One-pot synthesis of some new indene derivatives by thermal isomerization of iminolactones

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Organic Preparations and Procedures
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One-pot Synthesis of Some New Indene
Derivatives by Thermal Isomerization of
Iminolactones
A. Zonouzi a , H. Rahmani b , A. Kamali a & M. Biniaz a
a School of Chemistry , University College of Science, University of
Tehran , Tehran, Iran
b Institute of Chemical Technologies , Iranian Research Organization
for Science and Technology (IROST) , P.O. Box 15815-3538, Tehran,
Iran
Published online: 09 Jun 2011.
To cite this article: A. Zonouzi , H. Rahmani , A. Kamali & M. Biniaz (2011) One-pot Synthesis of
Some New Indene Derivatives by Thermal Isomerization of Iminolactones, Organic Preparations and
Procedures International: The New Journal for Organic Synthesis, 43:3, 276-284
To link to this article: http://dx.doi.org/10.1080/00304948.2011.581998
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Organic Preparations and Procedures International, 43:276–284, 2011
Copyright © Taylor & Francis Group, LLC
ISSN: 0030-4948 print / 1945-5453 online
DOI: 10.1080/00304948.2011.581998
One-pot Synthesis of Some New Indene Derivatives
by Thermal Isomerization of Iminolactones
A. Zonouzi,1 H. Rahmani,2 A. Kamali,1 and M. Biniaz1
1School of Chemistry, University College of Science, University of Tehran,
Tehran, Iran
2Institute of Chemical Technologies, Iranian Research Organization for Science
and Technology (IROST) P.O. Box 15815-3538, Tehran, Iran
The indene moiety found in many natural products,1 has attracted interest due to its possible
practical applications.2,3 For example, some substituted indene derivatives exhibit biological
activities such as fungicidal,4 selective estrogen receptor modulation,5,6 anti-proliferative7
and D2-like dopamine receptor agonists.8 Various methods for the synthesis of indene
derivatives have been reported.9–14 We now describe a one-pot reaction of acetylenic esters
and cyclohexyl isocyanide with aryl ketones to produce highly functionalized indenes 2a-f
in high yields (83–88%).
It had been previously established that one-pot and multi-component reactions of
alkyl isocyanides, carbonyl compounds and acetylenic esters produce heterocyclic com-
pounds.15–22 However, in the present work the indene derivatives 2 are produced and it is
postulated that the heterocyclic intermediates 1 that were formed initially in the reaction
are converted to indenes 2. Accordingly, to assess the validity of this postulate we decided
to isolate the intermediates 1. Thus, after cooling the reaction mixtures, the iminolactones
1 (the synthesis of 1a had been reported previously22) were purified and their structure
deduced by spectroscopic data. When these compounds 1 were refluxed in p-xylene for
35–48 h, indenes 2 were produced nearly quantitatively. The intramolecular N H---O
hydrogen bonding stabilized the products.23 (Scheme 1)
Solvents have been shown to have an important effect on this reaction. Thus, in
refluxing benzene (bp 80◦C) only iminolactones 1 were obtained in less than 30% yields
and no indenes 2 were obtained, Nair and coworkers had already reported the exclusive
formation of iminolactone 1a using benzene at 80◦C in 41% yield.21,22 In this study, we
have found that in refluxing toluene (bp 110◦C), iminolactones 1 were obtained in less than
50% yield and indenes 2 in less than 10% yield. In refluxing p-xylene (bp 138◦C), only
indenes 2 were obtained in 83–88% yield without any iminolactones 1. This reaction did
Received July 17, 2009; in final form November 26, 2010.
Address correspondence to A. Zonouzi, School of Chemistry, University College of Science,
University of Tehran, Tehran, Iran. E-mail: zonouzi@khayam.ut.ac.ir
276

One-pot Synthesis of Some New Indene Derivatives
277
Scheme 1
not proceed in acidic solvents and indeed Schmiar and coworkers had previously reported
that iminolactones are hydrolyzed to other products in acidic solvents.24
We suggest the following mechanism for the overall tranformation involving the con-
version of intermediates 1 to indenes 2 via a ring opening-ring closure mechanism. Such a
ring opening-ring closure mechanism has been reported previously for other heterocyclic
frameworks25–28 including a furan to indole process.25 Several attempts to intercept the
putative zwitterions 3 as carbocations (Scheme 2) with amines, thiols and phenols and
the anion of acetylacetone, were unsuccessful; thus, if this mechanism is operative, the
conversion of 1 to 2 must be rapid and quantitative.
