Synthesis of Fused B-Containing Heterocyclic Compounds and Their Relevant Optical Properties

Article abstract of DOI:10.1002/ejoc.201701790

A series of fused 4,5-borazaropyrrolo[1,2-a]quinolines have been prepared from potassium organotrifluoroborates and substituted 1-(2-aminophenyl)pyrroles via direct formation of C–B and N–B bonds. The target products were obtained in moderate to high yields under mild conditions. The optical properties of some products were investigated by UV/Vis spectroscopy and spectrofluorometry. Moreover, the influence of structural modification on the spectroscopic and electronic properties was studied by DFT calculations.

Full text of DOI:10.1002/ejoc.201701790

A Journal of
Accepted Article
Title: Synthesis of Fused B-containing Heterocyclic Compounds and
Studied their Relevent Optical Properties
Authors: zhenyu an, mingzhong wu, jie kang, jixiang ni, zhenjie qi,
bingxiang yuan, and Long Yan
This manuscript has been accepted after peer review and appears as an
Accepted Article online prior to editing, proofing, and formal publication
of the final Version of Record (VoR). This work is currently citable by
using the Digital Object Identifier (DOI) given below. The VoR will be
published online in Early View as soon as possible and may be different
to this Accepted Article as a result of editing. Readers should obtain
the VoR from the journal website shown below when it is published
to ensure accuracy of information. The authors are responsible for the
content of this Accepted Article.
To be cited as: Eur. J. Org. Chem. 10.1002/ejoc.201701790
Link to VoR: http://dx.doi.org/10.1002/ejoc.201701790
Supported by

10.1002/ejoc.201701790
European Journal of Organic Chemistry
COMMUNICATION
Synthesis of Fused B-containing Heterocyclic Compounds and
Studied their Relevent Optical Properties
Zhenyu An, Mingzhong Wu, Jie Kang, Jixiang Ni, Zhenjie Qi, Bingxiang Yuan and Rulong Yan*
Abstract: A series of fused 4,5-borazaropyrrolo[1,2-a]quinolines
have been prepared from potassium organotrifluoroborates and
substituted 1-(2-aminophenyl)pyrroles via C-B and N-B bonds
formation directly. Target products were obtained in moderate to
high yields under mild condition. Optical properties of some products
were investigated by UV/Vis spectroscopy and spectrofluorometry.
Moreover, the influence of structural modification on the
spectroscopic and electronic properties was studied by DFT
calculation.
Azaborines, as B-containing N-heterocyclic compounds,[1] have
attracted much attentions in material science and medicinal
chemistry.[2] Furthermore, azaborines with B-N unit as valuable
building blocks exhibit a novel behavior in material science and
biomedical research field,[3] such as fluorescent dyes[4] and
biological labeling.[5] Moreover, the B-N unit has a strong dipole
moment, and replacing C=C with B-N unit decreases the
HOMO-LUMO gap, which often results in chemiluminescent
materials.[6] So the photophysical properties of B-N containing
heterocyclic compounds are distinctly different from those
corresponding all-carbon aromatic systems. Parvez reported
Scheme 1. Synthesis of B-substituted azaborines.
that phenanthrene analogues with B-N moieties could afford
With high interest in construction of azaborines, 1-(2-amino
blue light emission with good quantum efficiencies.[7]
phenyl)pyrrole 1a and potassium phenyltrifluoroborate 2a were
In past several decades, the synthesis of B-N containing
chosen as model substrates for our studies. In the presence of
heterocyclic compounds had become a popular strategy to
SiCl4, Et3N, and 1:1 mixture of PhMe/CH3CN at ambient
increase structural diversity and provided new isosteric aromatic
temperature, the desired product 3aa was generated in 65%
systems. Many procedures for azaborines construction have
yield (Table 1, entry 1). Next, when the temperature was
been
reported.[8]
In
1959,
the
first
example
of
o
improved to 80 C and the quantity of the Et3N was improved to
borazaronaphthalene was prepared by Dewar.[9] Subsequently,
Liu[10] and Rombouts[11] respectively synthesized 2,1-
borazaronaphthalenes and 2,1-borazaroquinolines which were
performed with strict conditions or multiple steps (Scheme 1).
