Rh(iii)-Catalyzed tandem indole C4-arylamination/annulation with anthranils: Access to indoloquinolines and their application in photophysical studies

Article abstract of DOI:10.1039/c9cc08372c

An efficient Rh(iii)-catalyzed straightforward strategy was developed for the tandem C4 arylamination/annulation of indole derivatives with anthranil to provide indoloquinoline moieties. This method is simple and regioselective with a wide scope and functional group tolerance. Mechanistic studies revealed the important role of the newly installed azacycle in the conversion of O-protected aldoximes to their cyano derivatives. Studies were carried out to explore the promising photophysical properties of the obtained indoloquinoline derivatives.

Full text of DOI:10.1039/c9cc08372c

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DOI: 10.1039/C9CC08372C
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Rh(III)‐Catalyzed Tandem Indole C4‐Arylamination/Annulation
with Anthranils: Access to Indoloquinolines and its Application in
Photophysical Studies
Received 00th January 20xx,
Accepted 00th January 20xx
Aniruddha Biswas,a Satabdi Bera,a Puja Poddar,a Dibakar Dhara,a and Rajarshi Samantaa*
DOI: 10.1039/x0xx00000x
An efficient Rh(III)‐catalyzed straightforward strategy was bond formations at the C4 position were accomplished under
developed for the tandem C4 arylamination/annulation of indole transition metal catalyzed conditions.6 However, C‐X bond
derivatives with anthranil to provide indoloquinoline moieties. formation at this place is very limited in literature.7,8 In
The method is simple and regioselective with a wide scope and pioneering progress, Prabhu and You group independently
functional group tolerance. Mechanistic studies revealed the established the C4‐amidation of indole moiety under Ir(III)
important role of newly installed azacycle in the conversion of O‐ catalysis using sulfonyl azides as coupling partner (Scheme 1i).7
protected aldoximes to its cyano derivatives. Studies were carried Recently; we also developed Rh(III)‐catalyzed C4‐thiolation of
out to explore the promising photophysical properties of the indole scaffold.8
Previous work on direct C-N
bond formation at C4 of indole
Previous work on coupling
of indole with anthranil
obtained indoloquinoline derivatives.
ArO2SHN
H
4
i)
CHO
CHO
ii)
4
Rh(III)
2
ArSO2N3
Ir(III)
H
Efficient and step‐economic construction of nitrogen‐
containing polyaromatic hydrocarbons (NPAHs) are always in
demand due to its enormous application as natural products,
pharmaceuticals and organic materials.1 Arguably, site‐
selective tandem C‐H bond functionalization/annulation could
be one of the efficient, straightforward and sustainable
methods to access N‐doped PAHs.2,3 Among various NPAHs,
indole fused extended π‐conjugated systems are often present
in many bioactive and organic material compounds (Figure 1).4
However, the preparation of such scaffolds are often restricted
with substrate generality, pre‐functionalized starting materials
or harsh reaction conditions.
N
N
N
N
N
R1
O
DG
Wang &
Li groups
R1
Prabhu &
You groups
N
DG
Present work
iii)
H
Indole C4-arylamination/annulation
Direct, step-economic & cascade
Azacycle guided- oxime to cyano
Extended -conjugated scaffold
Promising photophysical properties
NOR'
N
CN
O
4
N
RhIII
N
R2
N
R2
upto 83% yield
Scheme 1 Transition metal‐catalyzed C‐N bond formation at the C4‐position of indole.
Benzo[c]isoxazole (anthranil) was considered as a bifunctional
arylaminating reagent under redox‐neutral conditions for the
direct aryl amination of sp2 and sp3 C‐H bonds9,10 and
annulation to construct N‐PAHs.11‐13 Hashmi and co‐workers
elegantly explored Au(III)‐catalyzed construction of various
structurally diverse polyazaheterocycles.11 In the relevant
advancement, Li’s group and Wang’s group independently
described
the
tandem
Rh(III)‐catalyzed
C2‐
Figure 1: Important indole fused N‐PAHs
arylamination/annulation of indoles using anthranils (Scheme
1ii).12,13 Intrigued by our previous studies on indole C4
functionalization8 and step‐economic synthesis of N‐PAHs
using anthranil14, we hypothesized that the use of proper
guiding group at indole’s C3 position and anthranil as
arylaminating agent might help to provide our desired
indoloquinoline structure. Herein, we wish to disclose an
efficient Rh(III)‐catalyzed tandem C4 arylamination/annulation
of C3‐oxime tethered indole derivatives with anthranil.
