BTADCI Promoted One-pot Synthesis of 14-aryl-14H-dibenzo [a, j] Xanthenes

Article abstract of DOI:10.1002/jhet.3162

A convenient eco-friendly one-pot synthesis of 14-aryl-14H-dibenzo [a, j] xanthenes were developed by the condensation of aromatic aldehydes and β-naphthol with BTADCI (Benzyltrimethylammonium dichloroiodate) as catalyst under solvent free conditions and microwave irradiation with much more rate accelerations and afford very good yields. Developed protocols involve mild reaction conditions, simple isolation of derivatives with inexpensive reagents.

Full text of DOI:10.1002/jhet.3162

Month 2018
BTADCI Promoted One-pot Synthesis of 14-aryl-14H-dibenzo
[a, j] Xanthenes
Ramakanth Pagadalaa,b
and Uppalaiah Kusampallyc
*
aDepartment for Management of Science and Technology Development, Ton Duc Thang University,
Ho Chi Minh City, Vietnam
bFaculty of Applied Sciences, Ton Duc Thang University, Ho Chi Minh City, Vietnam
cDepartment of Chemistry, Osmania University (O.U), Hyderabad 500 007, T. S., India
*
E-mail: ramakanth.pagadala@tdt.edu.vn
Received January 5, 2018
DOI 10.1002/jhet.3162
Published online 00 Month 2018 in Wiley Online Library (wileyonlinelibrary.com).
A convenient eco-friendly one-pot synthesis of 14-aryl-14H-dibenzo [a, j] xanthenes were developed by
the condensation of aromatic aldehydes and β-naphthol with BTADCI (Benzyltrimethylammonium
dichloroiodate) as catalyst under solvent free conditions and microwave irradiation with much more rate
accelerations and afford very good yields. Developed protocols involve mild reaction conditions, simple
isolation of derivatives with inexpensive reagents.
J. Heterocyclic Chem., 00, 00 (2018).
INTRODUCTION
for the amalgamation of 14-aryl-14H-dibenzo [a, j]
xanthenes subsidiaries by one-pot buildup of 2-naphthol
and aryl aldehydes catalyzed by extended graphite under
solvent-free conditions [9]. Shaterian et al., have declared
ferric hydrogen sulfate and aluminum hydrogen sulfate
Al(HSO4)3 catalyzed the essential one-pot union of
14-aryl-14H-dibenzo [a, j] xanthenes subordinates under
warm and solvent-free conditions by development of
2-naphthol and substituted benzaldehyde [10,11]. The
union of dibenzoxanthenes by the buildup of aldehydes
with β-naphthol within the sight of CBr4 as an impetus
has been reported [12]. Polyvinyl poly pyrrolidone-
bolstered boron trifluoride (PVPP-BF3) is a gentle
and productive impetus for the union of 14-aryl-14H-
dibenzo [a, j] xanthenes and bis(naphthalene-2-yl-sulfane)
subsidiaries under solvent-free system [13,14].
Recoverable heterogeneous AgI nanoparticles effectively
catalyzed the one-pot union of 14-aryl-14H-dibenzo [a, j]
xanthenes through multi-segment response of aldehydes
and 2-naphthol under solvent-free conditions [15].
Microwave helped green mix of dibenzo [a, j] xanthenes
using a capable, proficient, and eco-pleasing procedure for
the mix of 14-aryl-14H-dibenzo [a, j] xanthenes has been
refined by methods for p-dodecylbenzenesulfonic acid
(DBSA) under solvent-free microwave conditions [16],
[H-NMP][HSO4] as a Brønsted acidic ionic fluid under
solvent-free conditions, at 110°C [17], sulfonic corrosive
functionalized silica (SiO2-Pr-SO3H) under solvent free
Condensation reactions are a set of eco-friendly
reactions assisted with the elimination of simple
molecules such as water or ammonia before yielding
products. Xanthenes synthesis is simple condensation
reaction that has attracted considerable attention of
organic and biochemists in recent past because of its
simplicity. In these reactions, isolation of intermediate is
not required before the end product is obtained; this
reduces time and saves both energy and raw materials.