Subsequently, significant progresses in this field had been
achieved by the groups of Paetzold, Ashe, Piers, Cui, and so
1.5 equiv, the yield was increased to 80% (entry 2). The solvents
were evaluated and PhMe was proved to be the best solvent for
this process with the yield of 89% (entry 8). It should be noted
that the yield was slightly decreased with 1.5 equiv of SiCl4 and
2.0 equiv of Et3N (entry 9). To our delight, the desired product
3aa was obtained in 96% yield when the reaction was carried
out at 60 oC (entry 10). Subsequently, reactions were
respectively conducted in O2 and Ar condition with yields of 92%
and 93% (entry 11-12). After further scanning other fluorophiles,
the improvements of the yield were not detected (entry 13-14).
So the optimized reaction system was established as Table 1,
entry 10.
on.[12] Recently, Molander[13] described
synthesize borazaronaphthalenes from
a
new method to
substituted 2-
aminostyrenes and potassium organotrifluoroborates (Scheme
1). However, the plain and gentle processes for B-N containing
heterocycles formation were still very rare. Herein, we have
developed a metal-free method to synthesize fused substituted
4,5-borazaropyrrolo[1,2-a]quinolines with 1-(2-aminophenyl)py-
rroles and potassium organotrifluoroborates.
With the optimized condition in hand, the scope of 1-(2-
aminophenyl)pyrrole was examined firstly and results were
illustrated in Table 2.
aminophenyl)pyrroles
A
variety of substituted 1-(2-
reacted with potassium
Z. An, M. Wu, J. Kang, J. Ni. Z. Qi, B. Yuan and Prof. Dr. R. Yan
State Key Laboratory of Applied Organic Chemistry, Key laboratory of
Nonferrous Metal Chemistry and Resources Utilization of Gansu Province,
Department of Chemistry, Lanzhou University, Lanzhou, Gansu, China.
E-mail: yanrl@lzu.edu.cn
phenyltrifluoroborates smoothly and furnished the desired
products in high yields. Moreover, substituted groups, such as -
Me, -OMe, -Cl, -F, on the aryl ring did not have significant
influence on the formation of products 3ba-3ha. However, lower
yield of 3ia was observed because of the strong electorn-
withdrawing nitrile group.
Then the synthesis of azaborines was further expanded to
the range of substituted potassium aryltrifluoroborates (Table 3).
The potassium aryltrifluoroborates bearing electron-donating
and electron-withdrawing groups were tolerated well under the
Supporting information for this article is given via a link at the end of the
document.
For internal use, please do not delete. Submitted_Manuscript
This article is protected by copyright. All rights reserved.

10.1002/ejoc.201701790
European Journal of Organic Chemistry
COMMUNICATION
Table 1. Optimization of reaction conditions[a]
.
Table 3. Scope of organotrifluoroborates.
Fluorophile
(equiv)
Et3N
(equiv)
Temp
(oC)
Yield
(%)[b]
Entry
Solvent
PhMe/CH3CN
(1:1)
SiCl4 (2.0)
SiCl4 (2.0)
1
2
1.0
1.5
25
80
65
80
PhMe/CH3CN
(1:1)
3
4
SiCl4 (2.0)
SiCl4 (2.0)
SiCl4 (2.0)
SiCl4 (2.0)
SiCl4 (2.0)
SiCl4 (2.0)
SiCl4 (2.0)
SiCl4 (2.0)
SiCl4 (2.0)
CH3CN
Xylene
PhCl
1.5
1.5
1.5
1.5
1.5
1.5
2.0
1.5
80
80
80
80
80
80
80
60
84
56
5
72
6
DMF
Trace
34
7
1,2-DCE
PhMe
PhMe
PhMe
8
89
9
80
10
96
PhMe
PhMe
1.5
1.5
60
60
93[c]
92[d]
11
12
13
SiCl4 (2.0)
BCl3(1 M in
CH2Cl2, 2.0)
BF3·OEt2
(2.0)
Table
4.
Scope
of
substituted
1-(2-aminophenyl)pyrroles
and
PhMe
PhMe
1.5
1.5
60
60
73
40
aromatictrifluoroborates.
14
[a] Reaction conditions: 1a (0.3 mmol), 2a (0.33 mmol), Et3N (0.45 mmol),
fluorophile (0.6 mmol), solvent (2 mL), 4 h, air. [b] Yields of isolated products.
[c] Under O2 condition. [d] Under Ar condition. Entry in bold highlights
optimized reaction conditions, and the reaction time was monitored by TLC.
