G Model
CCLET 3266 1–5
G.M. Raghavendra et al. / Chinese Chemical Letters xxx (2015) xxx–xxx
5
[6] S.B. Mhaske, N.P. Argade, The chemistry of recently isolated naturally occurring 148
quinazolinone alkaloids, Tetrahedron 62 (2006) 9787–9826.
[7] T. Onaka, A general three-step synthesis of pyrrolidino[2,1-b]quinazolone alka- 150
loids via biogenetically patterned path, Tetrahedron Lett. 12 (1971) 4387–4390. 151
[8] A. Hamid, A. Elomri, A. Daich, Expedious and practical synthesis of the bioactive 152
alkaloidsrutaecarpine, euxylophoricine A, deoxyvasicinone and their heterocyclic 153
90
91
92
93
94
95
96
97
(entry 3). Further screening of appropriate oxidants indicated
that DDQ is superior to iodine, iron chloride (FeCl3), tert-butyl
hydroperoxide (TBHP) were less effective in this oxidative
dehydrogenation reaction. In the absence of DDQ, 2,3-dihydro-
quinazolinone-4(1H)-one was formed and the results are summa-
rized in Table 1.
149
homologues, Tetrahedron Lett. 47 (2006) 1777–1781.
[9] J.R. Sheu, Pharmacological effects of rutaecarpine, an alkaloid isolated from evodia 155
rutaecarpa, Cardiovasc. Drug Rev. 17 (1999) 237–245.
[10] J. Michel, Quinoline, quinazoline and acridone alkaloids, Nat. Prod. Rep. 21 (2004) 157
650–668.
154
156
158
The influence of various solvents on the synthesis of 2,3-
disubstituted quinazolinone 4d was studied in which ethyl acetate
was chosen as the appropriate solvent with consideration of yield
and the results are summarized in Table 1 (entry 4–10).
Under the established conditions, we evaluated the reactions of
anthranilic acids (1a–c), amine (2a–f), and aldehydes (3a–g). In all
cases, products were obtained in good yield at room temperature.
Finally, benzylic amines, allylamines, amino esters also underwent
the title reaction under equally mild conditions. Furthermore, we
found that the reaction showed good tolerance to the electronic
properties of the substituents on the benzene ring of aldehydes.
The target quinzolinones 4(a–p) were all formed in excellent
yields, regardless of whether the aldehyde containing electron-
withdrawing or electron-donating substituent’s (Table 2).
A possible mechanism of the coupling cyclization to get di-
substituted quinazolinones suggested in Scheme 4. The catalytic
98
99
[11] A.M. Al-Obaid, S.G. Abdel-Hamide, H.A. El-Kashef, et al., Substituted quinazolines, 159
part 3. Synthesis, in vitro antitumor activity and molecular modeling study of 160
certain 2-thieno-4(3H)-quinazolinone analogs, Eur. J. Med. Chem. 44 (2009) 161
100
101
102
103
104
105
106
107
108
109
110
111
2379–2391.
162
[12] A.S. El-Azab, M.A. Al-Omar, A.A. Abdel-Aziz, et al., Design, synthesis and biological 163
evaluation of novel quinazoline derivatives as potential antitumor agents: mo- 164
lecular docking study, Eur. J. Med. Chem. 45 (2010) 4188–4198.
165
[13] J.F. Wolfe, T.L. Rathman, M.C. Sleevi, J.A. Campbell, T.D. Greenwood, Synthesis and 166
anticonvulsant activity of some new 2-substituted 3-aryl-4(3H)-quinazolinones, 167
J. Med. Chem. 33 (1999) 161–166.
168
[14] K. Terashima, H. Shimamura, A. Kawase, et al., Studies on antiulcer agents. IV: 169
Antiulcer effects of 2-benzylthio-5,6,7,8-tetrahydro-4(3H)-quinazolinones and 170
related compounds, Chem. Pharm. Bull. 43 (1995) 2021–2023.
[15] J.B. Koepfli, J.F. Mead, J.A. Brockman Jr., An alkaloid with high antimalarial activity 172
from dichroa-febrifuga, J. Am. Chem. Soc. 69 (1947) 1837.