Retrosynthetically, C4‐selective direct tandem arylamination
with a proximal carbonyl group and its subsequent annulation
might provide the desired indolo[4,5‐b]quinolines. Recently,
transition metal‐catalyzed site‐selective functionalizations of
indole core especially at its C4 position become an important
challenge for synthetic chemists.5‐8 Subsequently, various C‐C
a. Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur
721302, India. E‐mail: rsamanta@chem.iitkgp.ac.in
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
We embarked on our investigation with different directing
groups at the C‐3 position of indole. Directing groups like
formyl, acetyl, pivaloyl, ester, nitrile, carboxylic acid, amide did
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not produce the annulated product under [Cp*RhCl2]2/AgNTf2
catalyzed conditions (ESI, table S1, entries 1‐6).
View Article Online
DOI: 10.1039/C9CC08372C
Table 1 Optimization of indole C4 arylamination/annulations with anthranila
OMe
NOMe
N
N
N
CN
[Cp*RhCl2
]2 cat.
O
+
AgNTf2, NaOPiv
N
N
N
N
1a
R'
2aa
3a'
3a
R'
R'
entry
1c
2
3
4
5
6
7
8
solvent
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
MeOH
dioxane
toluene
Ag salt
AgNTf2
AgNTf2
AgNTf2
AgNTf2
AgNTf2
AgNTf2
AgNTf2
AgNTf2
AgSbF6
AgPF6
AgBF4
‐
AgNTf2
AgNTf2
AgNTf2
additive (mol%)
‐
NaOAc (30)
NaOAc (50)
NaOAc (100)
yield 3a (%)b
‐
<10
31
30
‐
65
75
68
69
15
‐
NaOTFA (50)
NaOPiv.H2O (20)
NaOPiv.H2O (50)
NaOPiv.H2O (100)
NaOPiv.H2O (50)
NaOPiv.H2O (50)
NaOPiv.H2O (50)
NaOPiv.H2O (20)
NaOPiv.H2O (50)
NaOPiv.H2O (50)
NaOPiv.H2O (50)
9
10
11
12
13
14
15
‐
‐
37
22
Scheme 2 Scope with different indoles. Reaction conditions: 1 (0.2 mmol), 2aa (0.1
mmol), [Cp*RhCl2]2 (3 mol%), AgNTf2 (12 mol%), NaOPiv.H2O (50 mol%), DCE (1 ml),
115 °C, 16‐20 h. aReaction was done on 3 mmol scales of 2aa and 6 mmol of 1a with 2
mol% [Cp*RhCl2]2. [b]after the first step, product was treated with 1:1 mixture of
dioxane and 6(N) HCl. Yields were calculated with respect to anthranil.
aReaction conditions: 1a (0.2 mmol), 2aa (0.1 mmol), [Cp*RhCl2]2 (3 mol%),
AgNTf2 (12 mol%), carboxylate salt (50 mol%), solvent (0.1 M), 16‐24 h, 80 °C.
