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1 Supporting Information for Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- and diastereoselective domino Knoevenagel [1,5]-hydride shift cyclization reaction László Tóth 1,2, Yan Fu 3, Hai Yan Zhang 3, Attila Mándi 2, Katalin E. Kövér 4, Tünde-Zita Illyés 2, Attila Kiss-Szikszai 2, Balázs Balogh 1, Tibor Kurtán 2,5, Sándor Antus *2, and Péter Mátyus *1 Address: 1 Department of Organic Chemistry, Semmelweis University, Hőgyes u. 7., 1092 Budapest, Hungary, Fax: , 2 Department of Organic Chemistry, University of Debrecen, Debrecen, P. O. Box 20, 4010 Debrecen, Hungary, 3 CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhang Jiang Hi-Tech Park, Shanghai , PR China, 4 Department of Inorganic and Analytical Chemistry, University of Debrecen, H-4010 Debrecen, Hungary and 5 Porfirin Ltd., Mikszáth K. u. 7. III/3, 4032 Debrecen, Hungary Sándor Antus - antus.sandor@science.unideb.hu; Péter Mátyus - peter.matyus@szerves.sote.hu *Corresponding author Spectroscopic data and details of calculations S1
2 Table of Contents Figure S1. Computed structures and population of low-energy conformers of trans-(2s,15as)-7b... 3 Figure S2 Computed structures and population of low-energy conformers of cis-(2r,15as)-7b... S3 Table S1 Cartesian coordinates of the low-energy DFT-optimized MMFF conformers of trans- (2S,15aS)-7d, model compound of 7a... S4 Table S2 Cartesian coordinates of the low-energy DFT-optimized MMFF conformers of trans- (2S,15aS)-7b... S5 Table S3 Cartesian coordinates of the low-energy DFT-optimized MMFF conformers of cis- (2R,15aS)-7d... S7 Table S4 Cartesian coordinates of the low-energy DFT-optimized MMFF conformers of cis- (2R,15aS)-7b... S8 Figure S3. 1 H-NMR spectra of (rac) S10 Figure S4. 13 C-NMR spectra of (rac) S11 Figure S5. IR spectra of (rac)-9 recorded as KBr disc.... S12 Figure S6. 1 H-NMR spectra of (rac) S13 Figure S7. 13 C-NMR spectra of (rac) S14 Figure S8. IR spectra of (rac)-10 recorded as KBr disc.... S15 Figure S9. 1 H-NMR spectra of (rac) S16 Figure S C-NMR spectra of (rac) S17 Figure S11. IR spectra of (rac)-5 recorded as KBr disc.... S18 Figure S12. 1 H-NMR spectra of (rac)-7a..... S19 Figure S C-NMR spectra of (rac)-7a.... S20 Figure S14. IR spectra of (rac)-7a recorded as KBr disc... S21 Figure S15. 1 H-NMR spectra of (rac)-7b.... S22 Figure S C-NMR spectra of (rac)-7b..... S23 Figure S17. IR spectra of (rac)-7b recorded as KBr disc.... S24 Figure S18. 1 H-NMR spectra of (rac)-7c.... S25 Figure S C-NMR spectra of (rac)-7c.... S26 Figure S20. IR spectra of (rac)-7c recorded as KBr disc.... S27 S2
3 Figures Figure S1. Low-energy conformers (> 1%) of trans-(2s,15as)-7b optimized at B3LYP/6-31G(d) in vacuo. Boltzmann-weights for the same conformers in the B3LYP/TZVP PCM/CHCl 3 calculations are 95.8% and 3.6%, respectively. Figure S2. Low-energy conformers (> 1%) of cis-(2r,15as)-7b optimized at B3LYP/6-31G(d) in vacuo. Boltzmann-weights for the same conformers in the B3LYP/TZVP PCM/CHCl 3 calculations are 82.5% and 14.1%, respectively. S3
4 Tables Table S1. Cartesian coordinates of the low-energy DFT-optimized MMFF conformers of trans- (2S,15aS)-7d, model compound of 7a, calculated at B3LYP/6-31G(d) level of theory in vacuo. Conformer A Standard Orientation (Ångstroms) I Atom X Y Z 1 C C C C H H H H C C O C C H H C N N C C C N C O O O C C C C C C H H H C C C C C C H H H H H H H H H C H H N O O B3LYP Energy = a.u.; E+ZPVE = a.u. S4
