1

Regioselective α-arylation of coumarins and 2-pyridones with phenylhydrazines under transition-metal-free condition Parul Chauhan,a Makthala Ravi,a Shikha Singh,a Prashant Prajapati,b Prem. P. Yadav*a

aDivisions of Medicinal and Process Chemistry,CSIR-Central Drug Research Institute, Lucknow- 226001, India.

bNational Institute of Pharmaceutical Education and Research, Raebareli, India-229010.

Table of Contents

1. Copies of 1H and 13C NMR spectra 2-40

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2015

2

1H NMR Spectra of (3a) (400 MHz, CDCl3)

13C NMR Spectra of (3a) (100 MHz, CDCl3)

O O

Cl

O O

Cl

3

1H NMR Spectra of (3b) (400 MHz, CDCl3)

13C NMR Spectra of (3b) (100 MHz, CDCl3)

O O

Br

O O

Br

4

1H NMR Spectra of (3c) (400 MHz, CDCl3)

13C NMR Spectra of (3c) (100 MHz, CDCl3)

O O

F

O O

F

5

1H NMR Spectra of (3d) (400 MHz, CDCl3)

13C NMR Spectra of (3d) (100 MHz, CDCl3)

O O

F

O O

F

O O

CN

6

1H NMR Spectra of (3e) (300 MHz, CDCl3)

13C NMR Spectra of (3e) (75 MHz, CDCl3)

O O

CN

O O

CN

7

1H NMR Spectra of (3f) (400 MHz, CDCl3)

13C NMR Spectra of (3f) (100 MHz, CDCl3)

O O

O O

8

1H NMR Spectra of (3g) (400 MHz, CDCl3)

13C NMR Spectra of (3g) (100 MHz, CDCl3)

O O

Me

O O

Me

9

1H NMR Spectra of (3h) (400 MHz, CDCl3)

13C NMR Spectra of (3h) (100 MHz, CDCl3)

O O

Me

Me

O O

Me

Me

10

1H NMR Spectra of (3i) (400 MHz, CDCl3)

13C NMR Spectra of (3i) (100 MHz, CDCl3)

O O

OMe

O O

OMe

11

1H NMR Spectra of (3j) (400 MHz, CDCl3)

13C NMR Spectra of (3j) (100 MHz, CDCl3)

O O

Cl

Me

O O

Cl

Me

12

1H NMR Spectra of (3k) (400 MHz, CDCl3)

13C NMR Spectra of (3k) (100 MHz, CDCl3)

O O

F

Me

O O

F

Me

13

1H NMR Spectra of (3l) (400 MHz, CDCl3)

13C NMR Spectra of (3l) (100 MHz, CDCl3)

O O

Me

O O

Me

14

1H NMR Spectra of (3m) (400 MHz, CDCl3)

13C NMR Spectra of (3m) (100 MHz, CDCl3

O O

OMe

Me

O O

OMe

Me

15

1H NMR Spectra of (3n) (400 MHz, CDCl3)

13C NMR Spectra of (3n) (100 MHz, CDCl3)

O O

Me

Me

O O

Me

Me

16

1H NMR Spectra of (3o) (400 MHz, DMSO-d6)

13C NMR Spectra of (3o) (100 MHz, DMSO-d6)

O O

Cl

HO

O O

Cl

HO

17

1H NMR Spectra of (3p) (400 MHz, DMSO-d6)

13C NMR Spectra of (3p) (100 MHz, DMSO-d6)

O O

F

HO

O O

F

HO

18

1H NMR Spectra of (3q) (400 MHz, DMSO-d6)

13C NMR Spectra of (3q) (100 MHz, DMSO-d6)

O OHO

Br

O OHO

Br

19

1H NMR Spectra of (3r) (400 MHz, DMSO-d6)

13C NMR Spectra of (3r) (100 MHz, DMSO-d6)

O OHO

O OHO

20

1H NMR Spectra of (3s) (400 MHz, DMSO-d6)

13C NMR Spectra of (3s) (100 MHz, DMSO-d6)

