Palladium-catalyzed sonogashira-coupling conjoined C-H activation: A regioselective tandem strategy to access indolo- and pyrrolo[1,2- a ]quinolines

Article abstract of DOI:10.1021/jo302112a

An operationally simple approach for the regioselective tandem synthesis of indolo[1,2-a]quinolines 4a-v and pyrrolo[1,2-a]quinolines 5a-k from 1-(2-bromophenyl)-1H-indole/pyrrole/imidazole 1a-c, 2a,b by the palladium-catalyzed sequential C-C bond formation is described. The developed approach involves the palladium-catalyzed Sonogashira coupling followed by the intramolecular C-C bond formation via C-H activation, which leads to the formation of 6-endo-dig cyclized product. This synthetic methodology accommodates wide functional group variation on alkyne, which proves to be advantageous for the structural and biological activity assessments.

Full text of DOI:10.1021/jo302112a

Supporting Information
Palladium-Catalyzed Sonogashira-Coupling Conjoined C-H
Activation: A Regioselective Tandem Strategy to Access Indolo-, and
Pyrrolo[1,2-a]quinolines
†
†, ‡
, †
Satya Prakash Shukla, Rakesh K. Tiwari and Akhilesh K. Verma,*
†
Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of
Delhi, Delhi, 110007, India
‡
Department of Biomedical & Pharmaceutical Sciences, College of Pharmacy, University of
Rhode Island, Kingston, Rhode Island, USA
averma@acbr.du.ac.in
Contents
S. No.
Page No.
1
13
1.
2.
3.
Copies of H NMR, C NMR and HRMS of Indolo[1.2-
S 3 − S 68
a]quinolines (4a−v)
1
13
Copies of H NMR, C NMR and HRMS of Pyrrolo[1.2- S 69 − S 101
a]quinolines (5a−k)
1
13
Copies of H NMR, C NMR and HRMS of 5-nitro-1-(2-(p- S 102 − S 104
tolylethynyl)phenyl)-1H-indole (6w)
S 1

1
13
Copies of H NMR, C NMR and HRMS
S 2

(
4a)
1
(
H NMR)
S 3

(
4a)
1
3
(
C NMR)
S 4

(
4a)
(
HRMS)
S 5

(
4b)
1
(
H NMR)
S 6

(
4b)
1
3
(
C NMR)
S 7

(
4b)
(
HRMS)
S 8

(
4c)
1
(
H NMR)
S 9

(
4c)
1
3
(
C NMR)
S 10

(
4c)
(
HRMS)
S 11

(
4d)
1
(
H NMR)
S 12

(
4d)
1
3
(
C NMR)
S 13

(
4d)
(
HRMS)
S 14

Me
Ph
N
(
4e)
1
(
H NMR)
S 15

Me
Ph
N
(
4e)
1
3
(
C NMR)
S 16

Me
Ph
N
(
4e)
(
HRMS)
S 17

Me
OMe
N
(
4f)
1
(
H NMR)
S 18

Me
OMe
N
(
4f)
1
3
(
C NMR)
S 19

Me
OMe
N
(
4f)
1
(
H NMR)
S 20

(
4g)
1
(
H NMR)
S 21

(
4g)
1
3
(
C NMR)
S 22

(
4g)
(
HRMS)
S 23

(
4h)
1
(
H NMR)
S 24

(
4h)
1
3
(
C NMR)
S 25

(
4h)
(
HRMS)
S 26

(
4i)
1
(
H NMR)
S 27

(
4i)
1
3
(
C NMR)
S 28

(
4i)
(
HRMS)
S 29

(
4j)
1
(
H NMR)
S 30