhydrazide (2a, 0.73 mmol, g), cyclopentanone (7f, 0.73 mmol, 0,061 g), trimethylsilyl azide (8, 0.73 mmol, g), methyl isocyanoacetate (9, 0.73 mmol, ml) and ZnCl 2 (0.073 mmol, g). Purification by column chromatography (C 2 Cl 2 2% Me/C 2 Cl 2 ) furnished product 10f in 36% yield (0.074 g, 0.26 mmol) as a yellow solid. Mp C; R f (C 2 Cl 2 /Me 5%) S5
6 1 MR (600 Mz, CDCl 3 ) δ 7.21 (d, J = 7.5 z, 1), 5.41 (s, 2), 5.15 (d, J = 7.7 z, 1), 3.84 (s, 3), (m, 2), (m, 1), (m, 2), 1.90 (s, 3), (m, 2). 13 C MR (150 Mz, CDCl 3 ): δ 170.0, 168.1, 158.4, 67.6, 53.4, 49.3, 35.0, 27.0, 24.8, 23.9, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: Me 10g C 3 yl}acetic acid methyl ester (10g): Prepared following the general procedure using acetylhydrazide (2a; 0.40 mmol, g), cycloheptanone (7g, 0.40 mmol, g), trimethylsilyl azide (8, 0.40 mmol, g), methyl isocyanoacetate (9, 0.40 mmol, ml) and ZnCl 2 (0.040 mmol, g). Purification by column chromatography (C 2 Cl 2 2% Me/C 2 Cl 2 ) furnished product 10g in 53% yield (0,066 g, 0.21 mmol) as a white solid. Mp C; R f (C 2 Cl 2 /Me 5%) MR (600 Mz, CDCl 3 ) δ 7.17 (br s, 1), 5.49 (s, 2), 5.24 (d, J = 8.1 z, 1), 3.85 (s, 3), (m, 2), (m, 2), 1.90 (s, 3), (m, 4), (m, 4). 13 C MR (150 Mz, CDCl 3 ): δ 169.6, 168.6, 158.8, 63.8, 53.5, 49.9, 35.2, 30.4, 22.3, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: Me 10h C 3 {5-[1-('-Acetylhydrazino)cycloheptyl]-tetrazol-1- {5-[1-('-Acetyl-hydrazino)-1,3-dimethyl-butyl]- tetrazol-1-yl}-acetic acid methyl ester (10h): Prepared following the general procedure using acetylhydrazide (2a, 0.40 mmol, g), methyl isobutyl ketone (7h, 0.40 mmol, g), trimethylsilyl azide (8, 0.40 mmol, g), S6
7 methyl isocyanoacetate (9, 0.40 mmol, ml) and ZnCl 2 (0.040 mmol, g). Purification by column chromatography (C 2 Cl 2 2% Me/C 2 Cl 2 ) furnished product 10h in 47% yield (0.056 g, 019 mmol) as a white solid. Mp C; R f (C 2 Cl 2 /Me 5%) MR (600 Mz, CDCl 3 ) δ 7.15 (br s, 1), 5.54 (d, J = 17.0 z, 1), 5.38 (s, J = 17.0 z, 1), 5.03 (br s, 1), 3.86 (s, 3), 1.91 (s, 3), 1.72 (s, 3), (m, 3), 0.97 (d, J = 6.2 z, 3), 0.52 (d, J = 6.2 z, 3). 13 C MR (150 Mz, CDCl 3 ): δ 169.9, 168.4, 157.7, 60.7, 53.5, 49.7, 47.2, 24.7, 24.2, 23.2, 21.2, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: Me Cbz 10i (5-{1-['-(2-(Benzyloxycarbonylamino)acetyl)hydrazino]-1-methylethyl}-tetrazol-1-yl)acetic acid methyl ester (10i): Prepared following the general procedure using Cbz-glycine hydrazide (2b, 0.40 mmol, g), acetone (7b, 0.80 mmol, g), trimethylsilyl azide (8, 0.40 mmol, g), methyl isocyanoacetate (9, 0.40 mmol, ml) and ZnCl 2 (0.040 mmol, g). Purification by column chromatography (C 2 Cl 2 2% Me/C 2 Cl 2 ) furnished product 10i in quantitative yield (0.162 g, 0.40 mmol) as a white solid. Mp C; R f (C 2 Cl 2 /Me 5%) MR (600 Mz, CDCl 3 ) δ 7.77 (d, J = 7.4 z, 1), (m, 5), 5.47 (s, 2), 5.45 (br s, 1), 5.09 (s, 2), 4.92 (d, J = 7.4 z, 1), 3.83 (d, J = 5.9 z, 2), 3.80 (s, 3), 1.60 (s, 6). 13 C MR (150 Mz, CDCl 3 ): δ 169.1, 168.3, 158.1, 156.5, 136.0, 128.5, 128.2, 128.1, 67.2, 57.5, 53.6, 49.8, 43.3, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: S7
