S1

Supporting Information

Synthesis of dihydroindeno[1,2-c]isochromene via cascade cyclization and

Friedel-Crafts reaction

Anil Kumar Saikia,* Priya Ghosh, Manash J. Deka, and Madhurjya Borah

Department of Chemistry, Indian Institute of Technology Guwahati, Assam-781039, India

Contents:

1. 1H and 13C NMR spectra of 3a-3p, 3r and 19F NMR of 3g, 3j S2-S20

2. X-crystallographic data of compound 3b S21-S22

3. HRMS Spectra of compounds 3a-3p, 3r S23-S31

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2016

S2

1H NMR and 13C NMR spectra of compound 3a

O

S3

1H NMR and 13C NMR spectra of compound 3b

O

Cl

S4

1H NMR and 13C NMR spectra of compound 3c

O

Cl

S5

1H NMR and 13C NMR spectra of compound 3d

O

Cl

S6

1H NMR and 13C NMR spectra of compound 3e

O

Cl

Cl

S7

1H NMR and 13C NMR spectra of compound 3f

O

Br

S8

1H NMR and 13C NMR spectra of compound 3g

O

F

S9

19F NMR spectrum of compound 3g

O

F

S10

1H NMR and 13C NMR spectra of compound 3h

O

MeOOC

S11

1H NMR and 13C NMR spectra of compound 3i

O

NC

S12

1H NMR and 13C NMR spectra of compound 3j

O

F3C

S13

19F NMR spectrum of compound 3j

O

F3C

S14

1H NMR and 13C NMR spectra of compound 3k

O

NO2

S15

1H NMR and 13C NMR spectra of compound 3l

O

Me

S16

1H NMR and 13C NMR spectra of compound 3m

O

Me2N

S17

1H NMR and 13C NMR spectra of compound 3n

S18

1H NMR and 13C NMR spectra of compound 3o

S19

1H NMR and 13C NMR spectra of compound 3p

S20

1H NMR and 13C NMR spectra of compound 3r

S21

The crystal parameters of compound 3b

CCDC 1483531

Formula

Formula weight

T/K

Crystal system

Space group

a/Å

b/Å

c/Å

α/º

β/º

γ/º

V/Å3

Z

Abs. Coeff./mm-1

Abs. Correction

GOF on F2

Final R indices [I > 2σ(I)]

R indices [all data]

C22H14ClO

329.78

296(2)

Monoclinic

P21/c

17.382(19)

6.286(7)

17.040(18)

90.00

117.003(18)

90.00

1659(3)

4

0.234

multi-scan

1.016

R1 = 0.0683

wR2 = 0.1508

R1 = 0.0915

wR2 = 0.1664

S22

ORTEP diagram of compound 3b, thermal ellipsoids are drawn on 50% probability level

S23

HRMS spectrum of compound 3a

HRMS spectrum of compound 3b

S24

HRMS spectrum of compound 3c

HRMS spectrum of compound 3d

S25

HRMS spectrum of compound 3e

HRMS spectrum of compound 3f

S26

HRMS spectrum of compound 3g

HRMS spectrum of compound 3h

S27

HRMS spectrum of compound 3i

HRMS spectrum of compound 3j

S28

HRMS spectrum of compound 3k

HRMS spectrum of compound 3l

S29

HRMS spectrum of compound 3m

HRMS spectrum of compound 3n

S30

HRMS spectrum of compound 3o

HRMS spectrum of compound 3p

S31

HRMS spectrum of compound 3r