Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis...
Transcript of Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis...
![Page 1: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/1.jpg)
S1
Supporting Information
Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-
b]pyrrole-4(1H)-ones and Their Conversion to Coumarin Bearing
Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via Oxidative
Cleavage Reaction
Abdolali Alizadeh*,a Rashid Ghanbaripoura Masoumeh Feizabadia Long-Guan Zhub and Michal Dusekc
aDepartment of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, IranbDepartment of Chemistry, Zhejiang University, Hangzhou 310027, PR China
cInstitute of Physics ASCR, Na Slovance 2, 182 21 Prague, Czech Republic
The Table of Contents
Title, author’s name, address and table of contents S11H and 13C NMR spectrums of 3a-g S2-S221H and 13C NMR spectrums of 4a and 5a S23-S281H and 13C NMR spectrums of 7a-c and 7f S29-S36
Ortep diagram of 3a S37
Ortep diagram of 7a S38
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2015
![Page 2: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/2.jpg)
S2
1H NMR of 3a
O
O
N
O
OH
HO
O
![Page 3: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/3.jpg)
S3
1H NMR of 3a (expand)
O
O
N
O
OH
HO
O
![Page 4: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/4.jpg)
S4
13C NMR of 3a
O
O
N
O
OH
HO
O
![Page 5: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/5.jpg)
S5
1H NMR of 3b
O
O
N
O
OH
HO
O
Cl
![Page 6: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/6.jpg)
S6
1H NMR of 3b (expand)
O
O
N
O
OH
HO
O
Cl
![Page 7: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/7.jpg)
S7
13C NMR of 3b
O
O
N
O
OH
HO
O
Cl
![Page 8: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/8.jpg)
S8
1H NMR of 3c
O
O
N
O
OH
HO
O
CH3
![Page 9: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/9.jpg)
S9
1H NMR of 3c (expand)
O
O
N
O
OH
HO
O
CH3
![Page 10: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/10.jpg)
S10
13C NMR of 3c
O
O
N
O
OH
HO
O
CH3
![Page 11: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/11.jpg)
S11
1H NMR of 3d
O
O
N
O
OH
HO
O
CH3O
![Page 12: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/12.jpg)
S12
1H NMR of 3d (expand)
O
O
N
O
OH
HO
O
CH3O
![Page 13: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/13.jpg)
S13
13C NMR of 3d
O
O
N
O
OH
HO
O
CH3O
![Page 14: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/14.jpg)
S14
1H NMR of 3e
O
O
N
O
OH
HO
O
CH3O
O2N
![Page 15: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/15.jpg)
S15
1H NMR of 3e (expand)
O
O
N
O
OH
HO
O
CH3O
O2N
![Page 16: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/16.jpg)
S16
13C NMR of 3e
O
O
N
O
OH
HO
O
CH3O
O2N
![Page 17: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/17.jpg)
S17
1H NMR of 3f
O
O
N
O
OH
HO
O
OCH3
![Page 18: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/18.jpg)
S18
1H NMR of 3f (expand)
O
O
N
O
OH
HO
O
OCH3
![Page 19: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/19.jpg)
S19
13C NMR of 3f
O
O
N
O
OH
HO
O
OCH3
![Page 20: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/20.jpg)
S20
1H NMR of 3g
O
O
N
O
OH
HO
O
OCH3
Cl
![Page 21: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/21.jpg)
S21
1H NMR of 3g (expand)
O
O
N
O
OH
HO
O
OCH3
Cl
![Page 22: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/22.jpg)
S22
13C NMR of 3g
O
O
N
O
OH
HO
O
OCH3
Cl
![Page 23: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/23.jpg)
S23
1H NMR of 4a
O O
O OH
CH3
![Page 24: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/24.jpg)
S24
1H NMR of 4a (expand)
O O
O OH
CH3
![Page 25: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/25.jpg)
S25
13C NMR of 4a
O O
O OH
CH3
![Page 26: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/26.jpg)
S26
1H NMR of 5a
O O
O N
CH3
H
![Page 27: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/27.jpg)
S27
1H NMR of 5a (expand)
O O
O N
CH3
H
![Page 28: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/28.jpg)
S28
13C NMR of 5a
O O
O N
CH3
H
![Page 29: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/29.jpg)
S29
1H NMR of 7a
O
N
O O
Me
O
O
O
![Page 30: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/30.jpg)
S30
13C NMR of 7a
O
N
O O
Me
O
O
O
![Page 31: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/31.jpg)
S31
1H NMR of 7b
O
N
O O
Me
O
O
O
Cl
![Page 32: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/32.jpg)
S32
13C NMR of 7b
O
N
O O
Me
O
O
O
Cl
![Page 33: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/33.jpg)
S33
1H NMR of 7c
O
N
O O
Me
O
O
O
Me
![Page 34: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/34.jpg)
S34
13C NMR of 7c
O
N
O O
Me
O
O
O
Me
![Page 35: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/35.jpg)
S35
1H NMR of 7f
O
N
O O
Me
O
O
O
OMe
![Page 36: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/36.jpg)
S36
13C NMR of 7f
O
N
O O
Me
O
O
O
OMe
![Page 37: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/37.jpg)
S37
ORTEP diagram for 3a
![Page 38: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/38.jpg)
S38
ORTEP diagram for 7a
![Page 39: Spiro[isobenzofuran-1,2’-pyrrole] Moiety compounds via ... · S1 Supporting Information Synthesis of 3-[(Coumarinyl)carbonyl]-3a,8b-dihyroindeno[1,2-b]pyrrole-4(1H)-ones and Their](https://reader035.fdocuments.us/reader035/viewer/2022062415/5fd25b6011962d26ac7b037e/html5/thumbnails/39.jpg)
S39