Table 2. Scope of substituted 1-(2-aminophenyl)pyrroles.
optimized condition, generating desired products in moderate to
good yields (3ab,3ad-3an). Obviously, the steric hindrance had
a distinct impact on the reaction and the desired compound 3ac
was obtained with only 30% yield. Substrate 2k with a strong
electron-withdrawing group was not transformed to the desired
product, which may be due to the electronic effect. The thienyl-
substituted potassium trifluoroborate was also palyed well in this
For internal use, please do not delete. Submitted_Manuscript
This article is protected by copyright. All rights reserved.

10.1002/ejoc.201701790
European Journal of Organic Chemistry
COMMUNICATION
transformation, generating 3al in 64% yield. What’s more,
aliphatic potassium trifluoroborates 2m-2o were also explored in
this process and gave products in 30-88% yields (3am-3ao).
In order to expand the substrate scope, further investigations
were performed to evaluate substituted 1-(2-aminophenyl)-
pyrroles and potassium organotrifluoroborates (Table 4). The
transformations were proceeded soomthly and desired products
were obtained with high yields, especially 3bb, 3ci, and 3fj.
When more challenging substrate 2-(1H-indol-1-yl)aniline was
subjected to standard condtions, only trace amount of 4aa was
detected.
3aa
am
3bd
3ca
3ci
3ed
3fj
3ia
1.0
0.8
0.6
0.4
0.2
0.0
280
300
320
340
360
380
400
nm
On the basis of our experiments and previous reports,[14]
a
plausible mechanism for the approach is outlined in Scheme 2.
Firstly, the potassium phenyltrifluoroborate is transformed to
corresponding active organodichloroborane I with SiCl4. Then,
intermediate II is formed from the reaction of 1a and I via B-N
bond formtion.[15] Finally, the intermediate II is converted to
desired product 3aa by attack of pyrrole double bond to boron.
To probe the optical properties of these products, we chose
product 3fj as model substrate for this experiment. Firstly,
spectral characteristics of 3fj were investigated in several
solvents: PhMe, THF, DCM, MeCN, and EtOH. The result
was summarized in Figure 1. As demonstrated in Figure 1,
3aa
3am
3bd
3ca
3ci
3ed
3fj
3ia
1.0
0.8
0.6
0.4
0.2
0.0
300
350
400
450
500
550
600
nm
Figure 2. Normalized absorption and fluorescence emission spectra of
complexes 3aa, 3am, 3bd, 3ca, 3ci, 3ed, 3fj, and 3ia in MeCN at 10.0
μM.
Table 5. Optical properties of 3aa, 3am, 3bd, 3ca, 3ci, 3ed, 3fj, 3ia and 5aa[a]
.
Stokes
shift (nm)
Compound
3aa
λabs (nm)
317
λem (nm)
396
ε (M-1cm-1)
19800
17500
17700
28700
25300
15200
32900
18900
33300
Φ[b]
79
28
75
84
74
68
113
50
93
0.46
0.42
0.48
0.55
0.57
0.42
0.38
0.39
0.55
Scheme 2. Proposed mechanism.
3am
3bd
3ca
314
342
325
400
DCM
THF
1.0
332
416
PhMe
MeCN
EtOH
0.8
3ci
332
406
0.6
0.4
0.2
0.0
3ed
324
392
3fj
328
434
3ia
334
384
300
350
400
5aa
357
450
nm
[a] Photophysical properties were measured in MeCN at 10.0 μM. [b] The
fluorescence quantum yields were calculated in MeCN using quinine sulfate in
0.05 M H2SO4 as the standard.
DCM
THF
PhMe
MeCN
EtOH
1.0
0.8
0.6
0.4
0.2
0.0
the product 3fj showed an absorption maximum at 328 nm
and solvents had no influence on UV absorption band of 3fj
Nevertheless, the increasing polarity of solvents led to a
red-shift in the fluorescence emission bands. For example,
the emission maximum of 3fj in PhMe emerged at 401 nm
and red-shifted to 433 nm in MeCN.
.
Subsequently, absorption and fluorescence emission spectra
of 3aa, 3am, 3bd, 3ca, 3ci, 3ed, 3fj and 3ia were also evaluated
in MeCN. As shown in Table 5 and Figure 2, compounds 3bd,
3ca, 3ci, and 3fj exhibited bathochromic shifts compared with
350
400
450
500
550
600
nm
Figure 1. Normalized absorption and fluorescence emission spectra
of complex 3fj in DCM, THF, PhMe, MeCN, and EtOH at 10.0 μM.
For internal use, please do not delete. Submitted_Manuscript
This article is protected by copyright. All rights reserved.