Scheme 2
Structures 1 and 2 were assigned on the basis of their elemental analysis, IR, 1H and 13
C
NMR and mass spectral data. The mass spectra of these compounds displayed molecular
ion peaks at appropriate m/z values. For iminolactones 1, initial fragmentation involving
the loss of C6H11N, CH3OH for 1c, 1e and C6H11N, C2H5OH for 1b, 1d and 1f. For
indenes 2, fragments involves M+- C6H11NCO and M+- C6H11NCO, RꢀOH were the most
1
intense signals. The H NMR spectra of the products 2b, 2d and 2f clearly indicated the
diasterotopic CH2 protons of the ester groups on the C1 of indenes (Table 3). The IR spectra
of compounds 2a-f showed N H absorptions 3327–3353 cm−1, which did not change
upon dilution with CCl4, evidence of intramolecular hydrogen bonding. The intramolecular
N H···O hydrogen bond for indene 2b was detected and its details have been published.23

278
Zonouzi et al.
All compounds showed C O absorptions (1715–1732, 1670–1679 cm−1) and there were
also two absorptions for the NO2 groups in compounds 2a-d (1339–1344, 1449–1525
cm−1). The IR spectra of compounds 1b-f showed C O absorptions (1740–1755 cm−1
,
1719–1731 cm−1), C N absorption (1674–1682 cm−1) and C O absorptions (1253–1284,
1087–1129, 1020–1028 cm−1). Additionally there were two absorptions for the NO2 groups
in compounds 1b-d (1524–1533, 1339–1353 cm−1).
Overall we have developed a one-pot synthesis of some new indene derivatives via
an interesting isomerization reaction. The reaction described here represents a simple
and efficient entry into the synthesis of highly functionalized indenes. High yields and
simple conditions make it a useful addition to the modern synthetic methodologies. In
this procedure, intermediates 1 can be isolated in high yields through modifications in the
reaction conditions. These compounds 1 belong to the iminolactone family and some of
their derivatives act as antibacterial agents, aldosterone inhibitors and as precursors for the
preparation of a wide spectrum of natural compounds.29,30 Further investigations of this
method are currently in progress to establish its scope and utility.
Experimental Section
Chemicals and solvents were obtained from Merck (Germany) and Fluka (Switzerland)
and were used without further purification. Column chromatography was performed on
silica gel (0.015–0.04 mm, mesh-size) and TLC on precoated plastic sheets (25 DCUV-254).
Melting points were measured on a Barnstead Electrothermal melting point apparatus and
are not corrected. Elemental analyses for C, H and N were performed using a Thermo
Finnigan Flash EA1112 instrument. IR spectra were measured on a Shimadzu FT-IR-4300
spectrophotometer as KBr discs. 1H NMR and 13C NMR spectra were determined in CDCl3
on a Brucker 500 spectrophotometer and chemical shifts were expressed in ppm downfield
from tetramethylsilane. Mass spectra were recorded on a Finnigan-MAT 8430 spectrometer
at an ionization potential of 70 ev.
Dimethyl 1-(Cyclohexylcarbamoyl)-3-methyl-6-nitro-1H-indene-1,2-dicarboxylate (2a).
General Procedure
To a stirred solution of 4-nitroacetophenone (0.33 g., 2 mmol) and dimethyl acetylenedi-
carboxylate (0.28 g., 2 mmol) in p-xylene (15 mL) was added a mixture of cyclohexyl
isocyanide (0.22 g., 2 mmol) in p-xylene (10 mL) dropwise at -10◦C over 2 h. The reaction
mixture was stirred for 2 h at room temperature and then refluxed for 36 h. The reaction
was monitored by TLC, when the intermediate spots (Rf ≈ 0.2 on silica gel, n-hexane:ethyl
acetate 4:1) disappeared, the reaction was complete (indene spot: Rf = 0.6 on silica gel,
n-hexane: ethyl acetate 4:1). The solvent was removed under reduced pressure and the
residue was washed with n-hexane and recrystallized from acetone-ethyl acetate. The prod-
uct (0.724 g., 87%) was obtained as colorless crystals, mp. 134–135◦C. The same procedure
was used to prepare 2b-f as colorless crystals in of 83–88% yields.