Benzoxanthenes are an extraordinary class of xanthenes,
which have an extensive variety of organic and helpful
properties, for example, antibacterial, antiviral exercises,
and furthermore they are hopefuls in photodynamic
therapy [1–3]. Xanthenes dyes tend to be fluorescent,
yellow to pink to bluish red, brilliant dyes.
Moreover, benzoxanthenes are utilized as dyes in laser
technologies [4] and in fluorescent materials [5–7]. The
synthesis of benzoxanthenes schematically represented
(Scheme 1), which are obtained by the buildup of
aldehydes with β-naphthol by Cyclo-dehydration within
the sight of a variety of impetuses, for example, AcOH–
H2SO4, p-TSA, MeSO3H, sulfamic corrosive, ionic fluid,
iodine, heteropolyacid, silica sulfuric corrosive,
Amberlyst-15, cyanuric chloride, LiBr, Yb(OTf)3,
Sc[N(SO2C8F17)2]3, NaHSO4, and Al(HSO4)3 [8]. Geng-
Chen Li has developed a convenient eco-friendly strategy
© 2018 Wiley Periodicals, Inc.

R. Pagadala and U. Kusampally
Vol 000
Scheme 1. BTADCI Promoted One-pot synthesis of 14-aryl-14H-dibenzo [a, j] xanthenes.
conditions [18,19]. The one-pot combination of 14-aryl-
14H-dibenzo [a, j] xanthenes catalyzed by assignment
naphthol to give target molecule assisted by the elimination
of water molecule. The synthesized xanthene derivatives
were fullycharacterized by FTIR, 1H NMR, 13C NMR,
and mass spectrometer (Supplementary data).
particular ionic fluid
a Brønsted-acidic undertaking
particular ionic fluid, 1-methyl-3-propane sulfonic-
imidazolium hydrosulfate ([MIMPS] HSO4), via the
one-pot condensation of β-naphthol with aliphatic or
sweet-smelling aldehydes [20]. All responses are
performed without dissolvable in generally short response
times in great to high yields [21]. This prompted a
sensational increment in the quantity of distributions
utilizing MW in natural synthesis [22–24].
EXPERIMENTAL
General remarks.
All chemicals used were reagent
grade and were used as received without further
purification. 1H NMR and 13C NMR spectra were
recorded at 25°C at 300 MHz and 75 MHz (Bruker
Avance, Switzerland) instrument, respectively, using TMS
as internal standard. Chemical shifts are given in parts
per million (ppm). The FT-IR spectroscopy of samples
was carried out on a Perkin Elmer (Maryland, USA) pre-
cisely 100 FT-IR spectrometer in the 400–4000 cmÀ1
region. LCMS mass spectra were recorded on a MASPEC
low resolution mass spectrometer operating at 70 eV. Ele-
mental analyses were carried out using a Perkin-Elmer
CHNS Elemental Analyzer model 2400. Melting points
are uncorrected and were recorded on a hot stage melting
point apparatus Ernst Leitz Wetzlar, Germany. The
MW-assisted synthesis of titled compounds was carried
out in a CEM – 908010 (Smith Farm Rd, Mathews, N.C-
28105, US), bench mate model, 300 watts laboratory
MW reactor. Reactions were monitored, and the purity of
products was checked out on thin layer chromatography
(TLC) on aluminum-backed plates coated with Kieselgel
60 F254 silica gel, visualizing the spots under ultraviolet
light and iodine chamber.
As expanding natural cognizance in synthetic research and
industry, the test for a maintainable situation consistently
calls for clean procedures [25]. Which are fairly long to
grow this kind of pair process that would allow the buildup
of the in situ produced orthoquninonemethide with
nucleophile other than phenols, naphthol compounds using
BTADCI as a catalyst until now has not been explored in
synthetic organic chemistry. In our attempt to explore the
role, BTADCI is mild and efficient Lewis acid catalyst. A
major concern to overcome such problems in organic
synthesis has considered the use of solvent free and
microwave irradiation as a source of energy.