8 Me Boc 10j (5-{1-['-(2-(tert- Butoxycarbonylamino)acetyl)hydrazino]-1-methylethyl}-tetrazol-1-yl)acetic acid methyl ester (10j): Prepared following the general procedure using Bocglycine hydrazide (2c, 0.40 mmol, g), acetone (7b, 0.80 mmol, g), trimethylsilyl azide (8, 0.40 mmol, g), methyl isocyanoacetate (9, 0.40 mmol, ml) and ZnCl 2 (0.040 mmol, g). Purification by column chromatography (C 2 Cl 2 2% Me/C 2 Cl 2 ) furnished product 10j in 97% yield (0.144 g, 0.39 mmol) as a colorless oil. R f (C 2 Cl 2 /Me 5%) MR (600 Mz, CDCl 3 ) δ 7.72 (br s, 1), 5.47 (s, 2), 5.04 (br s, 1), 4.93 (br s, 1), 3.84 (s, 3), 3.77 (d, J = 5.9 z, 2), 1.62 (s, 6), 1.41 (s, 9). 13 C MR (150 Mz, CDCl 3 ): δ 169.6, 167.9, 158.1, 155.9, 80.2, 57.3, 53.4, 49.8, 42.9, 28.1, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: Me 10k Cbz (5-{1-['-(2- (Benzyloxycarbonylamino)acetyl)hydrazino]-cyclohexyl}-tetrazol-1- yl)acetic acid methyl ester (10k): Prepared following the general procedure using Cbz-glycine hydrazide (2b, 0.40 mmol, g), cyclohexanone (7e, 0.40 mmol, g), trimethylsilyl azide (8, 0.40 mmol, g), methyl isocyanoacetate (9, 0.40 mmol, ml) and ZnCl 2 (0.040 mmol, g). Purification by column chromatography (C 2 Cl 2 2% Me/C 2 Cl 2 ) furnished product 10k in 85% yield (0.151 g, 0.34 mmol) as a white solid. Mp C; R f (C 2 Cl 2 /Me 5%) MR (600 Mz, CDCl 3 ) δ 7.62 (br s, 1), (m, 5), 5.49 (s, 2), 5.32 (br s, 1), 5.23 (br s, 1), 5.08 (s, 2), 3.80 (s, 5), (m, 2), (m, 2), (m, 2), (m, 2), (m, 2). S8
9 13 C MR (150 Mz, CDCl 3 ): δ 168.8, 168.3, 157.5, 156.4, 136.0, 128.5, 128.2, 128.1, 67.2, 59.7, 53.6, 49.9, 43.3, 33.2, 25.0, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: Me 10l Boc (5-{1-['-(2-(tert- Butoxycarbonylamino)acetyl)hydrazino]-cyclohexyl}-tetrazol-1-yl)acetic acid methyl ester (10l): Prepared following the general procedure using Bocglycine hydrazide (2c, 0.40 mmol, g), cyclohexanone (7e, 0.40 mmol, g), trimethylsilyl azide (8, 0.40 mmol, g), methyl isocyanoacetate (9, 0.40 mmol, ml) and ZnCl 2 (0.040 mmol, g). Purification by column chromatography (C 2 Cl 2 3% Me/C 2 Cl 2 ) furnished product 10l in 57% yield (0.094 g, 0.23 mmol) as a white solid. Mp C; R f (C 2 Cl 2 /Me 5%) Me 10m Boc 1 MR (600 Mz, CDCl 3 ) δ 7.67 (s, 1), 5.50 (s, 2), 5.01 (s, 1), 3.82 (s, 3), 3.74 (s, 2), (m, 2), (m, 2), (m, 2), (m, 2), (m, 2), 1.41 (s, 9). 13 C MR (150 Mz, CDCl 3 ): δ 169.3, 168.1, 157.3, 155.8, 80.4, 59.7, 53.5, 49.9, 43.0, 33.2, 28.2, 24.9, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: (5-{1-['-(2-(tert- Butoxycarbonylamino)acetyl)hydrazino]-cycloheptyl}-tetrazol-1-yl)acetic acid methyl ester (10m): Prepared following the general procedure using Boc- S9