Dimethyl 1-(Cyclohexylcarbamoyl)-3-methyl-6-nitro-1H-indene-1, 2-dicarboxylate (2a)
from 1. General Procedure
A magnetically stirred solution of the imino-lactone 1 (0.83 g., 2 mmol) in p-xylene
(50 mL) was refluxed for 32–45 h. The reaction was monitored by TLC. When the

One-pot Synthesis of Some New Indene Derivatives
279
Table 1
Spectroscopic Data of 1b-f
Cmpd
1H NMR (δ:ppm)
13C NMR (δ:ppm)
14.20, 14.45 (2 CH3 of CO2Et); 444 (M+, 13)
MS (m/z)
1b
1.24–2.12 (10H, 3m, CH2
of cyclohexyl); 1.27,
1.41 (6H, 2t, 2CH3 of
CO2Et); 2.12 (3H, s,
CH3); 3.68–3.69 (1H, m,
CH of cyclohexyl); 4.18-
4.21, 4.40–4.45 (4H, 2q,
J = 13.81,
24.17, 25.14, 26.14 (CH2 of
cyclohexyl); 33.79 (CH3);
57.01 (CH of cyclohexyl);
62.44, 62.73 (CH2 of
415 (M+-C2H5, 30)
398 (m+-C2H5OH, 75)
315 (M+- C6H11N,100)
CO2Et); 89.32 (C CH3);
124.06, 127.48 (CH of
C6H4); 136.38, 148.23
6.91 Hz, 2 CH2 of
(Cipso (C
of C6H4); 145.74,
C)
CO2Et); 7.63- 7.66,
8.25–8.27 (4H, 2m,
Ar protons)
147.13 (2 C CO2Et); 154.70
(C N-cyclohexyl); 160.85,
162.29 (2 C O of CO2Et)
1c
1d
1e
1.24–1.82 (10H, 4m, CH2
of cyclohexyl); 2.13 (3H,
s, CH3); 3.67–3.70 (1H,
m, CH of cyclohexyl);
3.77, 3.96 (6H, 2s, CH3
of CO2Me); 7.58–7.61
(1H, t, Ar proton);
24.77, 25.20, 26.11 (CH2 of
cyclohexyl); 33.73 (CH3);
53.27, 53.54 (2CH3 of
CO2Me); 57.19 (CH of
cyclohexyl); 89.24 (C CH3);
121.56, 123.93, 130.03,
132.38 (CH of C6H4);
416 (M+, 7)
304 (M+-CH3, 15)
384 (M+-CH3OH, 73)
287 (M+-C6H11N, 100)
7.76–7.78 (1H, d, J =
127.85, 134.19 (Cipso(c of
c)
8.01Hz, Ar proton);
C6H4); 146.00, 148.74
(2C CO2Me);
154.55(C N-cyclohexyl);
8.23–8.24 (1H, d, J =
8.01 Hz, Ar proton); 8.36
(1H, s, Ar proton)
161.23, 162.70 (2 C
of CO2Me)
O
1.23–1.81(10H, m, CH2 of 14.23, 14.71 (2 CH3 of
444 (M+, 11)
cyclohexyl); 1.26, 1.38
(6H, 2t, 2 CH3 of
CO2Et); 2.12 (3H, s,
CH3); 3.68 (1H, m, CH
of cyclohexyl);
4.16-4.21,4.40–4.44
(4H,2q, J = 14.02,
6.99 Hz, 2CH2 of
CO2Et); 7.58- 7.61,
7.61–7.73, 7.73–7.78,
8.23–8.36
CO2Et);24.66,25.01,26.11
(CH2 of cyclohexyl); 33.79
(CH3); 56.98 (CH of
cyclohexyl); 62.30, 62.79
(CH2 of CO2Et); 89.24
(C CH3);121.49, 123.91,
127.85, 130.03, 132.38,
134.19(Ar carbons); 146.85,
148.56 (2 C CO2Et); 154.59
(C N-cyclohexyl);
415 (M+-C2H5, 28)
398 (M+-C2H5OH, 74)
315 (M+-C6H11N, 100)
161.24, 162.78 (2 C
of CO2Et)
O
(4H, 4m, Ar protons)
1.22–1.36, 1.42–1.46,
1.64–1.81 (10H, 3m,
CH2 of cyclohexyl); 2.11
(3H, s, CH3); 3.64–3.68
(1H, m, CH of
cyclohexyl); 3.75, 3.94
(6H, 2s, CH3 of CO2Me);
7.06–7.07, 7.15–7.16
(4H, 2m, Ar protons)
24.63, 25.21, 26.10 (cyclohexyl 405, 407 (M+, M+2, 15, 5)
carbons); 33.76 (CH3); 53.35, 390, 392 (M+, M++2-CH3,
53.61 (2 CH3 of CO2Me);
57.21 (CH of cyclohexyl);
89.47 (C CH3); 124.67,
127.45 (CH of C6H4);
28, 9)
373, 375 (M+, M++
2-CH3OH, 78, 28)
276,278 (M+, M++
of 2-C6H11N, 100, 37)
130.37, 138.25 (C ipso (C
C)
C6H4); 136.112, 136.85 (2
CO2Me); 154.63
(C N-cyclohexyl);161.52,
162.73 (2 C O of CO2Me)
C
(Continued on next page)

280
Zonouzi et al.
