Unexpected Products from Carbonylation of Lithiated Quinazolin-4(3H)-one Derivatives

Article abstract of DOI:10.1023/A:1025558201900

Doubly lithiated 3-pivaloylaminoquinazolin-4(3H)-one reacts with carbon(II) oxide at 0°C to give 77% of a mixture of azetidinone and indole derivatives, each incorporating a diisopropylamide unit from lithium diisopropylamide used for lithiation. No analogous reaction occurs with doubly lithiated 3-acetyl-aminoquinazolin-4(3H)-one and 3-acyl-2-alkylquinazolin-4(3H)- one. Carbonylation of doubly lithiated 2-alkyl-3-aminoquinazolin-4(3H)-ones at 0°C results in deamination to give 2-alkylquinazolin-4(3H)-ones in good yields.

Full text of DOI:10.1023/A:1025558201900

Russian Journal of Organic Chemistry, Vol. 39, No. 3, 2003, pp. 430 435. From Zhurnal Organicheskoi Khimii, Vol. 39, No. 3, 2003, pp. 457 462.
Original English Text Copyright 2003 by Smith, El-Hiti, Abdel-Megeed.
Dedicated to Full Member of the Russian Academy of Sciences
I.P. Beletskaya on Her Jubilee
Unexpected Products from Carbonylation of Lithiated
*
Quinazolin-4(3H)-one Derivatives
1
1
2
K. Smith , G. A. El-Hiti , and M. F. Abdel-Megeed
1
Center for Clean Chemistry, Department of Chemistry, University of Wales,
Swansea, SA2 8PP, UK
2
Department of Chemistry, Faculty of Science, Tanta University, Tanta 31527, Egypt
Received October 23, 2002
Abstract Doubly lithiated 3-pivaloylaminoquinazolin-4(3H)-one reacts with carbon(II) oxide at 0 C to give
7% of a mixture of azetidinone and indole derivatives, each incorporating a diisopropylamide unit from
7
lithium diisopropylamide used for lithiation. No analogous reaction occurs with doubly lithiated 3-acetyl-
aminoquinazolin-4(3H)-one and 3-acyl-2-alkylquinazolin-4(3H)-one. Carbonylation of doubly lithiated
2
-alkyl-3-aminoquinazolin-4(3H)-ones at 0 C results in deamination to give 2-alkylquinazolin-4(3H)-ones
in good yields.
Reactions of organolithium compounds with carbon
monoxide are rarely used in synthetic chemistry,
presumably because of the instability and high reac-
tivity of acyllithium intermediates which can lead to
a variety of products [1]. To circumvent this problem,
organic chemists have devised a number of acyl
carbanion equivalents which are effective in nucleo-
philic acylation reactions [2]. Seyferth et al. [3] have
shown that it is possible to trap acyllithium inter-
mediates formed by carbonylation of alkyllithium
reagents provided that the temperature is kept very
low and that the trapping electrophile can be used
in situ. However, the conditions are rather restrictive,
and the method has rarely been used with aryllithium
derivatives [4].
we have previously shown that doubly lithiated
N-pivaloylanilines and N-pivaloylaminopyridines I
smoothly react with carbon monoxide at 0 C under
atmospheric pressure to give 3-tert-butyldioxindoles
and 3-tert-butylazadioxindoles II in good yields as
a result of intramolecular trapping [6] (Scheme 1).
Carbon(II) oxide reacts in a similar way with doubly
lithiated N -aryl-N,N-dimethylthioureas to give indigo-
tins [7] and with lithiated N -aryl-N,N-dimethylureas
to give isatins [8].
We have also shown that doubly lithiated 3-(acyl-
amino)quinazolin-4(3H)-ones can be successfully
trapped with a variety of electrophiles [9 11]. Com-
pounds possessing this ring system exhibit versatile
biological activity [12]. Therefore, it was reasonable
to extend the range of electrophiles to include carbon
monoxide with a view to obtain some interesting
Better results are obtained when the incipient aryl-
lithium is trapped intramolecularly [5]. For example,
Scheme 1.
X = CH, N.
_
*
___________
The original article was submitted in English.
1
070-4280/03/3903-0430$25.00 2003 MAIK Nauka/Interperiodica