10 glycine hydrazide (2c, 0.40 mmol, g), cycloheptanone (7g, 0.40 mmol, g), trimethylsilyl azide (8, 0.40 mmol, g), methyl isocyanoacetate (9, 0.40 mmol, ml) and ZnCl 2 (0.040 mmol, g). Purification by column chromatography (C 2 Cl 2 4% Me/C 2 Cl 2 ) furnished product 10n in 62% yield (0.106 g, 0.25 mmol) colorless oil. R f (C 2 Cl 2 /Me 5%) MR (600 Mz, CDCl 3 ) δ 7.68 (s, 1), 5.49 (s, 2), 5.04 (s, 1), 3.83 (s, 3), 3.76 (d, J = 5.5 z, 2), (m, 2), (m, 2), (m, 8), 1.40 (s, 9). 13 C MR (150 Mz, CDCl 3 ): δ 169.3, 168.2, 158.6, 155.8, 80.3, 63.8, 53.5, 50.8, 49.9, 43.8, 35.3, 30.4, 28.2, 24.3, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: Boc {'-[1-(1-ydrazinocarbonylmethyl-1tetrazol-5-yl)-1-methylethyl]-hydrazinocarbonylmethyl}carbamic acid tertbutyl ester (11): To a solution of compound 10j (0.371 g, 1.00 mmol) in 2.0 ml of ethanol was added hydrazine hydrate (0.200 g, 4.00 mmol). After refluxing for 5 h, the residue was concentrated in vacuum and purified by column chromatography (C 2 Cl 2 10% Me/C 2 Cl 2 ) furnishing product 6 in 55% yield (0.204 g, 0.55 mmol) as a white solid. Mp C; R f (C 2 Cl 2 /Me 15%) MR (600 Mz, DMS-d 6 ) δ 9.59 (s, 1), 9.00 (d, J = 5.9 z, 1), 6.95 (t, J = 6.1 z, 1), 5.51 (s, 2), 5.37 (d, J = 5.9 z, 1), 4.39 (br, 1), 3.43 (d, J = 5.9 z, 2), 1.46 (s, 6), 1.35 (s, 9). 13 C MR (150 Mz, DMS-d 6 ): δ 169.1, 165.2, 158.3, 155.8, 78.1, 56.5, 49.5, 34.7, 28.2, 25.1, 18.6, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: S10
11 Me 12a Boc [5-(1-{'-[2-(5-{1-['-(2-(tert- Butoxycarbonylamino)acetyl)hydrazino]-1-methylethyl}-tetrazol-1- yl)acetyl]hydrazino}-cycloheptyl)-tetrazol-1-yl]acetic acid methyl ester (12a): Prepared following the general procedure using hydrazide 11 (0.13 mmol, g), cycloheptanone (7g, 0.13 mmol, g), trimethylsilyl azide (8, 0.13 mmol, g), methyl isocyanoacetate (9, 0.13 mmol, ml) and ZnCl 2 (0.013 mmol, g). Purification by column chromatography (C 2 Cl 2 4% Me/C 2 Cl 2 ) furnished product 12a in 68% yield (0.055 g, mmol) as a white solid. Mp C; R f (C 2 Cl 2 /Me 10%) MR (600 Mz, DMS-d 6 ) δ 9.59 (d, J = 4.4 z, 1), 8.94 (d, J = 5.1 z, 1), 6.88 (s, 1), 5.87 (s, 2), 5.64 (d, J = 4.4 z, 1), 5.45 (s, 2), 5.27 (d, J = 5.5 z, 1), 3.71 (s, 3), 3.39 (d, J = 5.9 z, 2), (m, 2), (m, 2), (m, 2), (m, 4), (m, 17). 13 C MR (150 Mz, DMS-d 6 ): δ 169.0, 167.6, 165.6, (2C), 155.7, 78.0, 62.4, 56.1, 54.9, 52.7, 49.6, 49.3, 45.7, 41.7, 35.0, 29.6, 28.1, 24.9, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: Me Boc 12b [5-(1-{'-[2-(5-{1-['-(2-(tert- Butoxycarbonylamino)acetyl)hydrazino]-1-methylethyl}-tetrazol-1- yl)acetyl]hydrazino}-1-ethylpropyl)-tetrazol-1-yl]acetic acid methyl ester (12b): Prepared following the general procedure using hydrazide 11 (0.35 mmol, g), 3-pentanone (7c, 0.35 mmol, g), trimethylsilyl azide (8, 0.35 mmol, g), methyl isocyanoacetate (9, 0.35 mmol, ml) and S11
12 ZnCl 2 (0.035 mmol, g). Purification by column chromatography (C 2 Cl 2 5% Me/C 2 Cl 2 ) furnished product 12b in 54% yield (0.110 g, 0.19 mmol) as a yellow solid. Mp C; R f (C 2 Cl 2 /Me 10%) MR (600 Mz, DMS-d 6 ) δ 9.47 (br s, 1), 8.95 (d, J = 5.5 z, 1), 6.88 (t, J = 6.1 z, 1), 5.93 (s, 2), 5.66 (br s, 1), 5.46 (s, 2), 5.25 (d, J = 5.5 z, 1), 3.70 (s, 3), 3.39 (d, J = 5.9 z, 2), (m, 2), (m, 2), 1.35 and 1.33 (2s, 15), 0.69 (t, J = 7.5 z, 6). 13 C MR (150 Mz, DMS-d 6 ): δ 169.0, 167.6, 165.7, 158.0, 156.4, 155.7, 78.0, 62.5, 56.0, 52.7, 49.8, 49.3, 45.7, 41.7, 28.1, 24.8, 24.7, 20.0, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: Me 12c Boc [5-(1-{'-[2-(5-{1-['-(2-(tert- Butoxycarbonylamino)acetyl)hydrazino]-1-methylethyl}-tetrazol-1- yl)acetyl]hydrazino}-cyclohexyl)-tetrazol-1-yl]acetic acid methyl ester (12c): Prepared following the general procedure using hydrazide 11 (0.26 mmol, g), cyclohexanone (7e, 0.26 mmol, g), trimethylsilyl azide (8, 0.26 mmol, g), methyl isocyanoacetate (9, 0.26 mmol, ml) and ZnCl 2 (0.026 mmol, g). Purification by column chromatography (C 2 Cl 2 4% Me/C 2 Cl 2 ) furnished product 12c in 70% yield (0.108 g, 0.18 mmol) as a yellow solid. Mp C; R f (C 2 Cl 2 /Me 10%) MR (600 Mz, DMS-d 6 ) δ 9.59 (br s,1), 8.92 (d, J = 5.3 z, 1), 6.88 (s, 1), 5.84 (s, 2), 5.67 (s, 1), 5.41 (s, 2), 5.25 (d, J = 5.3 z, 1), 3.70 (s, 3), 3.40 (d, J = 5.9 z, 2), (m, 2), (m, 2), (m, 2), (m, 4), 1.35 and 1.33 (2s, 15). 13 C MR (150 Mz, DMS-d 6 ): δ 169.0, 167.6, 165.6, 158.0, 156.8, 155.7, 78.0, 58.2, 56.1, 52.7, 49.5, 49.2, 45.7, 41.7, 32.8, 28.1, 24.9, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: S12
13 Me Boc 12d [5-(1-{'-[2-(5-{1-['-(2-(tert- Butoxycarbonylamino)acetyl)hydrazino]-1-methylethyl}-tetrazol-1- yl)acetyl]hydrazino}-cyclopentyl)-tetrazol-1-yl]acetic acid methyl ester (12d): Prepared following the general procedure using hydrazide 11 (0.30 mmol, g), cyclopentanone (7f, 0.30 mmol, g), trimethylsilyl azide (8, 0.30 mmol, g), methyl isocyanoacetate (9, 0.30 mmol, ml) and ZnCl 2 (0.030 mmol, g). Purification by column chromatography (C 2 Cl 2 4% Me/C 2 Cl 2 ) furnished product 12d in 45% yield (0.079 g, 0.14 mmol) as a yellow solid. Mp C; R f (C 2 Cl 2 /Me 10%) MR (600 Mz, CDCl 3 ) δ 8.44 (d, J = 7.0 z, 1), 8.39 (br s, 1), 5.47 (s, 2), 5.41 (s, 2), 5.27 (br s, 1), 5.14 (br s, 1), 4.75 (br s, 1), 3.86 (s, 3), 3.77 (d, J = 5.9 z, 1), (m, 1), (m, 1), (m, 2), (m, 2), 1.59 (s, 6), 1.43 (s, 9). 13 C MR (150 Mz, CDCl 3 ): δ 169.9, 168.1, 165.6, 158.2, 157.9, 156.0, 80.3, 67.6, 57.5, 53.7, 49.9, 49.4, 42.9, 35.2, 29.7, 28.3, 25.2, 23.8, RMS (ESI) m/z: calcd. for [M+a] + C a: ; found: S13