Table 1
Spectroscopic Data of 1b-f (Continued)
Cmpd
1H NMR (δ:ppm)
13C NMR (δ:ppm)
MS (m/z)
1f
1.23–1.81 (10 H, 4m, CH2 14.20, 14.67 (2 CH3 of CO2Et); 433, 435 (M+, M++2, 16, 6)
of cyclohexyl); 1.27,
1.36 (6H, 2t, 2 CH3 of
CO2Et); 2.136 (3H, s,
CH3); 3.68 (1H, m, CH
of cyclohexyl);
24.73, 25.40, 26.28 (CH2 of
cyclohexyl); 32.69 (CH3);
57.35 (CH of cyclohexyl);
62.64, 63.30 (CH2 of CO2Et);
88.98 (C CH3); 124.84,
404, 402 (M+, M++2-C2H5,
29, 9)
387, 389 (M+, M++2
-C2H5OH, 8, 30)
304, 306 (M+, M++2
-C6H11N, 100, 38)
4.186–4.23, 4.40–4.45
(4H, 2q, J = 14.36,
7.11 Hz, 2 CH2 of
CO2Et); 7.05 – 7.07,
7.13–7.15 (4H, 2m,
Ar protons)
127.25 (CH of C6H4); 130.47,
135.69 (Cipso(C
of C6H4);
C)
136.14, 138.65 (2 C CO2Et);
154.63 (C N-cyclohexyl);
161.26, 162.62 (2 C O of
CO2Et)
iminolactone spot disappeared, the thermal interconversion of 1 into 2 was complete.
At this stage, the solvent was removed under reduced pressure. The same procedure for
the purification of 2a-f was performed as for the one-pot procedure. Although the purified
2a-f were obtained in 96–99% yields, the yields of indenes 2 reported in Table 4 are those
obtained in the one-pot reaction which is simpler and more convenient.
Compounds 1b-f which were not previously described in references 21 and 22, can be
obtained in 85–90% yields by the following procedure.
Synthesis of Compounds 1b-f. General Procedure
To a stirred solution of the acetophenone derivative (2 mmol) and dialkyl acetylenedicar-
boxylate (2 mmol) in p-xylene (15 mL) was added a mixture of alkyl isocyanide (2 mmol)
in p-xylene (10 mL) dropwise at -10◦C over 2 h. The reaction mixture was warmed to 75◦C
and stirred at 75◦C for 10 h then allowed standing in a refrigerator for 24 h. The solvent was
removed under reduced pressure and the residue was purified by column chromatography
(silica gel, n-hexane: ethyl acetate 3:1) and recrystallized in acetone to afford the pure
products 1 as colorless crystals. The results are shown in Tables 1, 2.
Table 2
Yields, mps and Elemental Analysis of 1b-f
Elemental Analysis (Found)
Yields mp
Cmpd
(%)
(◦C)
C
H
N
Formula (M.W.)
