Synthesis of novel angular diazaphenoxazinone derivatives via palladium catalyzed Buchwald-Hartwig amidation protocols

Article abstract of DOI:10.14233/ajchem.2015.18874

The synthesis of new amido derivatives of angular diazaphenoxazinone via tandem amidation protocol is reported. This was achieved by the condensation of 4,5-diamino-6-hydroxypyrimidine (7) with 2,3-dichloro-1,4-naphthoquinone (8) in anhydrous basic medium to furnish the key intermediate, 11-amino-6-chloro-8,10-diazabenzo[a]phenoxazin-5-one (9). Palladium catalyzed amidation reaction of 11-amino-6-chloro-8,10-diazabenzo[a]phenoxazin-5-one (9) with different amides (12a-c) (benzamide, acetamide, salicylamide and 4-nitrobenzamide) in the presence of palladium(II) acetate, triphenyl phosphine (PPh₃), water and tertiary butanol at 110°C for 3 h gave the new amido derivatives 13a-c. Structures of the new compounds were established by elemental analysis, UV, FTIR, ¹H NMR and ¹³C NMR.

Full text of DOI:10.14233/ajchem.2015.18874

Asian Journal of Chemistry; Vol. 27, No. 8 (2015), 3069-3073
A
SIAN
J
OURNAL OF HEMISTRY
C
http://dx.doi.org/10.14233/ajchem.2015.18874
Synthesis of Novel Angular Diazaphenoxazinone Derivatives via
Palladium Catalyzed Buchwald-Hartwig Amidation Protocols
*
M.E. ODAA, U.C. OKORO and D.I. UGWU
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
*Corresponding author: E-mail: izuchukwu.ugwu@unn.edu.ng
Received: 24 November 2014; Accepted: 18 December 2014;
Published online: 27 April 2015;
AJC-17194
The synthesis of new amido derivatives of angular diazaphenoxazinone via tandem amidation protocol is reported. This was achieved by
the condensation of 4,5-diamino-6-hydroxypyrimidine (7) with 2,3-dichloro-1,4-naphthoquinone (8) in anhydrous basic medium to
furnish the key intermediate, 11-amino-6-chloro-8,10-diazabenzo[a]phenoxazin-5-one (9). Palladium catalyzed amidation reaction of
11-amino-6-chloro-8,10-diazabenzo[a]phenoxazin-5-one (9) with different amides (12a-c) (benzamide, acetamide, salicylamide and
4-nitrobenzamide) in the presence of palladium(II) acetate, triphenyl phosphine (PPh3), water and tertiary butanol at 110 °C for 3 h gave
the new amido derivatives 13a-c. Structures of the new compounds were established by elemental analysis, UV, FTIR, 1H NMR and 13C
NMR.
Keywords: Synthesis, Phenoxazines, Phenoxazinone, Diazaphenoxazinone, Tandem catalysis.
actinomycin D (6) is the most significant member of actino-
mycines which are a class of polypeptide antibiotics isolated
from soil bacteria. Phenoxazines have been reported to show
interesting anti-inflammatory12, multi drug resistance reversal
activity13, prevent human amyloid disorder14, protect neuronal
cells from death by oxidative stress15, antitumor16, antimicro-
bial17, and antiviral activities18. Zuse et al.19 reported 9-benzyli-
dene-naphtho[2,3-b]thiophen-4-ones as novel antimicrotubule
agent. Prinz et al.20 reported N-benzoylated phenoxazines as
inhibitors of tubulin polymerization which implies that the
compounds are potential anticancer agent. Nowakowska-Oleksy
et al.21 reported phenoxazine-based conjugates of semiconducting
and luminescent properties. Raju et al.22 reported the facile
synthesis of phenoxazines via ring opening of benzoxepines.
Thome et al.23 reported the transition-metal-free synthesis of
N-substituted phenoxazines from N-acetylated aryloxy anilides.
Reddy24 reported an improved process for the synthesis of
phenoxazine with antidiabetic properties. Jose and Burgess25
reported the synthesis of benzophenoxazine-based fluorescent
dyes for labeling biomolecules. Hayashi et al.26 reported
phenoxazine derivatives that could suppress infections caused
by herpes simplex virus type-1 and herpes simplex virus type-
2. Shimamoto et al.27 reported novel phenoxazine derivatives
with in vitro and in vivo antitumor effect on human leukemia
cell lines. Iwata et al.28 reported phenoxazine derivatives of
ability to suppress proliferation of poliovirus and porcine
parvovirus. Idries and Abeed29 synthesized 10H-substituted
INTRODUCTION
Phenoxazinones are coplanar, tricyclic compounds con-
taining two or even more additional functional groups (R)
from amino-, oxygen-, benzene-, sulfonic-, methyl-, ethyl- and
hydroxyl-substituents1. The phenoxazinone core (1) has been
found in various biological systems including pigments
produced by diverse organisms such as insects2, fungi3 and
Australian marsupials4. It seems to participate in a mechanism
to protect mammalian tissue from oxidative damage5 and forms
the core structure of certain antibiotics. It is also considered to
contribute to the activity of phenoxazinone antibiotics, allowing
the compounds to intercalate nucleic acids, in which so many
phenoxazinones are effective anticancer agents6. The core
structure is also found in the dyes resazurin (2) and resorufin
(3)7 and some phenoxazinone compounds are used as substrate
probes for the detection of enzymes8 and the amplification of
the antibiotic activity of other antibiotics9. Phenoxazinones
have also been detected as by-products in the growth medium
of Pseudomonas putida strain TW3, when the strain was grown
on 4-nitro-substituted substrates10. It is therefore not surprising
that various enzymes have been reported to be involved in the
production of the core structure. One example from nature is
3-hydroxyanthranilic acid (3-HAA) (4), which is the precursor
of the laccase-catalyzed formation of the phenoxazinone
derivative cinnabarinic acid (5) in the fungus Pycnoporus
cinnabarinus6,11. Dactinomycin also known generically as

3070 Odaa et al.
Asian J. Chem.
phenoxazine-3-yl-6-pyrimidin-2-phenylthiol/ol/amine/thiol
pyrroles using 2-[4-hydroxybenz-1(propene-1-one)]pyrrole.
Frade et al.30 reported benzo[a]phenoxazine heterocycles with
antimicrobial activity. Persson31 reported the synthesis of non-
conjugate potential-stepping phenothiazine and phenoxazine
based polymer hole-transport material for dye-sensitized solar
cells. Kohli et al.32 reported 5-(2-aryl-4-oxo-1,3-thiazolidine)-
2-(phenoxa-zinylmethyl)-1,3,4-thiadiazole derivatives with
anti-tubercular activity. Pereira et al.33 reported benzo[a]pheno-
xazinium chlorides used in Candida albicans inactivation by
photodynamic therapy. Quite a number of researchers have
reported varieties of methodologies for the synthesis of pheno-
xazinone. Gomes et al.34 reported the synthesis of pitucamycin,
a structural merger of a phenoxazinone with an epoxyquinone
antibiotics. Tomoda et al.35 reported the conversion of 2-amino-
5-methylphenol to the dihydrophenoxazinone derivatives with
reddish brown colour using purified human hemoglobin,
lysates of human erythrocytes or human erythrocytes. Hassanein
et al.36 repoted the synthesis of phenoxazinones via cobalt(I)
phthalocyanine tetrasodium sulfonate catalyzed molecular
oxygen oxidation of 2-aminophenol. Kaizer et al.37 reported
the synthesis of 2-aminophenoxazin-3-one using 2,2,6,6-tetra-
methyl-1-piperidinyloxyl (TEMPO) initiated oxidation of
2-aminophenol. Forte et al.38 reported the synthesis of novel
phenoxazinone dye using luccase action on 3-amino-4-
hydroxybenzenesulphonic acid. Maurya et al.39 reported the
biomimetic oxidative coupling of 2-aminophenol to 2-amino-
phenoxazin-3-one using bis(2-[α-hydroxyethyl]benzimida-
zolato) copper(II) anchored onto chloromethylated poly-
styrene. Hayakawa et al.40 reported the successful oxidation
of benzo[a]phenoxazine with ethanolic ferric chloride to obtain
benzo[a]phenoxazin-5-one, indicating that the position 5 is
the center which is most susceptible to oxidization. Hayakawa
et al.40 prepared 1-substituted-6-halogenobenzo[a]-11-azaphe-
noxazin-5-one and 4-substituted-6-halogeno-benzo[a]-11-
azaphenoxazin-5-one by simple condensation of 2-amino-3-
hydroxypyridine with 2,3-dihalogeno-1,4-naphthoquinone in
ethanolic-benzene in the presence of anhydrous potassium
acetate. In view of the interesting pharmacological applications
of this class of compound we report in this work the palladium
catalyzed synthesis of angular diazaphenoxazinone via
Buchwald-Hartwig amidation reaction.
Research Institute for Chemical Technology, Zaria) using
matched 1 cm quartz cells. The absorption maxima were given
in nanometer (nm). Fourier Transform Infrared spectral data
were recorded on FTIR 8400S using KBr disc. Nuclear magnetic
resonance (1H NMR and 13C NMR) was determined using
Varian NMR Mercury-200BB Spectrophotometer (Obafemi
Awolowo University, Ile-Ife). Chemical shifts were reported
in δ(neat).Analytical samples were obtained by column chroma-
tography on silica gel (Merck 70-325 meshASTM) by emplo-
ying methanol and acetone (2:1) as eluent followed by recrysta-
llization. The elemental analysis was done on a Heraeus CHN-
O rapid analyzer. The molecular masses of the compounds
were determined by GCMS-QP2010 PLUS SCHIMADZU,
Japan. All the reagents were of analytical grade and purchased
from Sigma-Aldriech Germany and used without further
purification.
11-Amino-6-chloro-8,10-diazabenzo[a]phenoxazin-5-
one(9): 4,5-Diamino-6-hydroxypyrimidine (0.56 g), sodium
acetate (0.36 g) and benzene (60 mL) mixed with dimethyl
formamide (30 mL) were charged into 250 mL two-necked
round bottomed flask fitted with short magnetic stirring bar and
a reflux condenser. The mixture was stirred while heating on a
water bath at 70-75 °C for 45 min. Thereafter, 2,3-dichloro-
1,4-naphthoquinone (1 g) was added and the stirring continued
with heating at 70-75 °C for 8 h. The colour of the reaction
mixture changed from light brownish green to yellow red and
intense red as the reaction progressed. At the end of the 8 h,
the reaction mixture was filtered and cooled in ice overnight
and filtered again to give the solid compound.Analytical sample
was obtained by column chromatography using benzene as
the eluting solvent followed by recrystallization to obtain the
target compound;Yield 4.80 g, (55 %); m.p. 293 °C; the litera-
ture melting point (290 °C), UV-visible (benzene) λmax: 465 nm.
IR (KBr, νmax, cm-1): 3500 and 3350 (NH2), 2932 (Ar-H), 1678
(C=O), 1350 (aromatic C-N), 1265 (C-O-C), 733 (C-Cl). 1H
NMR (CDCl3): δ8.3 (m, 4H,Ar-H), 7.9 (s, 1H,Ar-H). 13C NMR
(CDCl3): δ 170.20, 142.81, 139.85, 135.45, 134.09, 132.10,
131.32, 130.29, 128.50, 125.27, 123.38, 117.86, 110.20.
Reduction of 11-amino-6-chloro-8, 10-diazabenzo[a]-
phenoxazin-5-one (10): 11-Amino-8,11-diazabenzo[a]pheno-
xazin-5-one (0.56 g, 0.0044 mol), sodium dithionite (2 g, 0.0044
mol), acetone (25 mL) and 2 drops of DMSO were put in 100 mL
two necked round bottom flask and refluxed for 0.5 h. Water
(5 mL) was added and the reddish colour changed immediately
to light yellow and subsequently colourless. This colourless
solution then changed back to red on exposure to air. The
product precipitated with water, isolated and found to be 11-
amino-6-chloro-8,10-diazabenzo[a]-phenoxazin-5-one by
instrumental analysis.
O
N
N
N
NaO
R
O
O
O
O
NaO
R1
O
O
1
3
2
R
COOH
O
O
R2
NH2
OH
N
NH2
O
N
O
NH2
O
Procedure for amide synthesis: This preparation was
carried out in a fume cupboard. Carboxylic acids (10 g) were
heated with 30 g (excess) of thionyl chloride on a boiling water
bath for 3 min. under reflux. Thereafter the mixture was heated
for further 10 min. The solution was gradually cooled to 0 °C
and 150 mL of concentrated ammonia was added in drops.
The product was filtered and recrystallized from water. The
amides prepared include salicylamide (m.p. 144-145 °C), the
literature (m.p. 140-144 °C), yield (4.40 g, 44 %), UV-visible
(methanol) λmax: 298.4 nm; benzamide (m.p. 129-130 °C), the
4
O
5
CH3
CH3
6
EXPERIMENTAL
Melting points of the compounds were determined using
electro-thermal melting point apparatus in open capillaries and
are uncorrected. Ultra violet and visible spectra were recorded
on a UNICO-UV 2500PC series spectrophotometer at (National

Vol. 27, No. 8 (2015)
Synthesis of Novel Angular Diazaphenoxazinone Derivatives 3071
literature (m.p. 128-129 °C), yield (6.10 g, 61 %), UV-visible
(methanol) λmax: 287 nm and 4-nitrobenzamide (m.p. 248-249
°C), the literature (m.p. 245-248 °C), yield (5.10 g, 51 %),
UV-visible (methanol) λmax: 357.4 nm.
the crude product which was recrystallized from acetone and
methanol (1:2) to give 11-amino-6-(2-hydroxybenzamido)-
8,10-diazabenzo[a]phenoxazin-5-one as a reddish solid.Yield
14.71 %, m.p 310 °C, m.w. 399.35. Elemental analysis of
C21H13N5O4 (calcd.): C 63.16, H 3.28, N 17.54; found: C 63.20,
H 3.31, N 17.48. UV-visible (acetone, λmax): 480.5 nm. FTIR
(KBr, νmax, cm-1): 3377, 3200 (NH2), 3180 (b, OH), 3000 (Ar-
11-Amino-6-acetamido-8,10-diazabenzo[a]phenoxazin-
5-one (13a):This compound was prepared by heating palladium
acetate (67 mg, 0.015 mmol), water (0.06 mmol) and triphenyl-
phosphine (0.045 mmol) for 1.5 min at 110 °C in t-butanol to
give a highly active catalyst Pd(0). Thereafter, potassium
phosphate (180 mg, 1 mol), acetamide (49 mg, 1 mol) and 11-
amino-6-chloro-8,10-diazabenzo[a]-pheno-xazin-5-one (250
mg, 1 mol) were added and refluxed for 3 h to give orange red
solution. The solution was filtered and the filtrate allowed to
evaporate to dryness and the residue recrystallized with a
mixture of methanol and acetone (2:1) to obtain 11-amino-6-
ethanamido-8,10-diazabenzo[a]phenoxazin-5-one as a brick
red solid. Yield 1.8 g (16.83 %), m.p. 320 °C, m.w. 321.29.
Elemental analysis of C16H11N5O3 (calcd.): C 59.81, H 3.45, N
21.80; found: C 59.72, H 3.50, N 21.72. UV-visible (acetone,
1
H), 1690, 1641 (C=O), 1570 (C=C), 1150 (C-O). H NMR
(DMSO): δ 8.1 (m, 4H, Ar-H), 7.5 (m, 4H, Ar-H). 13C NMR
(DMSO): δ 170.03, 168.358, 153.34, 152.90, 149.08, 148.37,
143.21, 140.27, 136.45, 135.94, 134.69, 133.86, 131.07,
131.66, 130.45, 128.85, 127.89, 125.63, 120.34, 117.32,
110.65.
11-Amino-6-(4-nitrobenzamido)-8,10-diazabenzo[a]-
phenoxazin-5-one (13d): This compound was prepared by
heating palladium acetate (67 mg, 0.015 mmol), water (0.06
mmol) and triphenylphosphine (89 mg, 0.045 mmol) for 1.5
min at 110 °C in t-butanol to give a highly active catalyst Pd(0)
as a greenish-light yellow solution. Potassium phosphate (180
mg, 1 mol), 4-nitrobenzamide (138 mg, 1 mol) and 11-amino-
6-chloro-8,10-diazabenzo[a]phenoxazin-5-one (250 mg,
1 mol) were added to the solution and refluxed for 3 h at 110 °C
to give a reddish solution. The solution was filtered and the
solvent evaporated using rotary evaporator. The product was
recrystallized from a mixture of acetone and methanol (1:2)
to obtain 11-amino-6-(4-nitrobenzamido)-8,10-diazabenzo[a]-
phenoxazinone as an orange red solid. Yield 13.17 %, m.p.
330-331 °C, m.w. 428.35. Elemental analysis of C21H12N6O5
(calcd.): C 58.88, H 2.82, N 19.62; found: C 58.57, H 2.90, N
λ
max): 482 nm, FTIR (KBr, νmax, cm-1): 3452, 3200 (NH2), 3057
(Ar-H), 1685, 1679 (2C=O), 1432 (aromatic C-N), 1264(C-
O), 734 (substitution in benzene). 1H NMR (DMSO): δ 7.78
(m, 4H, Ar-H), 1.85 (s, 3H, CH3). 13C NMR (DMSO): δ 169,
160, 154, 152, 148, 142, 137, 135, 134, 131, 128, 125.88,
125.65, 120, 111, 41.
11-Amino-6-benzamido-8,10-diazabenzo[a]phenoxa-
zin-5-one (13b):A mixture of palladium acetate (67 mg, 0.015
mmol), water (0.06 mmol) and triphenylphosphine (89 mg,
0.045 mmol) were heated for 1.5 min at 110 °C in t-butanol to
give a highly active catalyst Pd(0) in a greenish-light yellow
solution. Thereafter, potassium phosphate (180 mg, 1 mol),
benzamide (41 mg, 1 mol) and 11-amino-6-chloro-8,10-diaza-
benzo[a]phenoxazin-5-one (250 mg, 1 mol) were added and
refluxed for 3 h at 110 °C to give a reddish solution. The solution
was filtered and the filtrate allowed to evaporate to dryness,
the product was recrystallized from a mixture of acetone and
methanol (1:2) to obtain 11-amino-6-benzamido-8,10-diaza-
benzo[a]phenoxazin-5-one as a brick red solid. Yield (11 %),
m.p. > 300 °C, m.w. 383.35. Elemental analysis of C21H13N5O3
(calcd.): C 5.79, H 3.42, N 18.29; found: C 65.80, H 3.40, N
20.03. UV-visible (acetone λmax): 480 nm. FTIR (KBr, νmax
,
cm-1): 3500, 3460 (NH2), 3056, 3000 (Ar-H), 1680, 1659
(2C=O), 1600 (C=C), 1550 (C=N), 1263 (C-O), 734 (substitu-
tion in benzene ring). 1H NMR (DMSO): δ 8.4 (m, 4H, Ar-H),
7.5 (m, 4H, Ar-H). 13C NMR (DMSO): δ 170.51, 168.73,
153.35, 151.56, 149.90, 148.20, 147.78, 139.98, 138.98, 138.60,
137.85, 137.02, 135.91, 135.12, 132.22, 131.01, 130.90, 126.99,
124.06, 123.55, 119.20.
RESULTS AND DISCUSSION
The reaction of 4,5-diamino-6-hydroxypyrimidine (7) and
2,3-dichloro-1,4-naphthoquinone (8) afforded the key
intermediate 11-amino-6-chloro-8,10-diazabenzo[a]phenoxa-
zinone (9) (Scheme-I). The benzamides (12a-c) was synthe-
sized by the simultaneous reaction of benzoic acids (11a-c),
thionyl chloride and concentrated ammonia (Scheme-II). The
palladium catalyzed Buchwald-Hartwig reaction of 11-amino-
6-chloro-8,10-diazabenzo[a]phenoxazinone (9) and amides
(acetamide and benzamides 12a-c) afforded the amide deriva-
tives of angular diazaphenoxazinone (13a-d) (Scheme-III).
The UV results revealed an increased wavelength of maximum
absorption which is implicated by the increased conjugation
in the amide derivatives when compared with the intermediate.
Although not much change is expected from the FTIR, the
presence of two carbonyl bands in the amide derivatives is
diagnostic. The two carbonyl peaks observed in the carbon-13
NMR and the elemental analysis further proved the successful
synthesis of the angular diazaphenoxazinone derivatives
reported.
18.45. UV-visible (acetone, λmax): 468 nm. FTIR (KBr, νmax
,
cm-1): 3360, 3171 (NH2), 1680, 1644 (C=O), 1397 (aromatic
C-N), 1125 (C-O), 775 (substitution in benzene ring). 1H NMR
(CDCl3): δ 7.9 (m, 5H, Ar-H), 7.5 (m, 4H, Ar-H), 7.4 (s, 1H,
Ar-H), 6.4 (s, 1H, NH), 2.5 (s, 2H, NH2). 13C NMR (CDCl3): δ
171, 170, 152, 148, 145, 142, 140.25, 139.30, 138.04, 137.97,
137.20, 134.56, 132.98, 132.25, 131.08, 130.28, 129.39,
128.60, 127.09, 126.90, 118.89.
11-Amino-6-(2-hydroxybenzamido)-8,10-diazabenzo-
[a]phenoxazin-5-one (13c): This compound was obtained by
heating palladium acetate (68 mg, 0.015 mmol), water (0.06
mmol) and triphenylphosphine (89 mg, 0.045 mmol) for 1.5
min at 110 °C in t-butanol to give a highly active catalyst Pd(0).
Potassium phosphate (180 mg, 1 mol), salicylamide (117 mg,
1 mol) and 11-amino-6-chloro-8,10-diaza-benzo[a]pheno-
xazin-5-one (250 mg, 1 mol) were added to the pre-activated
catalyst and refluxed for 3 h at 110 °C to give a reddish solution.
The solution was filtered and the solvent evaporated to obtain

3072 Odaa et al.
Asian J. Chem.
o
NH
O
O
NH
2
2
i. SOCl , 100 C, 13 min
2
Cl
Cl
N
O
NH
2
RCONH
N
N
AcNa, DMF/C H
6
RCOOH
6
2
+
o
12a-c
ii. 0 C, NH
N
O
11a-c
N
OH
3
9
7
Cl
Scheme-II: Preparation of amides
8
NH
2
NH
N
2
Na S O /DMSO,
H O, heat
2
N
O
2 2 2
The acids include benzoic acid, 2-hydroxybenzoic acid
and 4-nitrobenzoic acid to generate benzamide, 2-hydroxy-
benzamide and 4-nitrobenzamide, respectively. The acetamide
was sourced commercially.
N
N
N
air
N
O
O
OH
Cl
9
10
Cl
Scheme-I:Synthesis of 11-amino-6-chloro-8,10-diazabenzo[a]phenoxazin-
5-one
NH2
NH2
1 mole% Pd(OAc)2, 3 mole% PPh3
4 mole% H2O, K3PO4, t-BuOH
N
N
N
N
RCONH2, 110oC, 3 h
12a-c
O
R
N
O
O
N
O
NH
Cl
9
13a-d
O
NH2
N
N
O
O
N
O
NH
13d
O
NO2
NH2
O
O2N
NH2
12c
NH2
NH2
N
N
NH2
N
N
CH3CONH2
OH
N
12b
N
O
O
N
O
N
O
O
O
NH
CH3
NH
O
N
O
13a
9
Cl
O
OH
NH2
13c
12a
NH2
N
N
O
O
N
O
NH
13b
Scheme-III: Synthesis of 11-amino-6-amido-8,10-diazabenzo[a]phenoxazin-5-ones

Vol. 27, No. 8 (2015)
Synthesis of Novel Angular Diazaphenoxazinone Derivatives 3073
18. A. Iwata, T. Yamaguchi, K. Sato, R. Izumi and A. Tomoda, Tohoku J.
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Conclusion
The synthesis of 11-amino-6-chloro-8,10-diazabenzo[a]-
phenoxazinone (9) and its transformation to the various substi-
tuted amide derivatives (13a-d) via Buchwald-Hartwig tandem
amidation protocol has been achieved successfully. The struc-
tural assignments were supported by ultraviolet/visible, Fourier
transform infrared, 1H NMR and 13C NMR spectroscopy and
elemental analysis.
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