10.1002/ejoc.201701790
European Journal of Organic Chemistry
COMMUNICATION
Table 6. Calculated excited wavelength (λ) and oscillator strengths (ƒ) for
component 3fj of selected transition energies.
Orbitals
Compound
State[a]
E(eV)
λ(nm)
ƒ [b]
(coefficient)[c]
3fj
S1
S2
S3
3.7787
4.1886
4.4603
328.11
296.00
277.97
0.2023
0.1317
0.3126
H>L(97%)
H-1>L(42%),
H>L+1(52%)
H-1>L(52%),
H>L+1(41%)
[a] Excited state. [b] Oscillator strength. [c] MOs involved in the transitions.
Calculation was performed at the PBE0/6-311+G(d,p) level in MeCN.
3bd, 3ed, and 3aa, 3ca, 3am, 3ci, respectively. As can be
deduced from Figure 4, for these complexes, LUMO electronic
distribution are almost identically global, whereas HOMO
electronic distribution is mainly on the large π-system. In case of
3fj, which (trifluoromethyl)benzene group is introduced at the
boron atom, HOMO is localised on the π-system and HOMO-1
Figure 3. The relative energies of the frontier orbitals of 3aa, 3ca, 3ia, 3am,
3ci, 3fj, 3bd and 3ed, calculated with B3LYP/6-31G(d) level.
compound 3aa and these compounds showed strong blue
fluorescence at 400-434 nm. In absorption and emission bands,
3fj with electron-withdrawing group showed 11 nm and 38 nm
red-shifts respectively, which was consistent with a smaller
HOMO-LUMO gap in 3fj vs 3aa in figure 3. Fluorescence
quantum yields of these products were also detected and the
quantum yields were moderate (0.38-0.57) in MeCN. At the
same time, the photophysical properties of 4-phenylpyrrolo[1,2-
a]quinoline 5aa[16] were investigated which showed more
obvious redshift compared with 3aa.
electronic
distribution
could
extend
to
the
(trifluoromethyl)benzene group. And the HOMO-LUMO energy
of 3fj is the lowest from Figure 3. For complex 3fj, the transitions
with relatively stronger oscillator strength between the first and
third are mixed HOMO→LUMO and HOMO-1→LUMO, HOMO→
LUMO+1 transitions. It is also apparent that the third lowest
transition is rather close-lying in energy/wavelength.
Multicenter bond order[18] could be used to evaluate
aromaticity and its positive value indicates that the ring would
have aromaticity (Table S1). The computational results show
that the vaules of ring 1 and 3 are positive, suggesting the five-
membered ring 1 and six-membered ring 3 are aromatic nucleus
with conjugated π electronic structure. While, the ring 2 is also
one aromatic ring with small positive value. Finally, the three
rings (ring 1, 2 and 3) would form one large conjugate structure.
In conclusion, we have described a synthetic approach to 4,5-
borazaropyrrolo[1,2-a]quinolines via cyclization of 1-(2-
aminophenyl)pyrroles and organotrifluoroborates in a facile
procedure. In this transformation, a wide functional group can be
tolerated and desired products are obtained in moderate to good
yields. Meanwhile, the optical properties and DFT calculation
about B-containing products are investigated gaining a moderate
result. Furthermore, the study allows us to find that chemical
modification at the boron atom leads to corresponding blue-
shifts or red-shifts in the absorption and emission bands. Due to
attractive spectral characteristics, resultant azaborines have
tremendous potential applications in biotechnology and material
science.
To investigate the influence of structural modification on the
spectroscopic and electronic properties of the boron-complexes,
ground-state geometry optimizations were performed by DFT
with B3LYP functional and 6-31(G) basis set by using the
Gaussian 09 software package.[17] The PBE0 functional was
preferred for using in time-dependent density functional theory
(TD-DFT) calculations with 6-311+G(d,p) basis sets. Figure 4
and Figure 1S showed the frontier molecular orbitals of 3ia, 3fj,
Experimental Section
General procedure for the synthesis of 4,5-Borazaropyrrolo[1,2-
a]quinolines derivatives:
2-(1H-pyrrol-1-yl)aniline 1a (1 equiv, 0.3 mmol), potassium
organotrifluoroborate 2a (1.1 equiv, 0.33 mmol), Et3N (1.5 equiv, 0.45
mmol), SiCl4 (2.0 equiv, 0.6 mmol), toluene (2 mL) were added to a
screw-cap vial with a stir bar. The reaction mixture was heated to 60 °C
under vigorous stirring for 4 h. Then the reaction mixture was cooled to
room temperature and extracted with ethyl acetate and water. The
combined organic phase was dried over anhydrous Na2SO4. The solvent
Figure 4. The nodal patterns of HOMO-1, HOMO, LUMO and LUMO+1 of 3ia,
3fj, 3bd and 3ed, calculated with B3LYP/6-31G(d) level.