1b
1c
1d
1e
1f
86
90
87
87
85
125 62.15(62.12) 6.35(6.33) 6.30(6.32) C23H28N2O7 (444.48)
108 60.57(60.56) 5.81(5.82) 6.73(6.73) C21H24N2O7 (416.42)
112 62.15(62.13) 6.35(6.33) 6.30(6.31) C23H28N2O7 (444.48)
97 62.14(62.11) 5.96(5.93) 3.45(3.49) C21H24ClNO5 (405.87)
105 63.66(63.63) 6.50(6.47) 3.23(3.25) C23H28ClNO5 (433.93)

One-pot Synthesis of Some New Indene Derivatives
281
Table 3
Spectroscopic Data of 2a-f
Cmpd
1H NMR (δ:ppm)
13C NMR (δ:ppm)
MS (m/z)
416 (M+, 15)
2a
1.33–1.94 (10H, 4m, CH2 23.04, 23.72, 24.60, CH2
of cyclohexyl); 2.67 (3H, of cyclohexyl); 32.94
s, CH3); 3.68, 3.88 (6H,
2s, CH3 of CO2Me);
384 (M+-MeOH,16)
(CH3); 49.17 (C ipso of
cyclopentene); 61.56,
291 (M+-C6H11NCO, 95)
252 (M+-C6H11NCO,
CH3OH, 100)
3.78–3.80 (1H, m, CH of 63.08 (2 CH3 of
cyclohexyl); 7.61–7.62,
8.32–8.37 (1H, d, J =
8.35 Hz; 2H, m, Ar
CO2Me); 68.92(C of
cyclohexyl); 117.33,
123.00, 125.77, 137.22,
protons); 8.48–8.50 (1H, 144.15, 148.41, 151.23,
d, J = 0.65 Hz, NH).
152.49 (Alkene and Ar
carbons); 163.71, 164.09
(C O of CO2Me);
171.03(C O of amide).
2b
1.15–1.18 (3H, t, CH3 of, 13.04, 14.15 (CH3 of
444 (M+, 12)
CO2Et); 1.34–1.44,
1.75–1.93(13 H, 4m,
CH3 of CO2Et, CH2 of
CO2Et); 24.94, 25.97,
26.60 (CH2 of
cyclohexyl); 33.02
398 (M+-C2H5OH, 25)
319 (M+-C6H11NCO, 83)
273(M+-C6H11NCO,
C2H5OH, 100)
cyclohexyl); 2.66 (3H, s, (CH3); 49.17 (Cipso of
CH3); 3.7–3.78
(1H,m,CH of
cyclohexyl); 61.28, 63.08
(CH2 of CO2Et); 68.92
(CH of cyclohexyl);
118.06, 122.63, 125.32,
137.43, 143.74, 148.41,
151.50, 152.49 (Alkene
and Ar carbons); 163.73,
164.09 (2 C O of
cyclohexyl); 4.00–4.06,
4.26, 4.28(2H, 2m, CH2
of CO2Et); 4.28–4.34
(2H, q,CH2 of CO2Et);
7.30–7.61, 8.32–8.36
(3H, 2m, Ar protons);
8.56–8.57 (1H, d, J =
7.6 Hz, NH)
CO2Et); 170.75 (C O
of amide)
2c
1.23–1.82 (10H, 4m, CH2 23.23, 24.15, 24.71 (CH2 416 (M+, 13)
of cyclohexyl); 2.70 (3H, of cyclohexyl); 32.39
384 (M+-CH3OH, 23)
s, CH3); 3.40–3.96 (1H,
m, CH of cyclohexyl);
4.04–4.16 (6H, 2s, CH3
of CO2Me); 7.68–7.71,
8.33–8.58 (3H, 2m, Ar
protons); 8.60 (1H, d,
J = 7.1 Hz, NH)
(CH3); 50.56 (C ipso of
cyclopentene ring);
62.04, 63.15 (2 CH3 of
CO2Me); 69.12 (CH
ofcyclohexyl);
291 (M+-C6H11NCO, 80)
259 (M+-C6H11NCO,
CH3OH, 100)
120.56,123.93, 125.85,
135.19, 141.45, 146.30,
149.00, 149.74 (Alkene
and Ar cabons); 161.23,
162.70 (2 C O of
CO2Me); 171.03 (C O
of amide)
(Continued on next page)

282
Zonouzi et al.
