Amidoalkylating properties of 1-(N -acylamino)alkyltriphenylphosphonium salts

Article abstract of DOI:10.1080/10426507.2012.744014

Easily accessible 1-(N-acylamino)alkyltriphenylphosphonium salts react smoothly with nitrogen, sulfur, phosphorus and oxygen nucleophiles in the presence of (i-Pr)₂EtN to give the expected α-amidoalkylation products, usually in good or very good yields. α-Amidoalkylation of dialkyl malonates or acetylacetates requires the application of a much stronger base (DBU) and gives the best results under the influence of microwave irradiation. α-Amidoalkylation of enamines was carried out successfully in the presence of (i-Pr)₂EtN in a microwave reactor. 1-(N-Acylamino)alkyltriphenylphosphonium salts can be considered as new, convenient and effective α-amidoalkylation agents.

Full text of DOI:10.1080/10426507.2012.744014

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Amidoalkylating Properties of 1-(N-
Acylamino)Alkyltriphenylphosphonium
Salts
Agnieszka Październiok-Holewa a , Jakub Adamek a , Roman
Mazurkiewicz a & Katarzyna Zielińska a
a Department of Organic Chemistry, Biochemistry and
Biotechnology , Silesian University of Technology, Krzywoustego 4 ,
PL 44-100 , Gliwice , Poland
Published online: 08 May 2013.
To cite this article: Agnieszka Październiok-Holewa , Jakub Adamek , Roman Mazurkiewicz &
Katarzyna Zielińska (2013) Amidoalkylating Properties of 1-(N-Acylamino)Alkyltriphenylphosphonium
Salts, Phosphorus, Sulfur, and Silicon and the Related Elements, 188:1-3, 205-212, DOI:
10.1080/10426507.2012.744014
To link to this article: http://dx.doi.org/10.1080/10426507.2012.744014
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Phosphorus, Sulfur, and Silicon, 188:205–212, 2013
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2012.744014
AMIDOALKYLATING PROPERTIES OF
1-(N-ACYLAMINO)ALKYLTRIPHENYLPHOSPHONIUM
SALTS
Agnieszka Paz´dzierniok-Holewa, Jakub Adamek,
Roman Mazurkiewicz, and Katarzyna Zielin´ska
Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian
University of Technology, Krzywoustego 4, PL 44-100 Gliwice, Poland
GRAPHICAL ABSTRACT
Abstract Easily accessible 1-(N-acylamino)alkyltriphenylphosphonium salts react smoothly
with nitrogen, sulfur, phosphorus and oxygen nucleophiles in the presence of (i-Pr)2EtN
to give the expected α-amidoalkylation products, usually in good or very good yields. α-
Amidoalkylation of dialkyl malonates or acetylacetates requires the application of a much
stronger base (DBU) and gives the best results under the influence of microwave irradiation.
α-Amidoalkylation of enamines was carried out successfully in the presence of (i-Pr)2EtN in
a microwave reactor. 1-(N-Acylamino)alkyltriphenylphosphonium salts can be considered as
new, convenient and effective α-amidoalkylation agents.
Keywords α-Amidoalkylation; 1-(N-acylamino)alkyltriphenylphosphonium salts; nucle-
ophilic substitution; enamines
Received 14 September 2012; accepted 23 October 2012.
The financial help of the Ministry of Science and Higher Education of Poland (Grant No. N N204 165636)
is gratefully acknowledged.
Address correspondence to Agnieszka Paz´dzierniok-Holewa, or Roman Mazurkiewicz, Department of Or-
ganic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, PL 44-100
Gliwice, Poland. E-mail: roman.mazurkiewicz@polsl.pl or agnieszka.pazdzierniok@polsl.pl
205

´
A. PAZDZIERNIOK-HOLEWA ET AL.
206
INTRODUCTION
α-Aminoalkylation and α-amidoalkylation reactions play an important role in or-
ganic synthesis, especially in pharmaceutical chemistry.1–5 The Mannich reaction, being
the best known aminoalkylation reaction, has two important limitations: (i) it is limited,
with few exceptions, to α-aminomethylation, and (ii) aminomethylation products (Mannich
bases) easily undergo various kinds of secondary reactions that are difficult to avoid.1,6,7
The α-amidoalkylation reaction can be considered as an important extension to the Man-
nich reaction.5,7 Numerous α-amidoalkylating reagents of a general structure 1 have been
reported, where X represents some nucleofugal leaving group, usually OH, OR, OCOR,
Cl, Br, NHCOR, SO2Ar, 1-benzotriazolyl or OTMS.5,7–10 Limitations and disadvantages
of α-amidoalkylation methods with the participation of most of the abovementioned ami-
doalkylating agents were reviewed by Katritzky et al.4,5,7 (Figure 1).
Recently, we have described three independent, efficient methods for the synthe-
sis of 1-(N-acylamino)alkyltriphenylphosphonium salts 6 (Scheme 1).11–15 In this paper,
we describe the application of 1-(N-acylamino)alkyltriphenylphosphonium salts 6 as new
versatile and effective amidoalkylating reagents for the α-amidoalkylation of a variety of
nucleophiles (Scheme 1).
RESULTS AND DISCUSSION
1-(N-Acylamino)alkyltriphenylphosphonium salts 6 react smoothly with nitrogen,
sulfur and oxygen nucleophiles with an active proton in the presence of catalytic amounts
of (i-Pr)2EtN (Hu¨nig’s base) at 60◦C or even at room temperature in a sealed glass vial to
give the expected α-amidoalkylation products 7, usually in good or even very good yields
(Scheme 1, Table I, Procedure A). However, in reaction with phenol, the reaction yield was
poor.
C H Acids, e.g., dialkyl malonates or acetylacetates, do not react with 1-(N-
acylamino)alkyltriphenylphosphonium salts 6 in the presence of the Hu¨nig’s base; the
amidoalkylation of these compounds can be carried out, however, in the presence of the
much stronger organic bases, e.g., DBU (Scheme 1, Table I, Procedure B). Application
of microwave irradiation accelerated reactions with C H acids and markedly improved
reaction yields.
α-Amidoalkylation of carbon nucleophiles with 1-(N-acylamino)alkyltriphenylphos-
phonium salts 6 was successfully extended to enamines. The reactions were carried out in
Figure 1

1-(N-ACYLAMINO)ALKYLTRIPHENYLPHOSPHONIUM SALTS
207
O
R2 O
Ph3P
Ph3P
R2Y
O
OY
R1
N
N
R1
2
3
HBF4
H2O
- CO2
O
MeOH,
base
-CO2
O
COOH
R2
O
OMe
R2
PPh3 Y
R2
O
Nu
R2
PPh3 HBF4
NuH, base
R1
N
R1
N
R1
N
R1
N
- PPh3
- B HY
H
H
H
H
5
6
7
4
Y = I, Br, BF4
Scheme 1
the presence of the Hu¨nig’s base under the influence of microwave irradiation (Scheme 2,
Table I, Procedure C).
Scheme 2
Reactions with trialkyl phosphites, dialkyl phosphonites and alkyl phosphinites gave
the expected product of the Michaelis-Arbuzov-like reaction in good to excellent yields
(Scheme 3, Table 1, Procedure D).
Scheme 3
The structures of obtained products were confirmed by their spectroscopic properties
(IR, 1H, 13C, and 31P NMR); in the case of all new compounds, we also obtained satisfactory
results of their elemental analyses.

208

1-(N-ACYLAMINO)ALKYLTRIPHENYLPHOSPHONIUM SALTS
209
CONCLUSIONS
In conclusion, easily accessible 1-(N-acylamino)alkyltriphenylphosphonium salts
can be considered as new, convenient and effective α-amidoalkylation reagents. In contrast
to many other α-amidoalkylating agents 1-(N-acylamino)alkyltriphenylphosphonium salts
are usually crystalline, stable, easy-to-use compounds, that can be stored for prolonged
time under laboratory conditions. They are easily activated as α-amidoalkylating reagents
with organic bases, which is more advantageous than the alternative usage of Lewis acids,
usually recommended as catalyst for α-amidoalkylation reactions.
EXPERIMENTAL
General
Melting points are determined in capillary tubes in a Stuart Scientific SMP3 melt-
ing point apparatus, and are uncorrected. IR spectra were recorded on a Zeiss Specord
1
M80 spectrophotometer. H and 13C NMR spectra were recorded in CDCl3 on a Varian
UNITY INOVA-300 spectrometer at operating frequencies of 300 and 75.5 MHz or on
a Varian 600 spectrometer at operating frequencies of 600 and 150.8 MHz, respectively,
in the FT mode using TMS as an internal standard. 31P NMR spectra were recorded
on a Varian 600 spectrometer at operating frequencies of 242.8 MHz, using 80% or-
thophosphoric acid as the resonance shift standard. Elemental analyses (C, H, N) proved
to be in satisfactory agreement ( 0.2%) with the calculated values. Reactions with ap-
plication of microwave irradiation were carried out using a CEM Matthews microwave
reactor. Kieselgel 60 (Merck, 0.063–0.200 mm) was used for column chromatography.
1-(N-Acylamino)alkyltriphenylphosphonium salts 6 were synthesized as described in our
previous paper.11–15
General Procedures for Reaction of 1-(N-acylamino)
alkyltriphenylphosphonium Salts 6 with Nucleophiles
Procedure A. Reactions were carried out in a glass vial sealed with a screw-cap.
To a solution of 1-(N-acylamino)alkyltriphenylphosphonium salt 6 (1 mmol) in 2.0 cm3 of
MeCN, a solution of nucleophilic reagent and diisopropylethylamine (in amounts given in
Table I) in 2 cm3 of MeCN was added. The mixture was kept at room temperature (7a)
or heated at 60◦C in an oil bath (7b-c, 7e) for the time given in Table I. Only in the case
of compound 7d the mixture was irradiated at a power of 8 W at 60◦C in a microwave
reactor. The solvent was evaporated under reduced pressure, and the product was isolated
by column chromatography [toluene/AcOEt (7a-b and 7d-e) or toluene/MeOH (7c)]. The
crystalline crude product was recrystallised from a mixture of toluene and hexane (7a, 7e),
CH2Cl2 (7b) or toluene (7c, 7d).
Procedure B. Reactions were carried out in a glass vial sealed with a screw-cap.
To a solution of 1-(N-acylamino)alkyltriphenylphosphonium salt 6 (1 mmol) in 4.0 cm3
of MeCN, a solution of nucleophilic reagent and DBU (in amounts given in Table I) in
4 cm3 of MeCN was added. The mixture was irradiated at a power of 10–12 W at 60◦C
in a microwave reactor for the time given in Table I. The solvent was evaporated under
reduced pressure, and the product was isolated by column chromatography (silica gel,
toluene/EtOAc). The crystalline crude compound 7f was recrystallised from toluene.

´
210
A. PAZDZIERNIOK-HOLEWA ET AL.
Procedure C. Reactions were carried out in a glass vial sealed with a screw-cap.
To a solution of 1-(N-acylamino)alkyltriphenylphosphonium salt 6 (1 mmol) in 2 cm3
of MeCN, a solution of 1-morpholino-1-cyclohexene (0.34 cm3, 0.34 g, 2 mmol) and
diisopropylethylamine (0.2 cm3, 0,15 g, 1.2 mmol) in 2 cm3 of MeCN was added. The
mixture was irradiated at a power of 8 W at 60◦C in a microwave reactor for 1 h. After
cooling to room temperature, 4.5 cm3 of the water solution of citric acid (20%) was added,
the suspension was stirred for 45 min, a saturated solution of KHCO3 was added, the
mixture was extracted with CH2Cl2 (4 × 4 cm3), the organic layer was dried (MgSO4), and
the solvent was evaporated under reduced pressure. Finally, the product was separated by
column chromatography [(toluene and AcOEt in a volume ratio of 1:1 (8a) or 2:1 (8b)] and
recrystallised from a mixture of toluene and hexane (8a) or toluene (8b).
Procedure D. Reactions were carried out in a glass vial sealed with a screw-cap.
To a solution of 1-(N-acylamino)alkyltriphenylphosphonium salt 6 (1 mmol) in 2.0 cm3
of CH2Cl2, methyltriphenylphosphonium iodide (0.10 g, 0.25 mmol), trimethyl phos-
phite, diethyl phenylphosphonite, diethyl ethylphosponite or methyl diphenylphosphinite
(1.25 mmol) and diisopropylethylamine (0.017 cm3, 0.013 g, 0.1 mmol) was added. The
mixture was heated at 60◦C for 2 h. The solvent was evaporated under reduced pressure
and the residue was extracted with toluene (3×1 cm3) at 50◦C. The solvent was evaporated
under reduced pressure, and the product was isolated by column chromatography (silica
gel, CH2Cl2/MeOH, 20:1 v/v or 40:1 v/v). The crude product was purified by crystallisation
(toluene/hexane).
Spectral and physical data for compounds 7a, 7e, 7f-7i and 9a-9d was described in
our previous papers.20–23
N-(Benzotriazol-1-ylmethyl)benzamide (7b)
1
IR (CH2Cl2), ν (cm−1): 3440, 1664, 1520. H NMR (300 MHz, CDCl3): δ = 8.58
(t, J = 6.6 Hz, 1H, NH), 8.04–7.26 (m, 9H, Ph and C6H4N3), 6.32 (d, J = 6.6 Hz, 2H,
CH2) ppm. 13C NMR (75.5 MHz, CDCl3): δ = 167.9 (CONH); 145.9, 132.5, 132.5, 132.2,
128.5, 127.9, 127.4, 124.4, 119.2, 111.1 (aromatic carbons); 51.5 (CH) ppm.
N-(Benzylaminomethyl)benzamide (7c)
IR (CH2Cl2), ν (cm−1): 3448, 1664, 1512, 1484. 1H NMR (300 MHz, CDCl3): δ =
7.74–7.21 (m, 10H, Ph), 6.85 (br s, 1H, NH), 4.42 (d, J = 5.7 Hz, 2H, NHCH2), 3.87 (s,
2H, HNCH2Ph), 2.28 (br s, HNCH2Ph) ppm. 13C NMR (75.5 MHz, CDCl3): δ = 168.0
(CONH); 139.8, 134.1, 131.6, 128.6, 128.5, 128.0, 127.1, 126.8 (aromatic carbons); 55.1
(NHCH2NH), 50.4 (PhCH2NH) ppm.
N-(Phenoxymethyl)benzamide (7d)
IR (CH2Cl2), ν (cm−1): 3448, 1680, 1600, 1516, 1484. 1H NMR (300 MHz, CDCl3):
δ = 7.80–7.77 (m, 2H, Ph), 7.55–7.40 (m, 3H, Ph), 7.33–7.26 (m, 2H, Ph), 7.03–6.97 (m,
3H, Ph and 1H, NH), 5.52 (d, J = 6.9 Hz, 2H, CH2) ppm. 13C NMR (75.5 MHz, CDCl3): δ =
167.4 (CONH); 156.5, 133.5, 132.1, 129.6, 128.7, 127.2, 121.8, 115.7 (aromatic carbons);
68.7 (CH2) ppm.

1-(N-ACYLAMINO)ALKYLTRIPHENYLPHOSPHONIUM SALTS
211
N-(2-Oxocyclohexylmethyl)benzamide (8a)
IR (CH2Cl2), ν (cm−1): 3452, 1704, 1660, 1520. 1H NMR (300 MHz, CDCl3): δ =
7.77–7.73 (m, 2H, Ph), 7.52–7.38 (m, 3H, Ph), 6.92 (br s, 1H, NH), 3.73 (ddd, J1 = 13.5 Hz,
J2 = 7.5 Hz, J3 = 3.6 Hz, 1H, HNCH2), 3.38 (ddd, J1 = 13.2 Hz, J2 = 8.1 Hz, J3 = 5.1 Hz,
1H, HNCH2), 2.73–2.62 (m, 1H, CH2CH), 2.45–1.38 (m, 8H, C5H9C O) ppm. 13C NMR
(75.5 MHz, CDCl3): δ = 214.0 (C5H9C=O), 167.1 (CONH); 134.4, 131.4, 128.5, 126.9
(aromatic carbons); 50.9 (HNCH2), 42.3 (CH2CH); 39.7, 31.8, 27.8, 24.8 (C5H9C O: C3,
C6, C4, C5) ppm. Elemental analysis Calcd. for C14H17NO2: C, 72.70; H, 7.41; N, 6.06;
Found: C, 72.57; H, 7.19; N, 6.02%.
N-[1-(2-Oxocyclohexyl)ethyl]benzamide (8b)
IR (CH2Cl2), ν (cm−1): 3440, 1704, 1660, 1512. 1H NMR (300 MHz, CDCl3): δ =
7.80–7.74 (m, 2H, Ph), 7.53–7.39 (m, 3H, Ph), 7.15 (d, J = 9.0 Hz, 1H, NH), 4.45–4.32
(m, 1H, HNCHCH3), 2.67–2.61(m, 1H, HNCHCH), 2.41–1.55 (m, 8H, C5H9C O), 1.35
(d, J = 6.9 Hz, 3H, CH3) ppm. 13C NMR (75.5 MHz, CDCl3): δ = 214.3 (C5H9C O),
166.6 (CONH); 134.6, 131.3, 128.5, 126.9 (aromatic carbons); 55.3 (HNCHCH3), 46.4
(HNCHCH); 43.2, 32.8, 28.3, 24.9 (C5H9C O: C3, C6, C4, C5); 20.1 (CH3) ppm. Elemental
analysis Calcd. for C15H19NO2: C, 73.44; H, 7.81; N, 5.71. Found: C, 73.48; H, 7.78; N,
5.73%.
Diphenyl 1-(N-pivaloylamino)ethylphosphine oxide (9e)
1
IR (CH2Cl2), ν (cm−1): 3259, 2969, 1647, 1528, 1438, 1177, 1119. H NMR
(300 MHz, CDCl3): δ = 7.86–7.42 (m, 10H, Ph), 6.30 (d, J = 9.3 Hz, 1H, NH), 5.23
(ddq, J1 = 9.9 Hz, J2 = 2.7 Hz, J3 = 7.2 Hz, 1H, CH), 1.33 (dd, J1 = 14.4 Hz, J2 =
7.2 Hz, 3H, CH3), 0.95 (s, 9H, t-Bu) ppm. 13C NMR (75.5 MHz, CDCl3): δ = 177.6 (d, J
= 4.5 Hz, C O); 132.1 (d, J = 3.0 Hz), 132.0 (d, J = 3.0 Hz), 131.0 (d, J = 9.0 Hz), 130.8
(d, J = 9.0 Hz), 130.5, 130.4, 128.8 (d, J = 10.6 Hz), 128.4 (d, J = 12.1 Hz) - aromatic
carbons; 42.5 (d, J = 78.4 Hz, CH), 38.6 (C(CH3)3), 27.1 (C(CH3)3), 14.5 (d, J = 3.0 Hz,
CH3) ppm. 31P NMR (242.8 MHz, CDCl3): δ = 35.1 ppm. Elemental analysis Calcd. for
C19H24NO2P: C, 69.28; H, 7.34; N, 4.25; P, 9.40. Found: C, 69.18; H, 7.33; N, 4.05; P,
9.36%.
Diphenyl 1-(N-Benzyloxycarbonylamino)-3-methylbutylphosphine
oxide (9f)
IR (CH2Cl2), ν (cm−1): 3191, 2955, 1705, 1542, 1438, 1264, 1185, 1119. 1H NMR
(300 MHz, CDCl3): δ = 7.85–7.12 (m, 15H, Ph), 5.45 (d, J = 10.5 Hz, 1H, NH), 5.02
(d, J = 12.6 Hz, 1H, OCH2), 4.89 (d, J = 12.6 Hz, 1H, OCH2), 4.83–4.71 (m, 1H, CαH),
1.83–1.66 (m, 2H, CβH2), 1.34–1.21 (m, 1H, Cγ H), 0.90 (d, J = 6.6 Hz, 3H, CH3), 0.86
(d, J = 6.6 Hz, 3H, CH3) ppm. 13C NMR (75.5 MHz, CDCl3): δ = 156.1 (d, J = 3.8 Hz,
C O); 136.4, 132.0 (d, J = 3.0 Hz), 131.9 (d, J = 2.3 Hz), 131.5, 131.3, 131.1 (d, J =
9.1 Hz), 131.0 (d, J = 9.1 Hz), 128.8 (d, J = 11.3 Hz), 128.4 (d, J = 11.3 Hz), 128.4, 127.9,
127.6 (aromatic carbons); 66.8 (OCH2), 48.0 (d, J = 79.3 Hz, CH), 37.4 (d, J = 3.0 Hz,
CβH2), 24.4 (d, J = 10.5 Hz, Cγ H), 23.4 (CH3), 21.0 (CH3) ppm. 31P NMR (242.8 MHz,
CDCl3): δ = 34.5 ppm. Elemental analysis Calcd. for C25H28NO3P: C, 71.24; H, 6.70; N,
3.32; P, 7.35. Found: C, 71.17; H, 6.87; N, 3.33; P, 7.20%.

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212
A. PAZDZIERNIOK-HOLEWA ET AL.
Diphenyl 1-(N-Benzyloxycarbonylamino)-2-t-butoxyethylphosphine
oxide (9g)
1
IR (CH2Cl2), ν (cm−1): 2974, 1706, 1542, 1438, 1270, 1240, 1181. H NMR
(300 MHz, CDCl3): δ = 7.89–7.17 (m, 15H, Ph), 5.68 (d, J = 9.6 Hz, 1H, NH), 5.03
(s, 2H, OCH2), 4.93–4.82 (m, 1H, CαH), 3.76 (ddd, J1 = 9.4 Hz, J2 = 9.3 Hz, J3 = 5.3 Hz,
1H, CβH), 3.89 (ddd, J1 = 14.4 Hz, J2 = 9.2 Hz, J3 = 5.3 Hz, 1H, CβH), 0.97 (s, 9H, t-Bu)
ppm. 13C NMR (75.5 MHz, CDCl3): δ = 156.0 (d, J = 5.3 Hz, C O); 136.3, 131.8 (d, J =
3.0 Hz), 131.7 (d, J = 2.3 Hz), 131.4 (d, J = 9.8 Hz), 131.1 (d, J = 9.8 Hz), 130.5, 130.4,
128.4, 128.4 (d, J = 11.3 Hz), 128.3 (d, J = 12.1 Hz), 128.0, 127.7 - aromatic carbons;
73.4 (C(CH3)3), 66.9 (OCH2), 60.1 (d, J = 3.8 Hz, CβH2), 50.6 (d, J = 80.0 Hz, CH), 27.0
(C(CH3)3) ppm. 31P NMR (242.8 MHz, CDCl3): δ = 31.9 ppm. Elemental analysis Calcd.
for C26H30NO4P: C, 69.17; H, 6.70; N, 3.10; P, 6.86. Found: C, 69.24; H, 6.82; N, 3.12; P,
6.73%.
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