(N-Isocyanimino)triphenylphosphorane-mediated, one-pot, efficient synthesis of sterically congested 1,1,1-trifluoro-2-(5-aryl-1,3,4-oxadiazol-2-yl)-2- propanol derivatives via intramolecular Aza-Wittig Reaction

Article abstract of DOI:10.1080/10426501003713098

Reactions of (N-isocyanimino)triphenylphosphorane with 1,1,1- trifluoroacetone in the presence of aromatic (or heteroaromatic) carboxylic acids (3-methylbenzoic acid, 1-naphthalenecarboxylic acid, 2- naphthalenecarboxylic acid, 2-furancarboxylic acid, and

Full text of DOI:10.1080/10426501003713098

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(N-Isocyanimino)triphenylphosphorane-
Mediated, One-Pot, Efficient Synthesis of
Sterically Congested 1,1,1-Trifluoro-2-
(5-aryl-1,3,4-oxadiazol-2-yl)-2-propanol
Derivatives via Intramolecular Aza-Wittig
Reaction
Ali Ramazani a , Nahid Shajari a , Amir Tofangchi Mahyari a , Mehdi
Khoobi a , Yavar Ahmadi b & Ali Souldozi c
a Chemistry Department , Zanjan University , Zanjan, Iran
b Member of Young Researchers Club , Islamic Azad University ,
Zanjan Branch, Zanjan, Iran
c Chemistry Department , Islamic Azad University–Urmia Branch ,
Urmia, Iran
Published online: 19 Nov 2010.
To cite this article: Ali Ramazani , Nahid Shajari , Amir Tofangchi Mahyari , Mehdi Khoobi , Yavar
Ahmadi & Ali Souldozi (2010) (N-Isocyanimino)triphenylphosphorane-Mediated, One-Pot, Efficient
Synthesis of Sterically Congested 1,1,1-Trifluoro-2-(5-aryl-1,3,4-oxadiazol-2-yl)-2-propanol Derivatives
via Intramolecular Aza-Wittig Reaction, Phosphorus, Sulfur, and Silicon and the Related Elements,
185:12, 2496-2502, DOI: 10.1080/10426501003713098
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Phosphorus, Sulfur, and Silicon, 185:2496–2502, 2010
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426501003713098
(N-ISOCYANIMINO)TRIPHENYLPHOSPHORANE-
MEDIATED, ONE-POT, EFFICIENT SYNTHESIS OF
STERICALLY CONGESTED 1,1,1-TRIFLUORO-2-(5-ARYL-
1,3,4-OXADIAZOL-2-YL)-2-PROPANOL DERIVATIVES VIA
INTRAMOLECULAR AZA-WITTIG REACTION
Ali Ramazani,1 Nahid Shajari,1 Amir Tofangchi Mahyari,1
Mehdi Khoobi,1 Yavar Ahmadi,2 and Ali Souldozi3
1Chemistry Department, Zanjan University, Zanjan, Iran
2Member of Young Researchers Club, Islamic Azad University, Zanjan Branch,
Zanjan, Iran
3Chemistry Department, Islamic Azad University–Urmia Branch, Urmia, Iran
Reactions of (N-isocyanimino)triphenylphosphorane with 1,1,1-trifluoroacetone in
the presence of aromatic (or heteroaromatic) carboxylic acids (3-methylbenzoic acid,
1-naphthalenecarboxylic acid, 2-naphthalenecarboxylic acid, 2-furancarboxylic acid,
and 2-thiophenecarboxylic acid) proceed smoothly at room temperature and in neutral
conditions to afford sterically congested 1,1,1-trifluoro-2-(5-aryl-1,3,4-oxadiazol-2-yl)-2-
propanol derivatives in high yields. The reaction proceeds smoothly and cleanly under mild
conditions, and no side reactions were observed.
Supplemental materials are available for this article. Go to the publisher’s online edition of
Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental
file.
Keywords Aromatic carboxylic acid; aza-Wittig reaction; heteroaromatic carboxylic acid;
(N-isocyanimino)triphenylphosphorane; 1,3,4-oxadiazole; 1,1,1-trifluoroacetone
INTRODUCTION
Organophosphorus compounds1–5 have been extensively employed in organic syn-
thesis as useful reagents, as well as ligands, in a number of transition metal catalysts.3
Iminophosphoranes are a class of special type of zwitterions that bear a strongly nu-
cleophilic, electron-rich nitrogen. The electron distribution around the P+–N− bond and
its consequent chemical implications have been probed and assessed through theoretical,
spectroscopic, and crystallographic investigations.6 The proton affinity of these iminophos-
phoranes can be used as a molecular guide to assess their utility as synthetic reagents and
their function as ligands in coordination and organometallic chemistry.6–14
Received 15 January 2010; accepted 18 February 2010.
This research was supported by the Zanjan University and the Iran National Science Foundation (INSF).
Address correspondence to Ali Ramazani, Chemistry Department, Zanjan University, PO Box 45195-313,
Zanjan, Iran. E-mail: aliramazani@gmail.com
2496

(N-ISOCYANIMINO)TRIPHENYLPHOSPHORANE-MEDIATED SYNTHESIS
2497
The intramolecular version of the aza-Wittig–type reaction has attracted consider-
able attention recently because of its high potential for the synthesis of a wide variety
of nitrogen heterocycles, which can be attributed, in good measure, to the rapid progress
in the preparation of functionalized iminophosphoranes. Several interesting heterocycliza-
tion reactions involving iminophosphoranes have been reviewed.6–12 These compounds can
easily be converted through the aza-Wittig reaction with isocyanates, carbon dioxide, or
carbon disulfide into functionalized heterocumulenes, which exhibit a rich chemistry of
unusual synthetic promise.6–12 The nucleophilicity at the nitrogen is a factor of essential
mechanistic importance in the use of these iminophosphoranes as aza-Wittig reagents.
Iminophosphoranes are important reagents in synthetic organic chemistry, especially in the
synthesis of naturally occurring products and compounds with biological and pharmacolog-
ical activity.6–12 However, the organic chemistry of (N-isocyanimino)triphenylphosphorane
3 remains almost unexplored.13,14 (N-Isocyanimino)triphenylphosphorane 3 is expected to
have synthetic potential because it provides a reaction system in which the iminophos-
phorane group can react with a reagent having a carbonyl functionality.13,14 In recent
years, we have established a one-pot method for the synthesis of organophosphorus
compounds.15–24 As part of our ongoing program to develop efficient and robust meth-
ods for the preparation of heterocyclic compounds,25–32 we sought to develop a conve-
nient preparation of 1,1,1-trifluoro-2-(5-aryl-1,3,4-oxadiazol-2-yl)-2-propanols 4a–f from
(N-isocyanimino)triphenylphosphorane 3, 1,1,1-trifluoroacetone 2, and aromatic (or het-
eroaromatic) carboxylic acids 1 (3-methylbezoic acid, 1-naphthalenecarboxylic acid, 2-
naphthalenecarboxylic acid, 2-furancarboxylic acid, and 2-thiophenecarboxylic acid) in
excellent yields under neutral conditions (Scheme 1).
O
_
CH2Cl2
r.t., 4 h
F3C
HO
N
O
+
N
Ph3PO
C
N
N
ArCO2H
+
+
+
Me
CF3
PPh3
5
Me
3
1
2
Ar
4
Scheme 1 Three-component synthesis of sterically congested 2,5-disubstituted 1,3,4-oxadiazoles 4 (see Table I).
1,3,4-Oxadiazoles have attracted interest in medicinal chemistry as surrogates of
carboxylic acids, esters, and carboxamides. They are an important class of heterocyclic
compounds that have a wide range of pharmaceutical and biological activities including
antimicrobial, antifungal, anti-inflammatory, and antihypertensive.33–39 Several methods
have been reported in the literature for the synthesis of 1,3,4-oxadiazoles. These protocols
are multistep in nature.40–45 The most general method involves the cyclization of diacylhy-
drazides with a variety of reagents, such as thionyl chloride, phosphorous oxychloride, or
sulfuric acid, usually under harsh reaction conditions. Few reliable and operationally sim-
ple examples have been reported for the one-step synthesis of 1,3,4-oxadiazoles, especially
from readily available carboxylic acids and acid hydrazides.46–50
RESULTS AND DISCUSSION
In the last years, several synthetic methods have been reported for the prepara-
tion of (N-isocyanimino)triphenylphosphorane (CNNPPh3) 3 (Scheme 1).13,14 There are

2498
A. RAMAZANI ET AL.
Table I Synthesis of sterically congested 2,5-disubstituted 1,3,4-oxadiazoles derivatives 4 (see Scheme 1)
4
Ar
Yield%)a,b
a
b
c
d
e
f
3-MeC6H4
1-Naphthyl
2-Naphthyl
2-Furyl
2-Thienyl
2-BrC6H4
88
86
83
87
80
82
aWe also used acetone and acetophenone instead of 1,1,1-trifluoroacetone 2 in this reaction, but no correspond-
ing products 4 were observed.
bIsolated yields.
several reports for the use of (N-isocyanimino)triphenylphosphorane 3 in the synthe-
sis of metal complexes.13,14 However, the application of 3 in the synthesis of organic
compounds is rare.25–31 As part of our ongoing program to develop efficient and ro-
bust methods for the preparation of heterocyclic compounds,25–32 we sought to develop
a convenient preparation of sterically congested 2,5-disubstituted 1,3,4-oxadiazoles 4 from
(N-isocyanimino)triphenylphosphorane 3, 1,1,1-trifluoroacetone 2, and aromatic (or het-
eroaromatic) carboxylic acids 1 (3-methylbenzoic acid, 1-naphthalenecarboxylic acid, 2-
naphthalenecarboxylic acid, 2-furancarboxylic acid, and 2-thiophenecarboxylic acid) in
excellent yields under neutral conditions (Scheme 1). The carboxylic acid derivative 1 with
1,1,1-trifluoroacetone 2 and (N- isocyanimino)triphenylphosphorane 3 in CH2Cl2 react to-
gether in a 1:1:1 ratio at room temperature to produce sterically congested 2,5-disubstituted
1,3,4-oxadiazoles 4 and triphenylphosphine oxide 5 (Scheme 1 and Table I). The reac-
tion proceeds smoothly and cleanly under mild conditions, and no side reactions were
observed. We also used acetone and acetophenone instead of 1,1,1-trifluoroacetone 2 in
this reaction, but no corresponding products 4 were observed. In the both cases, 2-aryl-
1,3,4-oxadiazoles and triphenylphosphine oxide 5 were observed, as has been previously
reported,26 and the acetone and acetophenone were recovered unreacted at the end of reac-
tion. As indicated in Table I, the reactions proceeded efficiently with an electron-poor ketone
(1,1,1-trifluoroacetone) 2, and electron-rich ketones such as acetone and acetophenone are
not suitable starting materials in these reactions.
3
The structures of the products were deduced from their IR, mass, H NMR, and C
NMR spectra. The mass spectra of these compounds displayed molecular ion peaks at the
appropriate m/z values. The H NMR spectrum of 4a consisted of two singlets for the 2 CH3
(δ = 1.93 and 2.43), a broad singlet for a OH (δ = 4.95–5.50, exchangeable by D2O), and two
multiplets for the aromatic protons [δ = 7.18–7.61 (m, 2H, arom) and δ = 7.63–8.02 (m, 2H,
arom)]. The 1H decoupled 13C NMR spectrum of 4a showed 12 distinct resonances, partial
assignment of these resonances is given in the Experimental section. The 1H and 13C NMR
spectra of compounds 4b–f were similar to those of 4a, except for the aromatic or heteroaro-
matic moieties, which exhibited characteristic signals with appropriate chemical shifts.
A mechanistic rationalization for this reaction is provided in Scheme 2. On the
basis of the chemistry of isocyanides,19–25 it is reasonable to assume that the first step
may involve nucleophilic addition of the (N-isocyanimino)triphenylphosphorane 3 to the
1,1,1-trifluoroacetone 2, which facilitates by its protonation with the acid 1, leading to
nitrilium intermediate 6. This intermediate may be attacked by conjugate base of the acid
7 to form 1:1:1 adduct 8. This adduct may undergo intramolecular aza-Wittig25–29 reaction

(N-ISOCYANIMINO)TRIPHENYLPHOSPHORANE-MEDIATED SYNTHESIS
2499
O
CF3
OH
F3C
+
N
HO
Ar
_
+
N
N
C
O
N
N
C
Ph3P
O
2
1
Ph3P
6
3
_
O
Ar
7
Ph3P
O
+
Ph3P
_
CF3
N
O
F3C
HO
N
O
N
N
CF3
N
+
Ph3PO
O
OH
Ar
O
Ar
OH
Ar
5
9
4
8
Scheme 2 The proposed mechanism for the formation of sterically congested 2,5-disubstituted 1,3,4-oxadiazole
derivatives 4.
of the iminophosphorane moiety with the ester carbonyl to afford the isolated sterically
congested 2,5-disubstituted 1,3,4-oxadiazoles 4 by removal of triphenylphosphine oxide 5
from intermediate 9.
We believe that the reported method offers a mild, simple, and efficient route for the
preparation of sterically congested 2,5-disubstituted 1,3,4-oxadiazole derivatives. Its ease
of workup, high yields, and fairly mild reaction conditions make it a useful addition to
modern synthetic methodologies. Other aspects of this process are under investigation.
EXPERIMENTAL
Starting materials and solvents were obtained from Merck (Germany) and Fluka
(Switzerland) and were used without further purification. The methods used to follow the
reactions were TLC and NMR. TLC and NMR indicated that there is no side product.
Melting points were measured on an Electrothermal 9100 apparatus and are uncorrected.
1
IR spectra were measured on a Jasco 6300 FTIR spectrometer. H and 13C NMR spectra
were measured (CDCl3 solution) with a Bruker DRX-250 Avance spectrometer at 250.0
and 62.5 MHz, respectively. Elemental analyses were performed using a Heraeus CHN-O-
Rapid analyzer. Mass spectra were recorded on a Finnigan-MATT 8430 mass spectrometer
operating at an ionization potential of 20 eV. Flash chromatography columns were prepared
from Merck silica gel powder.
General Procedure for the Preparation of Compounds 4a–f (Exemplified
for 4a)
To a magnetically stirred solution of (N-isocyanimino)triphenylphosphorane 3 (1
mmol) and 1,1,1-trifluoroacetone 2 (1 mmol) in CH2Cl2 (7 mL), a solution of 3-
methylbenzoic acid 1a (1 mmol) in CH2Cl2 (5 mL) was added dropwise at room tem-
perature over 15 min. The mixture was stirred for 4 h. The solvent was removed under
reduced pressure, and the viscous residue was purified by flash column chromatography
[silica gel powder: petroleum ether–ethyl acetate (2:1)]. The solvent was removed un-
der reduced pressure, and the products were obtained. The characterization data of the
compounds are given below:

2500
A. RAMAZANI ET AL.
1,1,1-Trifluoro-2-[5-(3-methylphenyl)-1,3,4-oxadiazol-2-yl]-2-propanol
(4a)
Yellow crystals; mp: 60.1–61.6◦C; Yield: 88%. IR (KBr) (vmax, cm−1): 3292 (br),
1692, 1560, 1162, 1088, 724. 1H NMR (CDCl3, 250 MHz): δH 1.93 and 2.42 (2 s, 6 H, 2
CH3), 4.95–5.50 (br. s, 1 H, OH; exchanged by D2O addition), 7.18–7.61 (m, 2 H, arom),
7.63–8.02 (m, 2 H, arom). 13C NMR (CDCl3, 62.5 MHz): δC 21.19 and 22.27 (2 CH3),
72.93 (q, 2Jcf = 32.1 Hz, C-CF3), 123.65 and 139.23 (2 C, arom), 124.64 (q, 1Jcf = 286.2
Hz, CF3), 125.34, 128.63, 130.07 and 134.32 (4 CH, arom), 164.99 and 167.54 (2 C N).
Anal. Calcd for C12H11F3N2O2 (272.2): C, 52.94; H, 4.07; N, 10.29%. Found: C, 52.99; H,
4.04; N, 10.32. MS (EI): m/z (%) = 272 (M+, 48), 203 (48), 161 (48), 159 (50), 136 (32),
119 (50), 91 (100), 77 (11), 65 (21) and 43 (28).
1,1,1-Trifluoro-2-[5-(1-naphthyl)-1,3,4-oxadiazol-2-yl]-2-propanol (4b)
White crystals; mp: 149.2–151.0◦C; Yield: 86%. IR (KBr) (vmax, cm−1): 3472 (br),
1540, 1165, 1103, 772. 1H NMR (CDCl3, 250 MHz): δH 1.99 (s, 3 H, CH3), 4.17 (s, 1 H,
OH), 7.52–7.78 (m, 3 H, arom), 7.95 (d, 3Jhh = 8.0 Hz, 1 H, arom), 8.08 (d, 3Jhh = 8.0 Hz,
1 H, arom), 8.18 (d, 3Jhh = 7.2 Hz, 1 H, arom), 9.13 (d, 3Jhh = 8.5 Hz, 1 H, arom).13C NMR
2
(CDCl3, 62.5 MHz): δC 20.46 (CH3), 72.38 (q, Jcf = 32.1 Hz, C-CF3), 119.89, 130.32
and 134.16 (3 C,arom), 124.01 (q, 1Jcf = 286.2 Hz, CF3), 125.16, 126.15, 127.26, 128.83,
129.14, 129.27 and 133.69 (7 CH, arom), 163.63 and 166.87 (2 C N). Anal. Calcd for
C15H11F3N2O2 (308.2): C, 58.45; H, 3.60; N, 9.09%. Found: C, 58.41; H, 3.62; N, 9.03.
MS (EI): m/z (%) = 308 (M+, 22), 239 (4), 197 (14), 155 (50), 153 (100), 126 (75), 76
(16), 63 (18) and 43 (62).
1,1,1-Trifluoro-2-[5-(2-naphthyl)-1,3,4-oxadiazol-2-yl]-2-propanol (4c)
Yellow crystals; mp: 138.5–140.2◦C; Yield: 83%. IR (KBr) (vmax, cm−1): 3274 (br),
1
1556, 1155, 1096, 763. H NMR (CDCl3, 250 MHz): δH 1.99 (s, 3 H, CH3), 4.94–5.18
(br. s, 1 H, OH; exchanged by D2O addition), 7.47–7.67 (m, 2 H, arom), 7.74–7.97 (m,
3
3 H, arom), 8.07 (d, Jhh = 8.7 Hz, 1 H, arom), 8.52 (s, 1 H, arom). 13C NMR (CDCl3,
62.5 MHz): δC 21.27 (CH3), 72.99 (q, 2Jcf = 32.1 Hz, C-CF3), 120.99, 133.63 and 135.91
(3 C, arom), 123.96, 128.26, 128.96, 129.37, 129.90 and 130.19 (7 CH, arom), 124.69 (q,
1Jcf = 286.2 Hz, CF3), 165.04 and 167.61 (2 C N). Anal. Calcd for C15H11F3N2O2 (308.2):
C, 58.45; H, 3.60; N, 9.09%. Found: C, 58.51; H, 3.62; N, 9.05. MS (EI): m/z (%) = 308
(M+, 55), 239 (12), 197 (29), 155 (100), 153 (84), 127 (82), 100 (11), 77 (11), 63 (10) and
43 (39).
1,1,1-Trifluoro-2-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-2-propanol (4d)
Yellow crystals; mp: 120.7 (dec) ◦C; Yield: 87%. IR (KBr) (vmax, cm−1): 3245 (br),
1642, 1526, 1155, 1096, 751. 1H NMR (CDCl3, 250 MHz): δH 1.92 (s, 3 H, CH3), 4.51 (s,
1 H, OH; exchanged by D2O addition), 6.62 (s, 1 H, furan), 7.25 (s, 1 H, furan), 7.66 (s, 1
H, furan).13C NMR (CDCl3, 62.5 MHz): δC 20.39 (CH3), 72.27 (q, 2Jcf = 32.1 Hz, C-CF3),
1
112.71, 115.76 and 146.73 (3 CH, furan), 123.86 (q, Jcf = 286.2 Hz, CF3), 138.78 (C,
furan), 159.42 and 163.38 (2 C N). Anal. Calcd for C9H7F3N2O3 (248.2): C, 43.56; H,
2.84; N, 11.29%. Found: C, 43.62; H, 2.86; N, 11.24. MS (EI): m/z (%) = 248 (M+, 69),

(N-ISOCYANIMINO)TRIPHENYLPHOSPHORANE-MEDIATED SYNTHESIS
2501
194 (32), 179 (91), 137 (100), 108 (39), 95 (99), 52 (31) and 43 (69). Sample NMR, IR,
and mass spectra for 4d are shown in Figures S1–S6 (Supplemental Materials, available
online).
1,1,1-Trifluoro-2-[5-(2-thienyl)-1,3,4-oxadiazol-2-yl]-2-propanol (4e)
Yellow crystals; mp: 94.2–96.1◦C; Yield: 80%. IR (KBr) (vmax, cm−1): 3237 (br),
1603, 1163, 1108, 727. 1H NMR (CDCl3, 250 MHz): δH 1.92 (s, 3 H, CH3), 4.41–4.61 (br.
s, 1 H, OH; exchanged by D2O addition), 7.14–7.24 (m, 1 H, thiophene), 7.60 (d, 3Jhh
=
4.2 Hz, 1 H, thiophene), 7.81 (s, 1 H, thiophene).13C NMR (CDCl3, 62.5 MHz): δC 21.11
2
1
(CH3), 72.89 (q, Jcf = 32.1 Hz, C-CF3), 124.54 (q, Jcf = 286.2 Hz, CF3), 124.92 (C,
thiophene), 129.30, 131.88 and 132.20 (3 CH, thiophene), 163.61 and 164.17 (2 C N).
Anal. Calcd for C9H7F3N2O2S (264.2): C, 40.91; H, 2.67; N, 10.60%. Found: C, 40.99; H,
2.72; N, 10.56. MS (EI): m/z (%) = 264 (M+, 4), 195 (4), 153 (7), 124 (8), 111 (100), 96
(7), 82 (19), 69 (24) and 42 (32).
2-[5-(2-Bromophenyl)-1,3,4-oxadiazol-2-yl]-1,1,1-trifluoro-2-propanol
(4f)
◦
Yellow crystals; mp: 83.5–85.1 C; Yield: 82%. IR (KBr) (vmax, cm−1): 3431 (br),
1456, 1167, 1089, 728. 1H NMR (CDCl3, 250 MHz): δH 1.93 (s, 3 H, CH3), 4.08–4.32 (br.
s, 1 H, OH; exchanged by D2O addition), 7.35–8.02 (m, 4 H, arom). 13C NMR (CDCl3,
2
62.5 MHz): δC 20.36 (CH3), 72.36 (q, Jcf = 32.1 Hz, C-CF3), 122.15 and 124.76 (2 C,
arom), 123.90 (q, 1Jcf = 286.2 Hz, CF3), 128.06, 132.23, 133.48 and 134.97 (4 CH, arom),
164.62 and 165.78 (2 C N). Anal. Calcd for C11H8 BrF3N2O2 (337.1): C, 39.19; H, 2.39;
N, 8.31%. Found: C, 39.22; H, 2.44; N, 8.22. MS (EI): m/z (%) = 338 ([M++2], 8), 336
(M+, 7), 304 (6), 269 (10), 225 (31), 183 (58), 155 (29), 102 (22), 89 (36), 75 (100), 62
(35) and 43 (100).
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