RESULTS AND DISCUSSION
In view of our ongoing interest in green chemistry, the
author has taken up solvent free and microwave
irradiated one-pot synthesis of 14-aryl-14H-dibenzo [a, j]
xanthenes derivatives using condensation of aromatic
aldehydes and β-naphthol with BTADCI. The reaction
was completed in 70 to 90 min in solvent free condition
at 110°C and 8 to 10 min in microwave conditions
(Table 1) to obtain14-(3-Fluorophenyl)-14H-dibenzo [a, j]
xanthenes (Scheme 1).
The most plausible mechanism of is proposed as shown
in Scheme 2. First step involves proton abstraction by the
arylaldehyde leading to the formation of aryl oxocarbenium
ion intermediate (II), which in turn reacts with β-naphthol
General method for the synthesis of xanthenes derivatives
(3a–j).
The reaction mixture was of β-naphthol
(2 mmol), 3-fluorobenzaldehyde (1 mmol), and BTADCI
(60 mg) was heated at 110°C until completion, the
reaction mixture was cooled to room temperature and
extracted in to ethyl acetate and washed with 15%
Na2CO3; the resultant mixture was purified by column
chromatography using silica gel (60–120 mesh size) and
recrystallized in aqueous EtOH (15%).
in
a condensation step to afford naphthyloxonium
intermediate (III) followed by the removal of water
molecule as shown in Scheme 2. The naphthyloxonium
intermediate (III), thus, formed reacts with one more β-
General method for the synthesis of xanthenes derivatives
under microwave irradiation (3a–j).
A mixture of
β-naphthol (2 mmol), aldehydes (1 mmol), and BTADCI
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2018
BTADCI Promoted One-pot Synthesis of Xanthenes
Table 1
The synthesis of 14-aryl-14H-dibenzo [a. j] xanthene derivative by BTADCI.
S. No.
Aldehydes
Products (3a–j)
Solvent free
Micro wave
1
2
3
4
5
6
7
8
4-F-C6H4-CHO
2-NO2-C6H4-CHO
4-Me-C6H4-CHO
4-OMe-C6H4-CHO
4-OH-C6H4-CHO
2-Cl-C6H4-CHO
4-Cl-C6H4-CHO
C6H4-CHO
4-Br-C6H4-CHO
3-OH-C6H4-CHO
3-Br-C6H4-CHO
3-OMe-C6H4-CHO
3a
3b
3c
3d
3e
3f
3g
3h
3i
75
70
85
82
85
80
80
80
75
80
79
80
85
80
95
93
95
95
90
90
90
95
94
95
9
10
11
12
3j
3k
3l
Reaction times: Microwave 8–10 min; solvent free 70–90 min; isolated yields.
Scheme 2. Proposed mechanism of 14-aryl-14H-dibenzo [a, j] xanthenes promoted by BTADCI.
(60 mg) was placed in a laboratory microwave oven (BPL,
800 T model) on a silica gel solid support and heated at
300 W for the appropriate time. The product isolation
and purification methods are same as aforementioned and
recrystallized in aqueous EtOH (15%) to obtain pure
product.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

R. Pagadala and U. Kusampally
Vol 000
14-(4-FlroPhenyl)-14H-dibenzo [a,j] xanthenes (3a).
White solid; mp 230–232°C; 1HNMR (400 MHz, CDCl3):
δ = 6.49 (s, 1H), 6.78 (t, J = 8.4 Hz, 2H), 7.38–7.47
(m, 6H), 7.55 (t, J = 8.0 Hz, 2H), 7.77 (m, 4H), 8.31
(d, J = 8.4 Hz, 2H); 13CNMR (100 MHz, CDCl3):
δ = 37.1, 115.1, 115.4, 117.1, 118.0, 122.4, 124.3, 126.8,
128.8, 128.9, 129.5, 129.6, 131.0, 131.3, 148.7; IR (KBr
12H), 9.18 (d, J = 8.4 Hz, 2H); 13CNMR (100 MHz,
CDCl3): δ = 33.5, 116.9, 117.0, 122.3, 123.3, 125.8,
126.7, 126.8, 127.5, 128.0, 128.5, 129.0, 129.8, 130.7,
142.5, 147.9; IR (KBr cmÀ1): 3069, 1695, 1591, 1430,
1243, 747, 692; EI-MS: m/z (%) = 394 (M+). Anal.