bIsolated yields were calculated with respect to anthranil. Ccompound 3a’ isolated
in 10% yield
Electronically different functional groups at the C2 position of
indole moiety produced the respective products with good to
excellent yields (Scheme 2, 3g‐3i). Further, C6‐halogen ‐
substituted indole also accomplished the desired product
(Scheme 2, 3j). Next, the products with electron‐donating
substituents at the C7 position and more π‐conjugation were
Intrigued by our previous works,8,6e acetyl‐oxime and aldoxime
were also screened (ESI, table S1, entries 7‐8). Notably,
aldoxime directing group provided annulated compound 3a’ in
10% isolated yield (ESI, table S1, entry 7). However, keto‐
oxime and other related directing groups did not provide any
desired annulated product. Other relevant transition metal
catalysts like [Cp*IrCl2]2, [Cp*Co(CO)I2] and [Ru(p‐cymene)Cl2]2
did not provide desired annulated product (see ESI, table S2,
entries 1‐3). Next, in the presence of NaOAc (30 mol%) as an
additive, product 3a was obtained in very poor yield. (Table 1,
entry 2). Other similar additives like Zn(OAc)2, CsOAc,
achieved smoothly under optimized conditions (3k
C7 halogenated substrates also survived during reaction
(Scheme 2, 3p 3q). Gratifyingly, the azaindole derivative also
‐3o). Gladly,
‐
underwent the site‐selective annulation albeit in poor yield
(Scheme 2, 3r). Significantly, more complex bis‐indole di‐
aldoxime derivatives provided only mono annulated products
under the optimized conditions. Subsequent oxime removal
generated the corresponding products in synthetically
Cu(OAc)2, or LiOAc.H2O (see ESI, table S2) did not furnish 3a
.
Further, yield of 3a was marginally increased to ~30% via the
addition of higher mol% NaOAc (Table 1, entries 3‐4). Furher,
bulkier NaOPiv (20 mol%) provided improved yield of 3a to
65% (table 1, entry 6). Further tuning of the NaOPiv to 50
mol% provided the best yield of 3a to 75% (table 1, entry 7).
For more improvement, different silver salts were checked
without much success (Table 1, entries 9‐11). Other tested
common solvents were not much useful. (Table 1, entries 13‐
15).
With the optimized conditions, a thorough substrate scope for
C4, C5‐annulated indoloquinolines were explored. Different
alkyl and aryl substitution on the indole nitrogen center
provided the desired products effortlessly with moderate to
acceptable yields (Scheme 2, 3s‐3t). To check the scalability,
the reaction was carried out at 3 mmol scale of 2aa and 6
mmol of 1a with 65% isolated yield product 3a. Finally, the
structure of 3a was unequivocally confirmed by single‐crystal
x‐ray analysis (ESI, table S4, CCDC1944062). Next, anthranils
with electron‐donating groups and phenyl group afforded the
desired products in good to excellent yields (Scheme 3, 4a
To ensure the halogen compatibility, several halogen‐
substituted anthranils were tested successfully (Scheme 3, 4f
4h 4j 4k). Further, anthranil with electron‐withdrawing ester
functionality was also explored (Scheme 3, 4i).
‐4e).
‐
,
‐
To demonstrate the practical applicability, compound 3a was
debenzylated to provide the compound 3f in 72% yield
(Scheme 4i).8 Moreover, decyanation of 3a was accomplished
excellent yields (Scheme 2, 3a‐3e). Strikingly, N‐H free indole
3‐aldoxime also provided the desired annulated product
(Scheme 2, 3f) in moderate yield.
under Ni(II)‐catalyzed conditions to provide compound
5
(Scheme 4ii).15
2 | J. Name., 2012, 00, 1‐3
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DOI: 10.1039/C9CC08372C
Scheme 4 Product modifications and kinetic studies
Scheme 3 Scope with different anthranils. 1a (0.2 mmol), 2 (0.1 mmol), [Cp*RhCl2]2 (3
mol%), AgNTf2 (12 mol%), NaOPiv.H2O (50 mol%), DCE (1 ml), 115 °C, 16‐20 h. areaction
temperature 130 °C, Yields were calculated with respected to anthranil.
To realize the plausible mechanism, several control
experiments were executed. H/D scrambling at the C4 position
of 1a was observed under standard conditions in absence of
2aa (Scheme 4iii). This result indicated that indole C4−H bond
Scheme 5 Mechanistic studies.
metalation is reversible in the absence of coupling partner 2aa
.
However, in the presence of 2aa, no deuteration was
identified in the re‐isolated 1a, indicating that the following
steps of C‐H metalation were much faster (Scheme 4iv).
Incidentally, there was no H/D scrambling observed at the C2
position under the optimized conditions. In a competition
between methoxy and carboxylate attached anthranil, the
coupling favored the electron‐rich anthranil in a ~2.75:1 ratio
(Scheme 4v). Further, 3‐cyano indole derivative was explored
under optimized conditions with coupling partner 2aa.