For internal use, please do not delete. Submitted_Manuscript
This article is protected by copyright. All rights reserved.

10.1002/ejoc.201701790
European Journal of Organic Chemistry
COMMUNICATION
[7]
[8]
M. J. D. Bosdet, C. A. Jaska, W. E. Piers, T. S. Sorensen, M. Parvez,
Org. Lett. 2007, 9, 1395.
was evaporated in vacuo and the crude product was purified by column
chromatography, eluting with petroleum ether/EtOAc (20:1) to afford the
desired 3aa.
a) G. A. Molander, S. R. Wisniewski, J. Org. Chem. 2014, 79, 6663; b)
A. R. Goldberg, B. H. J. Northrop, Org. Chem. 2016, 81, 969; c) C. A.
Slabber, C. D. Grimmer, R. S. Robinson, J. Organomet. Chem. 2013,
723, 122; d) S. W. Hadebe, S. Sithebe, R. S. Robinson, Tetrahedron
2011, 67, 4277; e) D. J. H. Emslie, W. E. Piers, M. Parvez, Angew.
Chem. Int. Ed. 2003, 42, 1251; f) G. Kaupp, M. R. N. Jamal, V.
Stepanenko, Chem. Eur. J. 2003, 9, 4156; g) E. Nyilas, A. H. Soloway,
J. Am. Chem. Soc. 1959, 81, 2681; h) H. Noda, J. W. Bode, J. Am.
Chem. Soc. 2015, 137, 3958; i) M. F. Hawthorne, J. Am. Chem. Soc.
1961, 83, 831.
Acknowledgements
This work was supported by National Natural Science
Foundation of China (21672086), Gansu Province Science
Foundation for Youths (1606RJYA260) and the Fundamental
Research Funds for the Central Universities (lzujbky-2016-39).
[9]
M. J. S. Dewar, R. Dietz, J. Chem. Soc. 1959, 2728.
[10] G. E. Rudebusch, L. N. Zakharov, S.-Y. Liu, Angew. Chem. Int. Ed. 2013,
52, 9316.
Keywords: mild condition • fused 4,5-borazaropyrrolo[1,2-
a]quin- olines • optical properties
[11]
[12]
M. R. S. Casado, M. C. Jiménez, M. A. Bueno, M. Barriol, J. E.
Leenaerts, C. Pagliuca, C. M. Lamenca, A. I. D. Lucas, A. García, A. A.
Trabanco, F. J. R. Rombouts, Eur. J. Org. Chem. 2015, 5221.
a) P. Paetzold, C. Stanescu, J. R. Stubenrauch, M. Bienmuller, U.
Englert, Z. Anorg. Allg. Chem. 2004, 630, 2632; b) A. J. Ashe, X.-D.
Fang, Org. Lett. 2000, 2, 2089; c) C. A. Jaska, D. J. H. Emslie, M. J. D.
Bosdet, W. E. Piers, T. S. Sorensen, M. Parvez, J. Am. Chem. Soc.
2006, 128, 10885; d) X.-W. Liu, P.-B. Wu, J.-F. Li, C.-M. Cui, J. Org.
Chem. 2015, 80, 3737.
[1]
a) G. A. Molander, S. R. Wisniewski, K. M. Traister, Org. Lett. 2014, 16,
3692; b) G. A. Molander, S. R. Wisniewski, J. Amani, Org. Lett. 2014,
16, 5636; c) B. Glaser, H. Noth, Angew. Chem. Int. Ed. 1985, 24, 416;
d) G. A. Molander, J. Org. Chem. 2015, 80, 7837; e) M. J. S. Dewar, R.
Dietz, V. P. Kubba, A. R. Lepley, J. Am. Chem. Soc. 1961, 83, 1754;
a) D. J. H. Emslie, W. E. Piers, M. Parvez, Angew. Chem. Int. Ed. 2003,
42, 1252; b) C. A. Jaska, D. J. H. Emslie, M. J. D. Bosdet, W. E. Piers,
T. S. Sorensen, M. Parvez, J. Am. Chem. Soc. 2006, 128, 10085; c) E.
R. Abbey, L. N. Zakharov, S.-Y. Liu, J. Am. Chem. Soc. 2011, 133,
11508; d) G. H. M. Davies, G. A. Molander, J. Org. Chem. 2016, 81,
3771; e) . C t a .-M. . Ma i e, K. Boknevitz, B. Li, E.