5 Table S2. Cartesian coordinates of the low-energy DFT-optimized MMFF conformers of trans- (2S,15aS)-7b calculated at B3LYP/6-31G(d) level of theory in vacuo. Conformer A Standard Orientation (Ångstroms) I Atom X Y Z 1 C C C C H H H H C C O C C H H C N O C C C O C O O C C C C C C C H H H C C C C C C H H H H H H H C H H H H H H C H H N O O B3LYP Energy = a.u.; E+ZPVE = a.u. S5
6 Conformer B Standard Orientation (Ångstroms) I Atom X Y Z 1 C C C C H H H H C C O C C H H C N O C C C O C O O C C C C C C C H H H C C C C C C H H H H H H H C H H H H H H C H H N O O B3LYP Energy = a.u.; E+ZPVE = a.u. S6
7 Table S3. Cartesian coordinates of the low-energy DFT-optimized MMFF conformers of cis- (2R,15aS)-7d, model compound of 7a, calculated at B3LYP/6-31G(d) level of theory in vacuo. Conformer A Standard Orientation (Ångstroms) I Atom X Y Z 1 C C C C H H H H C C O C C H H C N N C C C N C O O O C C C C C C H H H C C C C C C H H H H H H H H H C H H N O O B3LYP Energy = a.u.; E+ZPVE = a.u. S7
8 Table S4. Cartesian coordinates of the low-energy DFT-optimized MMFF conformers of cis- (2R,15aS)-7b calculated at B3LYP/6-31G(d) level of theory in vacuo. Conformer A Standard Orientation (Ångstroms) I Atom X Y Z 1 C C C C H H H H C C O C C H H C N O C C C O C O O C C C C C C C H H H C C C C C C H H H H H H H C H H H H H H C H H N O O B3LYP Energy = a.u.; E+ZPVE = a.u. S8
9 Conformer B Standard Orientation (Ångstroms) I Atom X Y Z 1 C C C C H H H H C C O C C H H C N O C C C O C O O C C C C C C C H H H C C C C C C H H H H H H H C H H H H H H C H H N O O B3LYP Energy = a.u.; E+ZPVE = a.u. S9
10 Ph a,b NH Figure S3. 1 H-NMR spectra of (rac)-9 measured in CDCl 3 (400 MHz). S10
11 3,5 2, a 1 5a 3 Figure S4. 13 C-NMR spectra of (rac)-9 measured in CDCl 3 (100 MHz). S11
12 Figure S5. IR spectra of (rac)-9 recorded as KBr disc. S12
13 Ph 6,9 5 7,8 2 3-H eq 3-H ax Figure S6. 1 H-NMR spectra of (rac)-10 measured in CDCl 3 (400 MHz). S13
14 3,5 6, 4 2, a 1 5a 3 5 Figure S7. 13 C-NMR spectra of (rac)-10 measured in CDCl 3 (100 MHz). S14
15 Figure S8. IR spectra of (rac)-10 recorded as KBr disc. S15
16 CHO Ph 3 5 6,7 6 9, a,b 3-H eq 3-H ax Figure S9. 1 H-NMR spectra of (rac)-5 measured in CDCl 3 (400 MHz). S16
17 3,5 2,6 5, 4, 6 7 8, CHO 1 9a a 3 5 Figure S C-NMR spectra of (rac)-5 measured in CDCl 3 (100 MHz). S17
18 Figure S11. IR spectra of (rac)-5 recorded as KBr disc. S18
19 Me Me 18, Ph 16, Ph 15a b 3b 3a 9a Figure S12. 1 H-NMR spectra of (rac)-7a measured in CDCl 3 (400 MHz). S19
20 3, 5 2, a 2 x Me a 19a a 15b Figure S C-NMR spectra of (rac)-7a measured in CDCl 3 (100 MHz). S20
21 Figure S14. IR spectra of (rac)-7a recorded as KBr disc. S21
22 Me Me Ph , a-H eq 3ax 9 9 Figure S15. 1 H-NMR spectra of (rac)-7b measured in CDCl 3 (400 MHz). S22
23 3, 5 2, a 13-Me 13-Me a 19a b Figure S C-NMR spectra of (rac)-7b measured in CDCl 3 (100 MHz). S23
24 Figure S17. IR spectra of (rac)-7b recorded as KBr disc. S24
25 Ph 12, 13, Figure S18. 1 H-NMR spectra of (rac)-7c measured in CDCl MHz. S25
26 3, 5, 14 2, 6, a a 10 CN CN Figure S C-NMR spectra of (rac)-7c measured in CDCl MHz. S26
27 Figure S20. IR spectra of (rac)-7c recorded as KBr disc. S27
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