O O

Me

HO

O O

Me

HO

21

1H NMR Spectra of (3t) (400 MHz, DMSO-d6)

13C NMR Spectra of (3t) (100 MHz, DMSO-d6)

O O

Me

Me

HO

O O

Me

Me

HO

22

1H NMR Spectra of (3u) (400 MHz, DMSO-d6)

13C NMR Spectra of (3u) (100 MHz, DMSO-d6)

O O

OMe

HO

O O

OMe

HO

23

1H NMR Spectra of (3v) (400 MHz, CDCl3)

13C NMR Spectra of (3v) (400 MHz, CDCl3)

O O

Cl

MeO

O O

Cl

MeO

24

1H NMR Spectra of (3w) (400 MHz, CDCl3)

13C NMR Spectra of (3w) (400 MHz, CDCl3)

O O

Me

MeO

O O

Me

MeO

25

1H NMR Spectra of (3y) (400 MHz, CDCl3)

13C NMR Spectra of (3y) (400 MHz, CDCl3)

O O

Me

Cl

O O

Me

Cl

26

1H NMR Spectra of (3z) (400 MHz, CDCl3)

13C NMR Spectra of (3z) (400 MHz, CDCl3)

O O

OMe

Br

O O

OMe

Br

27

1H NMR Spectra of (3za) (400 MHz, DMSO- d6)

13C NMR Spectra of (3za) (100 MHz, DMSO- d6)

NH

O

Cl

NH

O

Cl

28

1H NMR Spectra of (3zb) (400 MHz, DMSO- d6)

13C NMR Spectra of (3zb) (100 MHz, DMSO- d6)

NH

O

Me

NH

O

Me

29

1H NMR Spectra of (4) (400 MHz, DMSO- d6)

13C NMR Spectra of (4) (400 MHz, DMSO- d6)

O O

N

Cl

HO

O O

N

Cl

HO

30

1H NMR Spectra of (6a) (400 MHz, DMSO- d6)

13C NMR Spectra of (6a) (100 MHz,DMSO- d6)

NH

O

NH

O

31

1H NMR Spectra of (6b) (400 MHz, DMSO- d6)

13C NMR Spectra of (6b) (100 MHz,DMSO- d6)

NH

O

Cl

NH

O

Cl

32

1H NMR Spectra of (6c) (400 MHz, DMSO- d6)

13C NMR Spectra of (6c) (100 MHz,DMSO- d6)

NH

O

Br

NH

O

Br

33

1H NMR Spectra of (6d) (400 MHz, DMSO- d6)

13C NMR Spectra of (6d) (100 MHz,DMSO- d6)

NH

O

F

NH

O

F

34

1H NMR Spectra of (6e) (400 MHz, DMSO- d6)

13C NMR Spectra of (6e) (100 MHz,DMSO- d6)

NH

O

Me

NH

O

Me

35

1H NMR Spectra of (6f) (400 MHz, CDCl3)

13C NMR Spectra of (6f) (100 MHz,CDCl3)

N O

CH3

N O

CH3

36

1H NMR Spectra of (6g) (400 MHz, CDCl3)

13C NMR Spectra of (6g) (100 MHz,CDCl3)

N O

Cl

CH3

N O

Cl

CH3

37

1H NMR Spectra of (6h) (400 MHz, CDCl3)

13C NMR Spectra of (6h) (100 MHz,CDCl3)

N O

Br

CH3

N O

Br

CH3

38

1H NMR Spectra of (6i) (400 MHz, DMSO- d6)

13C NMR Spectra of (6i) (100 MHz,DMSO- d6)

N O

Me

CH3

N O

Me

CH3

39

1H NMR Spectra of (6j) (400 MHz, CDCl3)

13C NMR Spectra of (6j) (100 MHz,CDCl3)

N O

OMe

CH3

N O

OMe

CH3

40

1H NMR Spectra of (7) (400 MHz, CDCl3)

13C NMR Spectra of (7) (100 MHz,CDCl3)

NC

ON

NC

ON