Additionally, 1a also did not transform into its 3‐cyano indole
derivative under optimized conditions. These results indicated
that neither the first step was cyano group conversion nor the
cyano group was directing the C4‐H metalation (Scheme 5i &
ii).16 In general, the reaction was not having any significant
influence of oxygen (Scheme 5iii). Furthermore, oxime
Scheme 6 Plausible mechanism.
Intramolecular cyclization of
D affords compound 3a’. Further,
coordination of oxime and quinoline nitrogen center with
Rh(III)‐active catalyst followed by proton abstraction furnishes
the compound 3a. Importantly, some of these proposed
intermediates were also realized by LCMS analysis (see ESI).
Next, we investigated the photophysical properties of these
indoloquinolines (Figure 2). An intense absorption band below
325 nm corresponding to * transition and a comparatively
weak absorption band above 325 nm correspond to n*
transition were observed. The values of λmax and molar
attached indoloquinoline substrate
(3a’) was prepared
separately and subjected to various control experiments
(Scheme 5, table 2) to realize the cyano group formation. The
outcome revealed that newly installed quinoline ring nitrogen
center was essential to convert the oxime group into cyano
functionality under [Cp*RhCl2]2/NaOPiv based catalytic system
(Scheme 5, table 2, entry c). Based on the above experiments
and previous literature5,12‐14, a plausible mechanistic pathway
is proposed (Scheme 6). Initially, a cationic Rh(III)‐species
forms via ligand exchange. Next, Rh(III)‐species furnishes a six‐
absorption coefficients,
 (at the λmax) for the absorption band
of lower energy were calculated (ESI, Table S5). Although the
nature of the UV‐vis spectra for all the compounds was similar,
the presence of different substituents in the base structure
influenced the spectra (Figures S1‐S7). Along with UV active
properties, the indoloquinoline derivatives were also found to
be fluorescent. As representative example, the fluorescence
excitation and emission spectra of compound 3r is shown in
Figure 2. The compound is highly fluorescent, with quantum
membered rhodacycle
pivalate assisted C4‐H metalation.6b Next, the nitrogen center
of anthranil (2aa) coordinates with to generate intermediate
. Then migratory insertion of coordinated 2aa into the Rh‐C
bond affords the intermediate C, which further provides
intermediate via protodemetalation with regeneration of
A, presumably via oxime guided,
A
B
D
active Rh(III) catalyst.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1‐3 | 3
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(a) J. A. Leitch, Y. Bhonoah and C. G. Frost, ACS Catalysis.
DOI: 10.1039/C9CC08372C
L. T. Pilarski, Chem. Commun. 2017, 53, 12197.
5
6
yield value of 0.75. It is observed that the fluorescence
excitation spectrum matches exactly with the corresponding
absorption spectrum confirming the purity of the compound
(Figure 2). The obtained fluorescence spectra and the quantum
yield values (ESI, Figures S1‐S7 and Table S5) implied that the
several of these compounds might be employed as emitting
materials in OLED devices and as biosensor.
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In conclusion, we have developed a cascade Rh(III)‐catalyzed
C4‐arylamination/annulation of indole derivatives to afford
indoloquinoline derivatives using anthranil as coupling partner.
The method is straightforward with a wide scope. Mechanistic
studies determined the important role of newly installed
azacycle in the formation of cyano functionality. Studies were
carried out to explore the promising photophysical properties
of the obtained indoloquinoline derivatives.
6
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Financial support by the SERB, India (CRG/2018/000630) and
DST, India (SR/FST/CSII‐026/2013; for 500 MHz NMR) is
gratefully acknowledged. AB, SB and PP thank CSIR and IIT
Kharagpur for their fellowships.
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Conflicts of interest
There are no conflicts to declare.
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An efficient Rh(III)-catalyzed straightforward strategy was developed for the site-seleDctOiIv: e10.t1a03n9d/Ce9mCC08372C
C4 arylamination/annulation of indole derivatives with anthranil to provide indoloquinoline
moieties.

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