UNEXPECTED PRODUCTS FROM CARBONYLATION
431
Scheme 2.
fused quinazolinone derivatives by analogy with
Scheme 1. The present article reports on our attempts
at such reactions, which gave unexpected results.
to each other (J 5 Hz), and the third was coupled
to a CH doublet resonating at 4.19 ppm (J 7 Hz).
The spectrum clearly showed an isopropyl group and
two separate methyl groups in addition to the tert-
butyl group, as well as four aromatic protons of
an ortho-substituted benzene ring. The IR spectrum
showed two carbonyl groups, and the accurate mass
of the molecular ion in the mass spectrum indicated
3
-Pivaloylaminoquinazolin-4(3H)-one (III) was
doubly lithiated with LDA and was then brought into
reaction with carbon(II) oxide at 0 C under atmos-
pheric pressure. The subsequent protonation gave
two new products. They were purified by column
chromatography and were identified as azetidinone
derivative IV and substituted indole V (Scheme 2).
1
3
a formula of C H N O . The C NMR spectrum of
2
0
30
4
3
IV contained 18 different signals, only the three
methyl groups of the tert-butyl group being degen-
erate. These data are consistent with the proposed
structure.
1
The H NMR spectrum of compound IV showed
three exchangeable doublets resonating in the 7.92
9.24 ppm region. Two of these signals were coupled
Scheme 3.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 3 2003

4
32
SMITH et al.
Scheme 4.
1
The H NMR spectrum of compound V showed
four exchangeable singlets resonating in the 9.24
0.16 ppm region. It also showed the presence of two
oxide molecules, repectively. However, Schemes 3
and 4 show plausible pathways for their formation.
Here, the key step which causes the reaction to
deviate from the path predominating in reactions with
pivaloylaminobenzenes is ring opening of the lithiated
quinazoline ring of intermediate VI. The subsequent
carbon(II) oxide uptake gives intermediate VII.
1
identical isopropyl groups in addition to the tert-butyl
group and only three aromatic protons corresponding
to a 1,2,3-trisubstituted benzene ring. The accurate
mass of the molecular ion in the mass spectrum
indicated a molecular formula of C N N O which
2
1
30
4
4
An attempt was made to extend the reaction to
-acetylaminoquinazolin-4(3H)-one. However, its
could be accounted for by incorporation of a second
carbon(II) oxide unit over and above that required
for formation of IV. Apart from the signals due to
the tert-butyl and isopropyl groups, all carbons
3
doubly lithiated derivative failed to take up carbon(II)
oxide under analogous conditions, and the starting
material was recovered from the reaction mixture.
Presumably, initial deprotonation of the acetylamino
group yields a relatively unreactive enolate anion.
No further attempts were made to find conditions
under which this carbonylation could be successful.
1
3
resonated at separate positions in the C NMR spec-
1
13
trum. The observed chemical shifts ( H and C) for
compounds IV and V were in reasonable agreement
with those estimated using ChemDraw.
We have not studied the mechanisms of the reac-
tions leading to compounds IV and V which are
formed via incorporation of one or two carbon(II)
We have previously shown that 2-alkyl-3-acyl-
aminoquinazolin-4(3H)-ones [9, 10] and 2-alkyl-3-
aminoquinazolin-4(3H)-ones [11] are readily doubly
Scheme 5.
VIII, XI, R = H; IX, XII, R = Me; X, XIII, R = Et.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 3 2003