R. Abbey, A. Dargelos, A. Graciaa, S.-Y. Liu, J. Am. Chem. Soc. 2014,
136, 11813; f) A. N. Brown, L. N. Zakharov, T. Mikulas, D. A. Dixon, S.-
Y. Liu, Org. Lett. 2014, 16, 3340; g) G. A. Molander, J. Amani, S. R.
Wisniewski, Org. Lett. 2014, 16, 6024; h) M. Jouffroy, G. H. M. Davies,
G. A. Molander, Org. Lett. 2016, 18, 1606.
[2]
[13] G. H. M. Davies, Z.-Z. Zhou, M. Jouffroy, G. A. Molander, J. Org. Chem.
2017, 82, 549.
[14] a) B. J. Kim, D. S. Matteson, Angew. Chem. Int. Ed. 2004, 43, 3056; b)
D. S. Matteson, G. Y. Kim, Org. Lett. 2002, 13, 2153.
[15]
S. R. Wisniewski, C. L. Guenther, O. A. Argintaru, G. A. Molander, J.
Org. Chem. 2014, 79, 365.
[16] D. I. Chai, M. Lautens, J. Org. Chem. 2009, 74, 3054.
[17] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb,
J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A.
Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F.
Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K.
Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O.
Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr.;, J. E. Peralta, F.
Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N.
Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.
C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M.
Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R.
Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C.
Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski,
G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels,
O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox and R.
Gaussian 09, A. 02, Gaussian, Inc.: Wallingford CT, 2009.
[3]
[4]
a) D. H. Knack, J. L. Marshall, G. P. Harlow, A. Dudzik, M. Szaleniec,
S.-Y. Liu, J. Heider, Angew. Chem. Int. Ed. 2013, 52, 2599; b) F. J. R.
Rombouts, F. Tovar, N. Austin, G. Tresadern, A. A. Trabanco, J. Med.
Chem. 2015, 58, 9287; c) G. A. Patani, E. J. LaVoie, Chem. Rev. 1996,
96, 3147; d) L. Liu, A. J. V. Marwitz, B. W. Matthews, S.-Y. Liu, Angew.
Chem. Int. Ed. 2009, 48, 6817.
a) P. L. Chen, X. B. Wang, D. H. Tang, Z. Zhen, J. C. Zhang, X. H. Liu,
Dyes Pigm. 2001, 48, 85; b) C. G. Claessens, D. G. Rodriguez, T.
Torres, Chem. Rev. 2002, 102, 835; c) J. Wang, Q. H. Wu, C. J. Yu, Y.
Wei, X. L. Mu, E. H. Hao, L. J. Jiao, J. Org. Chem. 2016, 81, 11316; d)
F. Qiu, F. Zhang, R. Z. Tang, Y. B. Fu, X. Y. Wang, S. Han, X. D.
Zhuang, X. L. Feng, Org. Lett. 2016, 18, 1398.
[18] M. Giambiagi, M. S. de Giambiagi, K. C. Mundim, Struct. Chem. 1990, 1,
423.
[5]
[6]
M. S. Goncalves, Chem. Rev. 2009, 109, 190.
a) P. G. Campbell, A. J. V. Marwitz, S.-Y. Liu, Angew. Chem. Int. Ed.
2012, 51, 6074; b) F.-Y. Sun, L.-L. Lv, M. Huang, Z.-H. Zhou, X.-D.
Fang, Org. Lett. 2014, 16, 5024.
For internal use, please do not delete. Submitted_Manuscript
This article is protected by copyright. All rights reserved.

10.1002/ejoc.201701790
European Journal of Organic Chemistry
COMMUNICATION
COMMUNICATION
Zhenyu An, Mingzhong Wu, Jie Kang,
Jixiang Ni, Zhenjie Qi, Bingxiang Yuan
and Rulong Yan*
Page No. – Page No.
Synthesis of Fused B-containing
Heterocyclic Compounds and Studied
their Relevent Optical Properties
A new B-containing heterocyclic compound ! A series of azaborines were
prepared through 1-(2-aminophenyl)pyrroles and organotrifluoroborates in one-pot
manner. The optical properties of these azaborines were investigated and the
attractive photornetrics could be applied in many scientific fields.
For internal use, please do not delete. Submitted_Manuscript
This article is protected by copyright. All rights reserved.