Calcd for C27H17ClO: C, 82.54; H, 4.36; Cl, 9.02.
Found: C, 82.60; H, 4.32, Cl, 9.04.
14-(4-Chlorophenyl)-14H-dibenzo [a, j] xanthenes (3g).
1
cmÀ ): 3068, 2926, 1591, 1457, 1396, 1243, 1157, 1087,
Yellow solid; mp 289–291°C; 1HNMR (400 MHz,
CDCl3): δ = 6.46 (s, 1H), 7.08 (d, J = 8.0 Hz, 2H),
7.42–7.57 (m, 8H), 7.78–7.84 (m, 4H), 8.30 (d,
J = 8.0 Hz, 2H); 13CNMR (100 MHz, CDCl3): δ = 37.4,
116.8, 118.0, 122.4, 124.3, 126.9, 128.6, 128.9, 129.0,
129.4, 131.1, 131.3, 132.1, 143.4, 148.7; (IR KBr
cmÀ1): 3066, 1622, 1514, 1456, 1397, 1245, 1209,
1065, 959, 812, 775, 746. EI-MS: m/z (%) = 392 (M+).
Anal. Calcd for C27H17ClO: C, 82.54; H, 4.36. Found:
957, 809, 742; EI-MS: m/z (%) = 376 (M+); Anal. Calcd
for C27H17FO: C, 86.15; H, 4.55; F, 5.05. Found: C,
86.12; H, 4.41, F, 5.01.
14-(2-Nitrophenyl)-14H-dibenzo [a, j] xanthenes (3b).
Yellow solid; mp 211–213°C; 1HNMR (400 MHz,
CDCl3): δ = 7.06–7.23 (m, 2H), 7.41–7.44 (m, 2H),
7.47–7.83 (m, 11H), 8.51 (d, J = 8.4 Hz, 2H); 13CNMR
(100 MHz, CDCl3): δ = 32.5, 117.5, 118.0, 122.5, 124.6,
124.9, 127.3, 127.5, 128.7, 129.4, 130.9, 131.7, 132.2,
134.1, 140.8, 147.0, 149.3; IR (KBr, cmÀ1): 3400, 3057,
1625, 1593, 1397,, 1305, 817, 750; EI-MS: m/z
(%) = 418 (M+); Anal. Calcd for C27H17NO3: C, 80.38;
H, 4.25; N, 3.47, Found: C, 80.29; H, 4.26, N, 3.53.
14-(4-Methylphenyl)-14H-dibenzo [a, j] xanthenes (3c).
Yellow solid; mp 221–223°C; 1HNMR (400 MHz,
CDCl3): δ = 2.12 (s, 3H), 6.45 (s, 1H), 6.94 (d,
J = 8.0 Hz, 2H), 7.38–7.42 (m, 4H), 7.46 (d, J = 8.8 Hz,
2H), 7.55–7.59 (m, 2H), 7.77–8.38 (m, 6H); 13CNMR
(100 MHz, CDCl3): δ = 20.8, 37.6, 117.4, 118.0, 122.7,
124.2, 126.7, 128.0, 128.7, 128.7, 129.1, 131.1, 131.4,
135.8, 142.1, 148.7; IR (KBr, cmÀ1): 3073, 1625, 1513,
1435, 1258, 1123, 1086, 966, 841, 813, 744; EI-MS: m/z
(%) = 372 (M+); Anal. Calcd for C28H20O: C, 90.29; H,
5.41. Found: C, 90.36; H, 5.46.
C, 82.60; H, 4.39.