UNEXPECTED PRODUCTS FROM CARBONYLATION
433
Scheme 6.
lithiated and that their dilithium derivatives are
capable of successfully reacting with a variety of
electrophiles. Attention was therefore turned to the
carbonylation of these doubly lithiated compounds.
Doubly lithiated 3-acylamino-2-alkylquinazolin-
are based on coupling patterns and expected chemical
shift values and have not been rigorously confirmed.
Signals with similar characteristics might be inter-
changed. The low-resolution mass spectra were
recorded on a VG 12-253 spectrometer under electron
impact (EI) at 70 eV and chemical ionization (CI)
using ammonia as ionizing gas. The accurate mass
data were obtained on a VG ZAB-E instrument. The
elemental analyses were obtained from the laboratories
of the University of Wales, Cardiff. Column chroma-
tography was carried out using Merck Kieselgel 60
4
(3H)-ones failed to take up carbon(II) oxide. How-
ever, doubly lithiated 2-alkyl-3-aminoquinazolin-
(3H)-ones VIII X did react with carbon(II) oxide
4
at 0 C, surprisingly giving the corresponding 2-alkyl-
quinazolin-4(3H)-ones XI XIII in 61 69% yield
(
isolated product; Scheme 5).
The H NMR spectra of compounds XI XIII were
1
(230 400 mesh). Butyllithium and lithium diiso-
propylamide were obtained from Aldrich; butyllithium
was estimated prior to use by the method of Watson
and Eastham [14]. Tetrahydrofuran was distilled over
sodium diphenylketyl. The other chemicals were
obtained from Aldrich and were used without further
purification. The solvents were purified by standard
techniques [15, 16].
characterized by the presence of an exchangeable
singlet resonating at 12.2 ppm, which was assigned
to the quinazolinone NH proton. Compounds XI XIII
were found to be identical in all respects to authentic
samples prepared as described in [13]. A plausible
mechanism of the reaction leading to products XI
XIII is shown in Scheme 6. The mechanism presumes
elimination of isocyanate ion.
Carbonylation of 3-pivaloylaminoquinazolin-
4
(3H)-one (III). A solution of 0.245 g (1.0 mmol) of
Thus the carbonylation of doubly lithiated quinazo-
lin-4(3H)-one derivatives occurs in a way different
from the carbonylation of doubly lithiated N-pivaloyl-
anilines or N-pivaloylaminopyridines. Unexpected
products were isolated from the reactions of doubly
lithiated 3-pivaloylaminoquinazolin-4(3H)-one and
quinazolinone III and 2.06 ml (3.3 mmol) of lithium
diisopropylamide in 10 ml of THF was stirred for 1 h
at 78 C under argon. The temperature was slowly
allowed to rise to 0 C. A balloon filled with carbon(II)
oxide ( 500 ml) was fitted to a needle, and CO was
allowed to bleed into the reaction mixture. After
2-alkyl-3-aminoquinazolin-4(3H)-ones with carbon(II)
2
h, the solution was poured into a saturated solution
oxide.
of NH Cl (10 ml), and the mixture was extracted
4
with ethyl acetate (20 ml). The organic layer was
EXPERIMENTAL
washed with 10 ml of water, dried over MgSO , and
4
evaporated under reduced pressure. The residue was
purified by column chromatography using ether
hexane (80:20 by volume) to isolate 0.162 g (43%)
of azetidinone IV and 0.137 g (34%) of indole V.
The melting points were determined on an electro-
thermal digital melting point apparatus and are uncor-
rected. The IR spectra were recorded on a Perkin
1
13
Elmer 1725X spectrometer. The H and C NMR
spectra were recorded on a Bruker spectrometer
4,4-Dimethyl-1-(1-methylethyl)-3-(2-pivaloyl-
hydrazinocarbonylphenylamino)azetidin-2-one
1
13
operating at 400 MHz for H and 100 MHz for C.
The chemical shifts are reported in parts per million
relative to tetramethylsilane. Assignments of signals
1
(IV). mp 200 201 C. IR spectrum (KBr), , cm :
1
3305, 1725, 1678, 1641, 1602, 1581, 1509. H NMR
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 3 2003