Table 3
Spectroscopic Data of 2a-f (Continued)
Cmpd
1H NMR (δ:ppm)
13C NMR (δ:ppm)
MS (m/z)
2d
1.15–1.78 (3H, t, CH3 of 14.94, 15.98 (2 CH3 of
444 (M+, 11) 398
(M+-C2H5OH, 30)
CO2Et); 1.34–1.42,
1.75–1.93 (13H, 4m,
CH3 of CO2Et, CH2 of
cyclohexyl); 2.68(3H, s,
CH3); 3.75 (1H, m, CH
of cyclohexyl);
CO2Et); 23.04, 24.15,
24.60 (CH2 of cyclohexyl); 319 (M+- C6H11NCO, 78)
33.69 (CH3); 49.12 (Cipso 273 (M+-C6H11NCO,
of cyclopentene); 61.43,
63.63 (CH2 of CO2Et);
68.32 (CH of
C2H5OH, 100)
4.26–4.35 (4H, 2q, CH2
of CO2Et); 7.30–7.38,
7.60- 7.62, 8.33–8.38
(3H, 3m, Ar protons);
8.57–8.58 (1H, d, J =
7.55Hz, NH)
cyclohexyl);117.28,
123.08, 125.92, 141.06,
142.02, 149.41,152.13,
153.60 (Alkene and Ar
carbons); 163.23, 164.05
(2 C O of CO2Et); 171.08
(C O of amide)
2e
1.25–1.82 (10H, 4m, CH2 23.84, 24.49, 24.92 (CH2 of 405, 407 (M+, M++2, 40,
of cyclohexyl); 2.63
(3H, s, CH3); 3.96–3.99
(1 H, m, CH of
cyclohexyl); 33.24 (CH3);
50.06 (Cipso of
12)
373, 375 (M+,
cyclopentene ring);
M++2-CH3OH, 25, 6),
280, 282 (M+, M++2-
C6H11NCO, 85, 35)
248, 250 (M+,
cyclohexyl); 4.04, 4.15
(6H, 2s, CH3 of
CO2Me); 7.06–7.08,
7.13–7.17 (3H, 2m, Ar
protons); 8.56–8.57(1H,
d, J = 4.41Hz, NH)
62.13–63.49 (2 CH3 of
CO2Me); 69.08 (13CH of
cyclohexyl); 123.45,
126.02, 127.44, 128.44,
129.17, 132.43, 146.24,
148.12 (Alkene and Ar
carbons); 163.12, 164.39
(2 C O of CO2Me);
170.43 (C O of amide)
M++2-C6H11NCO,
CH3OH, 100, 40)
2f
1.15–1.18 (3H, t, CH3 of 14.32, 14.88 (2 CH3 of
432, 434 (M+, M++2, 25,8)
396, 398 (M+, M+
CO2Et); 1.34–1.42,
1.75–1.76, 1.77–1.93
(13H, 4m, CH3 of
CO2Et, CH2 of
CO2Et); 24.62, 25.91,
26.17 (CH2 of cyclohexyl); 2-C2H5OH, 35, 9)
33.13 (CH3); 49.08 (Cipso 307, 309 (M+, M+2-
of cyclopentene); 61.13,
63.48 (CH2 of CO2Et);
68.92 (CH of cyclohexyl);
122.63, 125.32, 127.47,
128.42, 129.47, 132.43,
146.74, 148.41 (Alkene
and Ar carbons); 163.19,
164.28 (2 C O of CO2Et);
171.15 (C O of amide)
C6H11NCO, 85, 30)
261, 263 (M+, M+2-
C6H11NCO, C2H3OH,
100, 39)
cyclohexyl); 2.66 (3H,
s, CH3); 4.03 (1H, m,
CH of cyclohexyl);
4.24–4.26, 4.26–4.29
(2H, 2m, CH2 of
CO2Et); 4.31–4.34 (2H,
q, CH2 of CO2Et);
7.06–7.07 (1H, d, J =
4.59Hz, Ar protons);
7.14–7.17 (2H, m, Ar
protons), 8.56–8.58
(1H, d, J = 9.15Hz,
NH)

One-pot Synthesis of Some New Indene Derivatives
283
Table 4
Yields, mps and Elemental Analysis of 2a-f
Elemental Analysis (Found)
mp
∗Yields
Cmpd (%)
(◦C)
C
H
N
Formula (M.W.)
2a
2b
2c
2d
2e
2f
87
85
88
86
85
83
134–135 60.57(60.55) 5.81(5.80) 6.73(6.74) C21H24N2O7 (416.42)
142–143 62.15(62.13) 6.35(6.32) 6.30(6.33) C23H28N2O7 (444.48)
131–132 60.57(60.58) 5.81(5.80) 6.73(6.75) C21H24N2O7 (416.42)
139–140 62.15(62.13) 6.35(6.35) 6.30(6.34) C23H28N2O7 (444.48)
121–122 62.14(62.12) 5.96(5.94) 3.45(3.48) C21H24ClNO5 (405.87)
128–129 63.66(63.65) 6.50(6.47) 3.23(3.24) C23H28ClNO5 (433.93)
∗Yields from one-pot procedure.
Acknowledgement
The support of this study by the Research Council at the University of Tehran is gratefully
acknowledged.
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