14-Phenyl-14H-dibenzo [a, j] xanthenes (3h). Off-white
solid; mp 185–187°C; 1HNMR (400 MHz, CDCl3): δ
6.45 (s, 1H), 6.96 (t, J = 7.2 Hz, 1H), 7.12 (t,
J = 7.2 Hz, 2H), 7.37–7.58 (m, 8H), 7.74–7.81 (m, 4H),
8.34 (d, 2H); 13CNMR (100 MHz, CDCl3): δ = 38.0,
117.3, 118.0, 122.6, 124.2, 126.3, 126.7, 128.2, 128.4,
128.7, 128.8, 131.0, 131.4, 148.7; IR (KBr cmÀ1): 3070,
1585, 1445, 1250, 1080, 965; EIMS, 70 eV, m/z: 358
(M+); Anal. Calcd for C27H18O: C, 90.47; H, 5.06.
Found: C, 90.43; H, 5.08.
14-(4-Bromophenyl)-14H-dibenzo [a, j]-xanthene (3i).
Off-white solid; mp 295–296°C; 1HNMR (400 MHz,
CDCl3): δ 8.32 (d, J = 8.4 Hz, 2H), δ 7.85–7.78 (m, 4H),
δ 7.60–7.55 (m, 2H), δ = 7.48–7.37 (m, 5H), δ 7.25–7.23
(m, 3H), δ 6.46 (s, 1H); 13CNMR (75 MHz, CDCl3): d
147.9, 144.8, 131.2, 130.7, 130.6,130.0, 129.2, 128.6,
127.0, 124.6, 123.2, 119.4, 117.6, 116.8, 36.8; IR (KBr,
cmÀ1): 3056, 2922, 1622, 1590, 1514, 1456, 1392, 1243,
1231, 1207, 1143,1062, 957, 816, 772, 741; EIMS,
14-(4-Methoxyphenyl)14H-dibenzo[a, j]xanthenes (3d).
Off-white solid; mp 203–205°C; 1HNMR (400 MHz,
CDCl3): δ = 3.61 (s, 3H), 6.44 (s, 1H), 6.57–6.67 (m,
2H), 7.38–7.48 (m, 6H), 7.55–7.83 (m, 6H), 8.39 (d,
J = 8.4 Hz, 2H); 13CNMR (100 MHz, CDCl3): δ = 37.1,
55.0, 113.8, 117.5, 118.0, 122.6, 124.2, 126.7, 128.7,
128.8, 129.1, 131.1, 131.4, 137.3, 148.7, 157.8; IR (KBr
cmÀ1): 3062, 1594, 1509, 1458, 1398, 1247, 960, 814,
744. EI-MS: m/z (%) = 388 (M+); Anal. Calcd for
C28H20O2: C, 86.57; H, 5.19. Found: C, 86.60; H, 5.23.
14-(4-Hydroxyphenyl)-14H-dibenzo [a, j] xanthenes (3e).
70 eV, m/z: 437 (M+).
14-(3-Hydroxyphenyl)-14H-dibenzo [a, j]-xanthene (3j).
Off-white solid; mp 242–243°C. 1HNMR (400 MHz,
CDCl3): δ 8.37 (d, J = 8.7 Hz, 2H), δ 7.83–7.76 (m, 4H),
δ 7.59–7.54 (m, 2H), δ 7.47–7.37 (m, 4H), δ 7.18 (d,
J = 7.8 Hz, 1H), δ 7.03 (t, J = 8.1 Hz, 1H), δ 6.86 (s,
1H), δ 6.64–6.43 (m, 2H), δ 4.54 (s, 1H); 13CNMR
(100 MHz, CDCl3): d 154.8, 147.9, 145.9, 130.6,
130.2,128.6, 128.1, 128.0, 126.0, 123.5, 121.9, 120.1,
117.2, 116.3, 114.6, 112.8, 37.0; IR (KBr, cmÀ1): 3412,
1588, 1507, 1413, 1258, 1237, 813; EIMS, 70 eV, m/z:
374 (M+); Anal. Calcd for C27H18O2: C, 86.61; H,
4.85. Found: C, 86.58; H, 4.81.
1
Pink solid; mp 139–141°C; HNMR (400 MHz, CDCl3):
δ = 6.43 (s, 1H), 6.57–6.59 (m, 2H), 7.35–7.59 (m, 8H),
7.76–7.83 (m, 4H), 8.35 (d, J = 8.4 Hz, 2H); 13CNMR
(100 MHz, CDCl3): δ = 37.0, 115.2, 117.4, 117.9, 122.6,
124.2, 126.7, 128.7, 128.8, 129.3, 131.0, 131.3, 137.4, 148.6,
153.8; IR (KBr, cmÀ1): 3393, 1596, 1514, 1437, 1404, 1257,
958, 818, 748; EI-MS: m/z (%) = 374 (M+); Anal. Calcd for
C27H18O2: C, 86.61; H, 4.85. Found: C, 86.56; H, 4.82.
14-(2-Chlorophenyl)-14H-dibenzo [a, j] xanthenes (3f).
Off-white solid; mp 178–180°C; 1HNMR (400 MHz,
CDCl3): δ = 7.25 (s, 1H), 7.34 (m, 2H), 7.70–8.28 (m,
14-(3-BromoPhenyl)-14H-dibenzo [a, j] xanthenes (3k).
Off-white solid; m.p. 197–199; 1HNMR (400 MHz,
CDCl3): δ = 6.45 (s, 1H), 7.0–7.13 (m, 2H), 7.41–7.62
(m, 8H), 7.80–8.31 (m, 6H); 13CNMR (100 MHz,
Journal of Heterocyclic Chemistry
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Month 2018
BTADCI Promoted One-pot Synthesis of Xanthenes
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CDCl3): δ = 37.7, 116.5, 118.0, 122.7, 124.3, 126.8, 126.9,
128.9, 129.1, 129.6, 129.9, 131.0, 131.1, 131.2, 147.1,
148.8 IR (KBr cmÀ1): = 3066, 3020, 1628, 1594, 1398,
1249, 810, 740; EI-MS: m/z (%) = 436 (M+); Anal.
Calcd for C27H17BrO: C, 74.15; H, 3.92. Found: C,
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74.17; H, 3.99.
14-(3-Methoxyphenyl)14H-dibenzo[a, j]xanthenes (3l).
Off-white solid; mp 160–162°C; 1HNMR (400 MHz,
CDCl3): δ = 3.63 (s, 3H), 6.46 (s, 1H), 6.51–6.53
(m, 1H), 7.02–7.17 (m, 3H), 7.38–7.83 (m, 10H), 8.38
(d, J = 8.4 Hz, 2H); 13CNMR (100 MHz, CDCl3):
δ = 37.9, 54.9, 110.9, 114.8, 117.9, 120.7, 122.6, 124.1,
126.7, 128.7, 128.8, 129.2, 131.0, 131.4, 146.4, 148.7,
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159.5; IR (KBr cmÀ ): 3015, 2951, 2940, 1594, 1490,
1
1455, 1439, 1400, 1250 cmÀ ; EI-MS: m/z (%) = 388
(M+); Anal. Calcd for C28H20O2: C, 86.45; H, 5.06.
Found: C, 86.58; H, 5.12.
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CONCLUSION
In brief, the authors have developed a convenient eco-
friendly procedure for one-pot synthesis of 14-aryl-14H-
dibenzo [a, j] xanthene derivatives by the condensation of
β-naphthol and aromatic aldehydes catalyzed by BTADCI
under solvent free and micro wave conditions. The
developed methodologies offer advantages such as
excellent yields, shorter reaction times, and low cost of
the catalyst. Thus, the present method provides Green-
Reaction conditions with a simple work-up procedure.
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other authorities of Osmania University, Hyderabad for constant
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet