For Molecular Diversity

For Molecular Diversity

Supporting information

for

Synthesis and antifungal activity of dehydroabietic acid-based 1,3,4-thiadiazole-thiazolidinone compounds

Naiyuan Chen1·WenguiDuan[1]·Guishan Lin1·Luzhi Liu1· Ruizhang1·Dianpeng Li2

The IR, 1H NMR,13C NMR, ESI-MS datafor the synthesized compounds

Contents

1. 1H NMR spectrum of 2-Chloroacetamide-5-dehydroabietyl-1,3,4-thiadiazole (3)

2. 2-(2-imino-5-dehydroabietyl-1,3,4-thiadiazole)-1,3-thiazolidin-4-one (4)

2.1. FTIR spectrum of 2-(2-imino-5-dehydroabietyl-1,3,4-thiadiazole)-1,3-thiazolidin-4-one (4)

2.2. 1H NMR spectrum of 2-(2-imino-5-dehydroabietyl-1,3,4-thiadiazole)-1,3-thiazolidin-4-one (4)

2.3. 13C NMR spectrum of 2-(2-imino-5-dehydroabietyl-1,3,4-thiadiazole)-1,3-thiazolidin-4-one (4)

2.4. ESI-MS spectrum2-(2-imino-5-dehydroabietyl-1,3,4-thiadiazole)-1,3-thiazolidin-4-one (4)

3. Compound 5a (R=H)

3.1. FTIR spectrum of Compound 5a (R=H)

3.2. 1H NMR spectrum of Compound 5a (R=H)

3.3. 13C NMR spectrum of Compound 5a (R=H)

3.4. ESI-MS spectrumCompound 5a (R=H)

4. Compound 5b (R=o-F)

4.1. FTIR spectrum of Compound 5b (R=o-F)

4.2. 1H NMR spectrum of Compound 5b (R=o-F)

4.3. 13C NMR spectrum of Compound 5b (R=o-F)

4.4. ESI-MS spectrumCompound 5b (R=o-F)

5. Compound 5c (R=p-F)

5.1. FTIR spectrum of Compound 5c (R=p-F)

5.2. 1H NMR spectrum of Compound 5c (R=p-F)

5.3. 13C NMR spectrum of Compound 5c (R=p-F)

5.4. ESI-MS spectrumCompound 5c (R=p-F)

6. Compound 5d (R=o-Cl)

6.1. FTIR spectrum of Compound 5d (R=o-Cl)

6.2. 1H NMR spectrum of Compound 5d (R=o-Cl)

6.3. 13C NMR spectrum of Compound 5d (R=o-Cl)

6.4. ESI-MS spectrumCompound 5d (R=o-Cl)

7. Compound 5e (R=p-Cl)

7.1. FTIR spectrum of Compound 5e (R=p-Cl)

7.2. 1H NMR spectrum of Compound 5e (R=p-Cl)

7.3. 13C NMR spectrum of Compound 5e (R=p-Cl)

7.4. ESI-MS spectrumCompound 5e (R=p-Cl)

8. Compound 5f (R=o-Br)

8.1. FTIR spectrum of Compound 5f (R=o-Br)

8.2. 1H NMR spectrum of Compound 5f (R=o-Br)

8.3. 13C NMR spectrum of Compound 5f (R=o-Br)

8.4. ESI-MS spectrumCompound 5f (R=o-Br)

9. Compound 5g (R=p-Br)

9.1. FTIR spectrum of Compound 5g (R=p-Br)

9.2. 1H NMR spectrum of Compound 5g (R=p-Br)

9.3. 13C NMR spectrum of Compound 5g (R=p-Br)

9.4. ESI-MS spectrumCompound 5g (R=p-Br)

10. Compound 5h (R=o-NO2)

10.1. FTIR spectrum of Compound 5h (R=o-NO2)

10.2.1H NMR spectrum of Compound 5h (R=o-NO2)

10.3. 13C NMR spectrum of Compound 5h (R=o-NO2)

10.4. ESI-MS spectrumCompound 5h (R=o-NO2)

11. Compound 5i (R=m-NO2)

11.1. FTIR spectrum of Compound 5i (R=m-NO2)

11.2. 1H NMR spectrum of Compound 5i (R=m-NO2)

11.3. 13C NMR spectrum of Compound 5i (R=m-NO2)

11.4. ESI-MS spectrumCompound 5i (R=m-NO2)

12. Compound 5j (R=p-NO2)

12.1. FTIR spectrum of Compound 5j (R=p-NO2)

12.2. 1H NMR spectrum of Compound 5j (R=p-NO2)

12.3. 13C NMR spectrum of Compound 5j (R=p-NO2)

12.4. ESI-MS spectrumCompound 5j (R=p-NO2)

13. Compound 5k (R=o-CH3)

13.1. FTIR spectrum of Compound 5k (R=o-CH3)

13.2. 1H NMR spectrum of Compound 5k (R=o-CH3)

13.3. 13C NMR spectrum of Compound 5k (R=o-CH3)

13.4. ESI-MS spectrumCompound 5k (R=o-CH3)

14. Compound 5l (R=m-CH3)

14.1. FTIR spectrum of Compound 5l (R=m-CH3)

14.2. 1H NMR spectrum of Compound 5l (R=m-CH3)

14.3. 13C NMR spectrum of Compound 5l (R=m-CH3)

14.4. ESI-MS spectrumCompound 5l (R=m-CH3)

15. Compound 5m (R=p-CH3)

15.1. FTIR spectrum of Compound 5m (R=p-CH3)

15.2. 1H NMR spectrum of Compound 5m (R=p-CH3)

15.3. 13C NMR spectrum of Compound 5m (R=p-CH3)

15.4. ESI-MS spectrumCompound 5m (R=p-CH3)

16. Compound 5n (R=m-OCH3)

16.1. FTIR spectrum of Compound 5n (R=m-OCH3)

16.2. 1H NMR spectrum of Compound 5n (R=m-OCH3)

16.3. 13C NMR spectrum of Compound 5n (R=m-OCH3)

16.4. ESI-MS spectrumCompound 5n (R=m-OCH3)

17. Compound 5o (R=o-OCH3)

17.1. FTIR spectrum of Compound5o (R=o-OCH3)

17.2. 1H NMR spectrum of Compound 5o (R=o-OCH3)

17.3. 13C NMR spectrum of Compound 5o (R=o-OCH3)

17.4. ESI-MS spectrumCompound 5o (R=o-OCH3)

18. Compound 5p (R=p-OCH3)

18.1. FTIR spectrum of Compound 5p (R=p-OCH3)

18.2. 1H NMR spectrum of Compound 5p (R=p-OCH3)

18.3. 13C NMR spectrum of Compound 5p (R=p-OCH3)

18.4. ESI-MS spectrumCompound 5p (R=p-OCH3)

1. 1H NMR spectrum of 2-Chloroacetamide-5-dehydroabietyl-1,3,4-thiadiazole (3)

2. 2-(2-imino-5-dehydroabietyl-1,3,4-thiadiazole)-1,3-thiazolidin-4-one (4)

2.1. FTIR spectrum of 2-(2-imino-5-dehydroabietyl-1,3,4-thiadiazole)-1,3-thiazolidin-4-one (4)

2.2. 1H NMR spectrum of 2-(2-imino-5-dehydroabietyl-1,3,4-thiadiazole)-1,3-thiazolidin-4-one (4)

2.3. 13C NMR spectrum of 2-(2-imino-5-dehydroabietyl-1,3,4-thiadiazole)-1,3-thiazolidin-4-one (4)

2.4. ESI-MS spectrum2-(2-imino-5-dehydroabietyl-1,3,4-thiadiazole)-1,3-thiazolidin-4-one (4)

3. Compound 5a (R=H)

3.1. FTIR spectrum of Compound 5a (R=H)

3.2. 1H NMR spectrum of Compound 5a (R=H)

3.3. 13C NMR spectrum of Compound 5a (R=H)

3.4. ESI-MS spectrumCompound 5a (R=H)

4. Compound 5b (R=o-F)

4.1. FTIR spectrum of Compound5b (R=o-F)

4.2. 1H NMR spectrum of Compound 5b (R=o-F)

4.3. 13C NMR spectrum of Compound 5b (R=o-F)

4.4. ESI-MS spectrumCompound 5b (R=o-F)

5. Compound 5c (R=p-F)

5.1. FTIR spectrum of Compound 5c (R=p-F)

5.2. 1H NMR spectrum of Compound 5c (R=p-F)

5.3. 13C NMR spectrum of Compound 5c (R=p-F)

5.4. ESI-MS spectrumCompound 5c (R=p-F)

6. Compound 5d (R=o-Cl)

6.1. FTIR spectrum of Compound 5d (R=o-Cl)

6.2. 1H NMR spectrum of Compound 5d (R=o-Cl)

6.3. 13C NMR spectrum of Compound 5d (R=o-Cl)

6.4. ESI-MS spectrumCompound 5d (R=o-Cl)

7. Compound 5e (R=p-Cl)

7.1. FTIR spectrum of Compound 5e (R=p-Cl)

7.2. 1H NMR spectrum of Compound 5e (R=p-Cl)

7.3. 13C NMR spectrum of Compound 5e (R=p-Cl)

7.4. ESI-MS spectrumCompound 5e (R=p-Cl)

8. Compound 5f (R=o-Br)

8.1. FTIR spectrum of Compound 5f (R=o-Br)

8.2. 1H NMR spectrum of Compound 5f (R=o-Br)

8.3. 13C NMR spectrum of Compound 5f (R=o-Br)

8.4. ESI-MS spectrumCompound 5f (R=o-Br)

9. Compound 5g (R=p-Br)

9.1. FTIR spectrum of Compound 5g (R=p-Br)

9.2. 1H NMR spectrum of Compound 5g(R=p-Br)

9.3. 13C NMR spectrum of Compound 5g (R=p-Br)

9.4. ESI-MS spectrumCompound 5g (R=p-Br)

10. Compound 5h (R=o-NO2)

10.1. FTIR spectrum of Compound 5h (R=o-NO2)

10.2.1H NMR spectrum of Compound 5h (R=o-NO2)

10.3. 13C NMR spectrum of Compound 5h (R=o-NO2)

10.4. ESI-MS spectrumCompound 5h (R=o-NO2)

11. Compound 5i (R=m-NO2)

11.1. FTIR spectrum of Compound 5i (R=m-NO2)

11.2. 1H NMR spectrum of Compound 5i (R=m-NO2)

11.3. 13C NMR spectrum of Compound 5i (R=m-NO2)

11.4. ESI-MS spectrumCompound 5i (R=m-NO2)

12. Compound 5j (R=p-NO2)

12.1. FTIR spectrum of Compound 5j (R=p-NO2)

12.2. 1H NMR spectrum of Compound 5j (R=p-NO2)

12.3. 13C NMR spectrum of Compound 5j (R=p-NO2)

12.4. ESI-MS spectrumCompound 5j (R=p-NO2)

13. Compound 5k (R=o-CH3)

13.1. FTIR spectrum of Compound 5k (R=o-CH3)

13.2. 1H NMR spectrum of Compound 5k (R=o-CH3)

13.3. 13C NMR spectrum of Compound 5k (R=o-CH3)

13.4. ESI-MS spectrumCompound 5k (R=o-CH3)

14. Compound 5l (R=m-CH3)

14.1. FTIR spectrum of Compound 5l (R=m-CH3)

14.2. 1H NMR spectrum of Compound 5l (R=m-CH3)

14.3. 13C NMR spectrum of Compound 5l (R=m-CH3)

14.4. ESI-MS spectrumCompound 5l (R=m-CH3)

15. Compound 5m (R=p-CH3)

15.1. FTIR spectrum of Compound 5m (R=p-CH3)

15.2. 1H NMR spectrum of Compound 5m (R=p-CH3)

15.3. 13C NMR spectrum of Compound 5m (R=p-CH3)

15.4. ESI-MS spectrumCompound 5m (R=p-CH3)

16. Compound 5n (R=m-OCH3)

16.1. FTIR spectrum of Compound 5n (R=m-OCH3)

16.2. 1H NMR spectrum of Compound 5n (R=m-OCH3)

16.3. 13C NMR spectrum of Compound 5n (R=m-OCH3)

16.4. ESI-MS spectrumCompound 5n (R=m-OCH3)

17. Compound 5o (R=o-OCH3)

17.1. FTIR spectrum of Compound5o (R=o-OCH3)

17.2. 1H NMR spectrum of Compound 5o (R=o-OCH3)

17.3. 13C NMR spectrum of Compound 5o (R=o-OCH3)

17.4. ESI-MS spectrumCompound 5o (R=o-OCH3)

18. Compound 5p (R=p-OCH3)

18.1. FTIR spectrum of Compound 5p (R=p-OCH3)

18.2. 1H NMR spectrum of Compound 5p (R=p-OCH3)

18.3. 13C NMR spectrum of Compound 5p (R=p-OCH3)

18.4. ESI-MS spectrumCompound 5p (R=p-OCH3)

Wengui Duan

1 School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004,Guangxi, P.R. China.

2 Guangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences, Guilin 541006, Guangxi, P.R. China.