4
34
SMITH et al.
spectrum (CDCl ), , ppm (J, Hz): 9.24 br.d (1H,
CONHNH, J = 4.8), 8.91 br.d (1H, CONHNHCO-
Bu-t, J = 4.8), 7.93 br.d (1H, NHCH, J = 6.6),
solution of NH Cl (10 ml), and the mixture was
3
4
extracted with ethyl acetate (20 ml). The organic layer
was washed with 10 ml of water, dried over MgSO4,
and evaporated under reduced pressure. The residue
was purified by column chromatography using ether
hexane (80:20 by volume) as eluent to isolate com-
pounds XI XIII as white crystals in 61 69% yields.
7
.57 d.d (1H, 3 -H, J = 1.4, 7.9), 7.27 d.t (1H, 5 -H,
J = 1.4, 7.9), 6.67 d.t (1H, 4 -H, J = 1.4, 7.9), 6.46 d
1H, 6 -H, J = 7.9), 4.19 d (1H, 3-H, J = 6.6),
(
3
1
.58 sept [1H, CH(CH ) , J = 6.9], 1.56 s (3H, CH ),
3 2 3
.34 d and 1.32 d [6H, CH(CH ) , J = 6.9], 1.28 s
2-Methylquinazolin-4(3H)-one (XI). mp 239 C;
3
2
1
3
published data [13]: mp 238 239 C. IR spectrum
[9H, C(CH ) ], 1.25 s (3H, CH ). C NMR spectrum
3 3 3
1
2
(
KBr), , cm : 3318, 1677, 1610, 1566, 1504.
(
CDCl3), , ppm: 175.6 s (COBu-t); 166.6 s (C );
C
1
5
1
165.1 s (CONHNH); 148.3 s (C ); 133.4 d (C );
H NMR spectrum (DMSO-d6), , ppm (J, Hz):
3
4
2
1
28.0 d (C ); 116.5 d (C ); 113.4 s (C ); 111.9 d
12.21 br.s (1H, NH), 8.08 d.d (1H, 5-H, J = 1.0, 7.9),
7.74 d.t (1H, 7-H, J = 1.0, 7.9), 7.55 d (1H, 8-H, J =
7.9), 7.43 d.t (1H, 6-H, J = 1.0, 7.9), 2.36 s (3H,
6
3
4
(C ); 68.3 d (C ); 62.7 s (C ); 44.4 d [CH(CH ) ];
3 2
3
2
3
8.2 s [C(CH ) ]; 27.2 q, 25.5 q, 21.9 q, 21.7 q, and
3 3
1
3
1.1 q [C(CH ) ]. Mass spectrum, m/z (I , %): EI:
CH3). C NMR spectrum (DMSO-d ),
, ppm:
3
2
rel
6
C
+
4
2
8a
7
74 M (4), 347 (2), 289 (17), 173 (30), 100 (100), 57
1
1
(
61.7 s (C ), 154.1 s (C ), 149.0 s (C ), 134.1 d (C ),
26.5 d (C ), 125.8 d (C ), 125.7 d (C ), 120.7 s
C ), 21.43 q (CH ). Mass spectrum, m/z (I , %):
EI: 160 M (100), 147 (20), 119 (60), 92 (65), 64
+
(45); CI: 375 MH (100), 347 (5), 276 (12), 100 (22).
5
6
8
+
Found: M 374.2318; calculated for C H N O :
4a
2
0
30
4
3
3 rel
3
74.2318. Found, %: C 64.0; H 8.1; N 15.1. Calcu-
lated, %: C 64.17; H 8.02; N 14.97.
-Diisopropylaminocarbonyl-3-hydroxy-7-piva-
+
+
(
40). Found: M 160.0637. Calculated for C H N O:
9 8 2
2
1
60.0637. Found, %: C 67.3; H 5.2; N 17.7. Calcu-
loylhydrazinocarbonylindole (V). mp 223 224 C.
lated, %: C 67.50; H 5.00; N 17.50.
-Ethylquinazolin-4(3H)-one (XII). mp 236 C;
published data [13]: mp 235 C. IR spectrum (KBr),
1
IR spectrum (KBr), , cm : 3437, 1692, 1662, 1600,
2
1
1
575, 1544. H NMR spectrum (DMSO-d ), , ppm
6
1
1
(J, Hz): 10.16 br.s (1H, OH), 9.83 br.s (1H, NH),
,
cm : 3313, 1681, 1611, 1565, 1505. H NMR
9
.50 br.s (1H, CONHNH), 9.24 br.s (1H, CONHNH-
spectrum (DMSO-d6), , ppm (J, Hz): 12.17 br.s
COBu-t), 7.89 d (1H, 4-H, J = 7.9), 7.86 d (1H, 6-H,
J = 7.9), 7.03 t (1H, 5-H, J = 7.9), 4.08 br {2H,
(
(
1H, NH), 8.08 d.d (1H, 5-H, J = 1.0, 7.9), 7.75 d.t
1H, 7-H, J = 1.0, 7.9), 7.59 d (1H, 8-H, J = 7.9),
[
CH(CH ) ] }, 1.41 d {12H, [CH(CH ) ] , J = 6.7}
3 2 2 3 2 2
7.44 d.t (1H, 6-H, J = 1.0, 7.9), 2.36 q (2H, CH ,
2
1
3
13
and 1.29 s [9H, C(CH ) ]. C NMR spectrum
J = 7.5), 1.28 t (3H, CH , J = 7.5). C NMR spec-
3
3
3
4
2
(
DMSO-d6),
, ppm: 177.7 s (COBu-t), 166.7 s
trum (DMSO-d ), , ppm: 161.8 s (C ), 158.2 s (C ),
C
6 C
8
a
7
5
7
a
1
(
(
48.9 s (C ), 134.0 d (C ), 126.7 d (C ), 125.7 d
(CONHNH), 163.5 s (COPr-i), 138.3 s (C ), 132.6 s
6
8
4a
2
4
5
3a
C ), 125.6 d (C ), 120.7 s (C ), 26.5 t (CH ), 11.3 q
(
1
{
C ), 123.6 d (C ), 123.2 d (C ), 120.4 s (C ),
2
+
6
3
7
CH ). Mass spectrum, m/z (I , %): EI: 175 MH
17.6 d (C ), 114.7 s (C ), 114.2 s (C ), 47.8 d
3
rel
+
[CH(CH ) ] }, 38.0 s [C(CH ) ], 27.4 q [C(CH ) ]
(40), 174 M (100), 146 (12), 119 (16); CI: 175
MH , (100). Found: M 174.0793. Calculated for
3
2 2
3 3
3 3
+
+
and 21.1 q [CH(CH ) ]. Mass spectrum, m/z (I , %):
3
2
rel
+
EI: 402 M (35), 360 (10), 244 (30), 186 (17), 102
55), 57 (100); CI: 403 MH (100), 304 (20), 130 (30).
Found: M 402.2267; calculated for C H N O :
C H N O: 174.0793. Found, %: C 68.7; H 5.8;
1
0
10
2
+
(
N 16.1. Calculated, %: C 68.96; H 5.75; N 16.09.
+
2
1
30
4
4
2-Propylquinazolin-4(3H)-one (XIII). mp 207 C;
4
02.2267. Found, %: C 62.6; H 7.6; N 13.9. Calcu-
published daa [13]: mp 206 207 C. IR spectrum
1
lated, %: C 62.68; H 7.46; N 13.93.
(
KBr), , cm : 3400, 1668, 1609, 1565, 1504.
1
Carbonylation of 2-alkyl-3-aminoquinazolin-
H NMR spectrum (DMSO-d6), , ppm (J, Hz):
4
(3H)-ones VIII X. A solution of BuLi (in the case
of compound VIII) or LDA (IX and X) (1.6 M,
.06 ml, 3.3 mol) was added dropwise with stirring
1
7
7
2.16 br.s (1H, NH), 8.08 d.d (1H, 5-H, J = 1.0, 7.9),
.75 d.t (1H, 7-H, J = 1.0, 7.9), 7.58 d (1H, 8-H, J =
.9), 7.44 d.t (1H, 6-H, J = 1.0, 7.9), 2.58 t (2H,
2
under nitrogen to a solution of 1.0 mmol of the corre-
sponding 2-alkyl-3-aminoquinazolin-4(3H)-one in
CH CH CH , J = 7.5), 1.77 sext (2H, CH CH , J =
2
2
3
2
3
13
7
(
1
.5), 0.96 t (3H, CH , J = 7.5). C NMR spectrum
DMSO-d ), , ppm: 161.8 s (C ), 157.1 s (C ),
48.9 s (C ), 134.0 d (C ), 126.7 d (C ), 125.7 d (C ),
125.6 d (C ), 120.8 s (C ), 36.3 t (CH CH CH ),
3
2
0 ml of THF. The mixture was stirred for 45 min at
4
2
6
8
7
8 C and was allowed to slowly warm up to 0 C.
a
7
5
6
Carbon(II) oxide was bled into the mixture by attach-
ment of a balloon filled with the gas through a needle.
After 2 h, the solution was poured into a saturated
8
4a
2
2
3
20.2 t (CH CH ), 13.4 q (CH ). Mass spectrum, m/z
2
3
3
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 3 2003

UNEXPECTED PRODUCTS FROM CARBONYLATION
435
+
+
(
1
I , %): EI: 189 MH (100), 160 (12). Found: MH
and Murai, S., Organometallics, 1996, vol. 15,
p. 5459; Kai, H., Yamauchi, M., and Murai, S.,
Tetrahedron Lett., 1997, vol. 38, p. 9027; Ryu, I.,
Matsu, K., Minakata, S., and Komatsu, M., J. Am.
Chem. Soc., 1998, vol. 120, p. 5838; Ryu, I., Chem.
Soc. Rev., 2001, vol. 30, p. 16.
rel
89.1028. Calculated for C H N O: 189.1028.
Found, %: C 70.2; H 6.4; N 14.9. Calculated, %:
C 70.21; H 6.38; N 14.89.
11 13 2
G.A. El-Hiti thanks the University of Wales Swan-
sea for financial support and the Royal Society of
Chemistry for an international author grant. We thank
the EPSRC Mass Spectrometry Service, University of
Wales Swansea, for recording mass spectra for us.
We also thank EPSRC and the University of Wales
for grants that enable the purchase of NMR equipment
used in the course of this work.
6
7
.
.
Smith, K. and Pritchard, G.J., Angew. Chem., 1990,
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Trans. 1, 1999, p. 2299.
Smith, K., Shukla, A.P., and Matthews, I., Sulfur
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