JOURNAL OF CHEMICAL RESEARCH 2017 405
Acknowledgment
s, OH), 6.87 (2 H, d, J = 7.6 Hz, 2 × ArH), 7.15 (2 H, d, J = 7.6 Hz, 2
ArH), 7.28 (1 H, t, J = 7.5 Hz, ArH), 7.67 (1 H, t, J = 7.5 Hz, ArH),
×
The authors gratefully acknowledge the support of the Research
Council of Islamic Azad University of Gorgan.
13
7.85 (1 H, d, J = 7.7 Hz, ArH), 7.96 (1 H, d, J= 7.7 Hz, ArH); C NMR
(
1
125.7 MHz, CDCl ) d 21.4 (Me), 28.9 (Me C), 58.3 (Me C), 94.4 (C),
3
3
3
03.4 (C), 123.7 (2 × CH), 127.2 (CH), 128.4 (CH), 129.3 (CH), 130.5
Received 25 January 2017 accepted 2 June 2017
Paper 1704570
(
(
2 × CH), 131.2 (C), 134.2 (C), 143.2 (CH), 148.3 (C), 149.5 (C), 163.6
C=N), 166.2 (C=O), 195.2 (C=O); EI–MS (%): 410 ([M] , 15), 325
+
(
68), 305 (86), 119 (100), 57 (100); Anal. calcd for C H N O S: C,
Published online: 30 June 2017
2
2
22
2
4
6
4.37; H, 5.40; N, 6.82; found: C, 64.48; H, 5.53; N, 6.93%.
-(4-Bromobenzoyl)-3a,8a-dihydroxy-2-(methylimino)-3a,8a-
dihydro-2H-indeno[1,2-d][1,3]-thiazol-8(3H)-one (5e): Yellow
3
References
−1
powder; yield 0.75 g, 87%; m.p. 183–185 °C; IR (ν /cm ) KBr:
1
CDCl ) d 3.22 (3 H, s, NMe), 4.15 (1 H, s, OH), 4.24 (1 H, s, OH), 7.12
(
H, d, J = 7.8 Hz, 2 × ArH), 7.68 (1 H, t, J = 7.6 Hz, ArH), 7.87 (1 H,
d, J = 7.6 Hz, ArH), 8.02 (1H, d, J = 7.6 Hz, ArH); C NMR (125.7
MHz, CDCl ) d 34.2 (NMe), 94.6 (C–O), 104.3 (C–O), 115.2 (C),
1
1
2
3
4
A. Domling, Chem. Rev., 2006, 106, 17.
max
1
736, 1725, 1695, 1643, 1587, 1425, 1364, 1248; H NMR (500 MHz,
L.F. Tietze and N.N. Rackelmann, Pure. Appl. Chem., 2004, 11, 1967.
A. Domling and I. Ugi, Angew. Chem. Int. Ed., 2000, 39, 3168.
J. Kolb, B. Beck, M. Almstetter, S. Heck, E. Herdtweck and A. Domling,
Mol. Divers., 2003, 6, 297.
3
2 H, d, J = 7.8 Hz, 2 × ArH), 7.26 (1 H, t, J = 7.6 Hz, ArH), 7.56 (2
5
6
A. Domling, I. Ugi and B. Werner, Molecules, 2003, 8, 53-66.
R.S. Bon, B.V. Vliet, N.E. Sprenkels, R.F. Schmitz, F.J.J. Kanter, C.V.
Stevens, M. Swart, F.M. Bickelhaupt, M.B. Groen and R.V.A. Orru, J. Org.
Chem., 2005, 70, 3542.
13
3
23.6 (2 × CH), 127.2 (CH), 127.6 (CH), 128.2 (CH), 129.2 (CH), 132.3
(
1
2 × CH), 135.3 (C), 143.4 (CH), 148.6 (C), 151.2 (C), 163.7 (C=N),
7
L. Banfi, A. Basso, G. Guanti, N. Kielland, C. Repeto, R. Riva and I. Ugi J.
Org. Chem., 2007, 72, 2151.
+
+
66.7 (C=O), 194.8 (C=O); EI–MS (%): 433 ([M + 2] , 10), 404 ([M] ,
1
3
0), 329 (46), 184 (100); Anal. calcd for C H BrN O S: C, 49.90; H,
8
9
C.V. Galliford and K.A. Scheidt, J. Org. Chem., 2007, 72, 1811.
P. T. Anastas; T. C. Williamson, Frontiers in green chemistry. In: Green
chemistry: frontiers in benign chemical syntheses and processes, eds P. T.
Anastas and T. C. Williamson. Oxford University Press, 1998, pp 1–26.
18
13
2
4
.02; N, 6.47; found: C, 50.02; H, 3.14; N, 6.58%.
-(4-Nitrobenzoyl)-3a,8a-dihydroxy-2-(methylimino)-3a,8a-
dihydro-2H-indeno[1,2-d][1,3]-thiazol-8(3H)-one (5f): Yellow
3
−1
10 G.W.V. Cave, C.L. Raston and J.L. Scott, Chem. Commun., 2001, 2159.
powder; yield 0.76 g, 95%; m.p. 186–188 °C; IR (ν /cm ) KBr:
max
1
1
R.A. Sheldon, Chem. Ind., 1997, 12.
M. Sabbaghan and Z. Hossaini, Comb. Chem. High. Throughput Screen.,
2012, 15, 745.
I. Yavari, M. Sabbaghan and Z. Hossaini, Synlett, 2008, 1153
I. Yavari, S. Seifi, Z. Hossaini, M. Sabbaghan and F. Shirgahi-Talari,
Monatsh. Chem., 2008, 139, 1479.
1
1738, 1726, 1697, 1676, 1583, 1436, 1384, 1234; H NMR (500 MHz,
12
CDCl ) d 3.24 (3 H, s, NMe), 4.16 (1 H, s, OH), 4.27 (1 H, s, OH),
3
7.16 (2 H, d, J = 8.0 Hz, 2 × ArH), 7.23 (1 H, t, J = 7.5 Hz, ArH), 7.68
13
(1 H, t, J = 7.6 Hz, ArH), 7.83 (1 H, d, J = 7.6 Hz, ArH), 7.96 (1 H, d,
14
13
J = 7.6 Hz, ArH), 8.26 (2 H, d, J = 8.0 Hz, 2 × ArH); C NMR (125.7
MHz, CDCl ) d34.5 (NMe), 93.7 (C–O), 102.8 (C–O), 123.2 (2 × CH),
15 M. Hosseini-Sarvari, H. Sharghi and S. Etemad, Helv. Chim. Acta, 2008,
91, 715.
3
1
26.4 (2 × CH), 127.6 (CH), 128.2 (CH), 129.3 (CH), 135.3 (C), 142.5
16
S. Paul, P. Bhattacharyya and A.R. Das, Tetrahedron Lett., 2011, 52, 4636.
(
(
C), 143.2 (CH), 149.2 (C), 157.4 (C), 163.8 (C=N), 167.3 (C=O), 195.2
C=O); EI–MS (%): 399 ([M] , 15), 294 (68), 150 (100); Anal. calcd
+
17 H.R. Shaterian and M. Mohammadnia, J. Mol. Liq., 2013, 177, 353.
18
P.M. Dewick, Essentials of organic chemistry: for students of pharmacy,
medicinal chemistry and biological chemistry, John Wiley & Sons Ltd.,
Chichester, 2006.
for C H N O S(399.38): C, 54.13; H, 3.28; N, 10.52; found: C, 54.24;
18
13
3
6
H, 3.38; N, 10.65%.
-(2,2-Dimethylpropanoyl)-3a,8a-dihydroxy-2-(methylimino)-
a,8a-dihydro-2H-indeno[1,2-d][1,3]-thiazol-8(3H)-one (5g): Yellow
3
19
R. Breslow, J. Am. Chem. Soc., 1958, 80, 3719.
3
2
0
S. Miwatashi, Y. Arikawa, E. Kotani, M. Miyamoto, K.I. Naruo, H. Kimura,
T. Tanaka, S. Asah and S. Ohkawa, J. Med. Chem., 2005, 48, 5966.
−1
crystals; yield 0.51 g, 76%; m.p. 137–139 °C; IR (ν /cm ) KBr: 1735,
max
1
1
728, 1697, 1548, 1467, 1325, 1219. H NMR (500 MHz, CDCl ) d 1.28
21 C. Papadopoulou, A. Geronikaki and D. Hadjipavlou-Litina, Il Farmaco,
2005, 60, 969.
3
(9 H, s, Me C), 3.23 (3 H, s, NMe), 4.12 (1 H, s, OH), 4.18 (1 H, s, OH),
3
7
.19 (1 H, t, J= 7.6 Hz, ArH), 7.72 (1 H, t, J= 7.6 Hz, ArH), 7.83 (1 H, d,
22 Y. Kumar, R. Green, K.Z. Borysko, D.S. Wise, L.L. Wotring and L.B.
Townsend, J. Med. Chem., 1993, 36, 3843.
13
J= 7.8 Hz, ArH), 7.96 (1 H, d, J= 7.8 Hz, ArH); C NMR (125.7 MHz,
CDCl ) d 29.8 (Me C), 34.2 (NMe), 51.6 (Me C), 94.6 (C–O), 101.5
2
3
R. Pereira, C. Gaudon, B. Iglesias, P. Germain, H. Gronemeyer and A.R. de
Lera, Bioorg. Med. Chem. Lett., 2006, 16, 49.
3
3
3
(
1
C–O), 127.3 (CH), 128.6 (CH), 129.5 (CH), 136.4 (C), 143.2 (CH),
49.3 (C), 162.4 (C=N), 166.4 (C=O), 194.3 (C=O); EI–MS (%): 334
2
4
Y. Tsurumi, H. Ueda, K. Hayashi, S. Takase, M. Nishikawa, S. Kiyoto and
M. Okuhara, J. Antibiot., 1995, 48, 1066.
+
(
[M] , 15), 249 (64), 57 (100); Anal. calcd for C H N O S: C, 57.47;
16 18 2 4
25 F.W. Bell, A.S. Cantrell, M. Hoberg, S.R. Jaskunas, N.G. Johansson, C.L.
Jordon, M.D. Kinnick, P. Lind, J.M. Morin, B. Oberg, J.A. Palkowitz, C.A.
Parrish, J. Pranc, H. Zhang and X.X. Zhou, J. Med. Chem., 1995, 38, 4929.
26 D.S. Millan, R.H. Prager, C. Brand and P.H. Hart, Tetrahedron, 2000, 56,
811.
H, 5.43; N, 8.38; found: C, 57.56; H, 5.55; N, 8.48%.
-(2,2-Dimethylpropanoyl)-3a,8a-dihydroxy-2-(ethylimino)-3a,8a-
dihydro-2H-indeno[1,2-d][1,3]-thiazol-8(3H)-one (5h): Yellow
3
−1
powder; yield 0.52 g, 75%; m.p. 142–144 °C; IR (ν /cm ) KBr: 1736,
max
1
1
726, 1693, 1584, 1467, 1368, 1295; H NMR (500 MHz, CDCl ) d 1.23
27 W.L. Wang, D.Y. Yao, M. Gu, M.Z. Fan, J.Y. Li, Y.C. Xing and F. Nan,
Bioorg. Med. Chem. Lett., 2005, 15, 5284.
3
(3 H, t, J = 7.5, Me), 1.32 (9 H, s, Me C), 3.52 (1 H, m, CH), 4.14 (1 H,
3
2
8
J.V. Metzger, Comprehensive heterocyclic chemistry, Eds. A.R. Katritzky
and C.W. Rees, Pergamon Press, Oxford, 1984, 6, 235.
s, OH), 4.23 (1 H, s, OH), 7.23 (1 H, t, J = 7.6 Hz, ArH), 7.74 (1 H, t,
J= 7.6 Hz, ArH), 7.85 (1 H, d, J= 7.7 Hz, ArH), 7.95 (1 H, d, J= 7.7 Hz,
ArH); C NMR (125.7 MHz, CDCl ) d 13.5 (Me), 29.7 (Me C), 40.2
2
3
9
0
A. Hantzsch and J.H. Weber, Ber. Dtsch. Chem. Ges., 1887, 20, 3118.
E. Aguilar and A.I. Meyers, Tetrahedron Lett., 1994, 35, 2473.
13
3
3
(
(
NCH ), 52.2 (Me C), 93.2 (C–O), 98.6 (C–O), 128.2 (CH), 128.8
CH), 130.2 (CH), 135.8 (C), 143.4 (CH), 149.5 (C), 162.5 (C=N),
2
3
31 M. Ochiai, Y. Nishi, S. Hashimoto, Y. Tsuchimoto and D.W. Chen, J. Org.
Chem., 2003, 68, 7887.
+
166.5 (C=O), 194.5 (C=O); EI–MS (%): 348 ([M] , 15), 263 (64), 57
32 A. Rezvanian, A. Alizadeh and L.G. Zhu, Synlett, 2012, 23, 2526.
(
100); Anal. calcd for C H N O S: C, 58.60; H, 5.79; N, 8.04; found:
33 Gh. Mohammadi Ziarani, N. Lashgari, F. Azimian, H.G. Kruger, P.
17
20
2
4
C, 58.72; H, 5.83; N. 8.14%.
Gholamzadeh, Arkivoc, 2015, (vi), 1.