14 ormalized Intensity Spectra of compounds 1.0 Angelica_T esp Me 10a C Figure S1: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10a. S14
15 ormalized Intensity Angelica_T esp Me 10a C Figure S2: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10a. S15
16 Me 10a C 3 Calc. [M+a] + : Figure S3: ESI-RMS of compound 10a. S16
17 ormalized Intensity Angelica_T esp Me 10b C Figure S4: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10b. S17
18 ormalized Intensity Angelica_T esp Me 10b C Figure S5: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10b. S18
19 Me 10b C 3 Calc. [M+a] + : Figure S6: ESI-RMS of compound 10b. S19
20 ormalized Intensity 1.0 Angelica_T esp Me 10c C Figure S7: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10c. S20
21 ormalized Intensity Angelica_T esp Me 10c C Figure S8: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10c. S21
22 Me 10c C 3 Calc. [M+a] + : Figure S9: ESI-RMS of compound 10c. S22
23 ormalized Intensity 1.0 Angelica_T esp Me 10d C Figure S10: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10d. S23
24 ormalized Intensity Angelica_T esp Me 10d C Figure S11: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10d. S24
25 Me C 3 10d Calc. [M+a] + : Figure S12: ESI-RMS of compound 10d. S25
26 ormalized Intensity Angelica_T esp Me C e Figure S13: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10e. S26
27 ormalized Intensity Angelica_T esp Me 10e C Figure S14: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10e. S27
28 Me C 3 10e Calc. [M+a] + : Figure S15: ESI-RMS of compound 10e. S28
29 ormalized Intensity Angelica_T esp Me 10f C Figure S16: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10f. S29
30 ormalized Intensity Angelica_T esp Me C f Figure S17: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10f. S30
31 Me 10f C 3 Calc. [M+a] + : Figure S18: ESI-RMS of compound 10f. S31
32 ormalized Intensity Angelica_T esp Me 10g C Figure S19: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10g. S32
33 ormalized Intensity Angelica_T esp Me 10g C Figure S20: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10g. S33
34 Me 10g C 3 Calc. [M+a] + : Figure S21: ESI-RMS of compound 10g. S34
35 ormalized Intensity 1.0 Angelica_T esp Me C h Figure S22: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10h. S35
36 ormalized Intensity Angelica_T esp Me 10h C Figure S23: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10h. S36
37 Me C 3 10h Calc. [M+a] + : Figure S24: ESI-RMS of compound 10h. S37
38 ormalized Intensity Angelica_T esp Me 10i Cbz Figure S25: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10i. S38
39 ormalized Intensity Angelica_T esp Me 10i Cbz Figure S26: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10i. S39
40 Me 10i Calc. [M+a] + : Cbz Figure S27: ESI-RMS of compound 10i. S40
41 ormalized Intensity 0.8 Angelica_T esp Me 10j Boc Figure S28: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10j. S41
42 ormalized Intensity Angelica_T esp Me 10j Boc Figure S29: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10j. S42
43 Me 10j Calc. [M+a] + : Boc Figure S30: ESI-RMS of compound 10j. S43
44 ormalized Intensity Angelica_T esp Me 10k Cbz Figure S31: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10k. S44
45 ormalized Intensity Angelica_T esp Me 10k Cbz Figure S32: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10k. S45
46 Me 10k Cbz Calc. [M+a] + : Figure S33: ESI-RMS of compound 10k. S46
47 ormalized Intensity Angelica_T esp Me 10l Boc Figure S34: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10l. S47
48 ormalized Intensity Angelica_T esp 0.20 Me 10l Boc Figure S35: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10l. S48
49 Me 10l Boc Calc. [M+a] + : Figure S36: ESI-RMS of compound 10l. S49
50 ormalized Intensity Angelica_T esp Me 10m Boc Figure S37: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 10m. S50
51 ormalized Intensity Angelica_T esp Me 10m Boc Figure S38: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 10m. S51
52 Figure S39: ESI-RMS of compound 10m. S52
53 ormalized Intensity 1.0 Angelica_T-38.1-hidrazida.001.esp Figure S40: 1 MR (600 Mz, DMS-d 6 ) spectrum of compound 11. S53
54 ormalized Intensity 1.0 Angelica_T-38.1-hidrazida.013.esp Boc Figure S41: 13 C MR (150 Mz, DMS-d 6 ) spectrum of compound 11. S54
55 ormalized Intensity Angelica_T-53-2-Ugi.001.esp Me 12a Boc Figure S42: 1 MR (600 Mz, DMS-d 6 ) spectrum of compound 12a. S55
56 ormalized Intensity Angelica_T-53-2-Ugi.013.esp Me 12a Boc Figure S43: 13 C MR (150 Mz, DMS-d 6 ) spectrum of compound 12a. S56
57 Figure S44: ESI-RMS of compound 12a. S57
58 ormalized Intensity 0.55 Angelica-T-41-2-Ugi.001.esp Me 12b Boc Figure S45: 1 MR (600 Mz, DMS-d 6 ) spectrum of compound 12b. S58
59 ormalized Intensity Angelica_T-41-2-Ugi.013.esp 0.15 Me 12b Boc Figure S46: 13 C MR (150 Mz, DMS-d 6 ) spectrum of compound 12b. S59
60 Me 12b Boc Calc. [M+a] + : Figure S47: ESI-RMS of compound 12b. S60
61 ormalized Intensity Angelica-T-44-2=Ugi.001.esp Me 12c Boc Figure S48: 1 MR (600 Mz, DMS-d 6 ) spectrum of compound 12c. S61
62 ormalized Intensity Angelica-T-44-2=Ugi.013.esp Me 12c Boc Figure S49: 13 C MR (150 Mz, DMS-d 6 ) spectrum of compound 12c. S62
63 Me 12c Boc Calc. [M+a] + : Figure S50: ESI-RMS of compound 12c. S63
64 ormalized Intensity 1.0 Angelica_T-45-2Uhi esp Me 12d Boc Figure S51: 1 MR (600 Mz, CDCl 3 ) spectrum of compound 12d. S64
65 ormalized Intensity Angelica_T-45-2Ugi.013.esp Me 12d Boc Figure S52: 13 C MR (150 Mz, CDCl 3 ) spectrum of compound 12d. S65
66 Me 12d Boc Calc. [M+a] + : Figure S53: ESI-RMS of compound 12d. S66
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