[16] S. Kobayashi, M. Ueno, R. Suzuki, H. Ishitani, Catalytic asymmetric synthesis of 174
febrifugine and isofebrifugine, Tetrahedron Lett. 40 (1999) 2175–2178.
171
173
175
[17] S.L. Cao, Y.P. Feng, Y.Y. Jiang, et al., Synthesis and in vitro antitumor activity of 176
4(3H)-quinazolinone derivatives with dithiocarbamate side chains, Bioorg. Med. 177
112 Q2 reaction involves the activation of anthranilic acid 1a by T3P
Chem. Lett. 15 (2005) 1915–1917.
178
113
114
115
116
117
118
119
120
121
followed by reaction with amine to give anthranilamide. The
second step in the probable mechanism of T3P catalyzed
condensation of anthranilamide with aldehyde to afford an
intermediate E, which generates an imine intermediate F. The
byproduct P,P0,P00-tripropyl triphosphonic acid C protonates imine
to give protonated imine G. The next step involves intramolecualr
cycloaddition to yield the key intermediate H, and the subsequent
dehydrogenation to give the final 2,3-dihydroquinazolin-4(1H)-
one 4g.
[18] M.A.G. Nagwa, H.G. Hanan, M.Y. Riham, A.E.S. Nehad, Synthesis and antitumor 179
activity of some 2,3-disubstituted quinazolin-4(3H)-ones and 4,6-disubstituted- 180
1,2,3,4-tetrahydroquinazolin-2H-ones, Eur. J. Med. Chem. 45 (2010) 6058–6067. 181
[19] C. Huang, Y. Fu, H. Fu, Y. Jiang, Y. Zhao, Highly efficient copper-catalyzed cascade 182
synthesis of quinazoline and quinazolinone derivatives, Chem. Commun. 46 183
(2008) 6333–6335.
[20] J.F. Liu, J. Lee, M.A. Dalton, et al., Microwave-assisted one-pot synthesis of 2,3- 185
disubstituted 3H-quinazolin-4-ones, Tetrahedron Lett. 46 (2005) 1241–1244.
184
186
[21] I.K. Kostakis, A. Elomri, E. Segunin, M. Iannelli, T. Besson, Rapid synthesis of 2,3- 187
disubstituted quinazolin-4-ones enhanced by microwave-assisted decomposi- 188
tion of formamide, Tetrahedron Lett. 48 (2007) 6609–6613.
189
[22] M. Adib, E. Sheikhi, H.R. Bijanzadeh, Benzyl halides, that are first oxidized to 190
aldehydes under mild Kornblum conditions, undergo a three-component reaction 191
with isatoic anhydride and primary amines to produce 4(3H)-quinazolinones in 192
122
4. Conclusion
excellent yields, Synlett 23 (2012) 85–88.
193
[23] A. Kumar, A.K. Bishnoi, Nanoparticle mediated organic synthesis (NAMO-synthe- 194
sis): CuI-NP catalyzed ligand free amidation of aryl halides, RSC Adv. 4 (2014) 195
123
124
125
126
127
128
In summary, we developed a T3P catalyzed novel and
straightforward methodology for the synthesis of 2,3-disubstitut-
ed quinazolinones by one-pot and three component reaction using
anthranilic acid. This method features short reaction time, broad
functional group tolerance, easy isolation, high yield and simple
procedure.
41631–41635.
196
[24] H. Wei, T. Li, Y. Zhou, L. Zhou, Q. Zeng, Copper-catalyzed domino synthesis of 197
quinazolin-4(3H)-ones from (hetero) arylmethyl halides, bromoacetate, and 198
cinnamyl bromide, Synthesis 45 (2013) 3349–3354.
[25] J. Zhou, L. Fu, M. Lv, et al., Copper(I) iodide catalyzed domino process to quina- 200
zolin-4(3H)-ones, Synthesis 24 (2008) 3974–3980.
[26] J. Raid, J.V. Wolfgang, S. Muhammad, A novel method for the synthesis of 4(3H)- 202
quinazolinones, Tetrahedron Lett. 45 (2004) 3475–3476.
199
201
203
129
Acknowledgment
[27] H.Wissmann,H.J.Kleiner,Newpeptidesynthesis,Angew. Chem. 92(1980)133–134. 204
[28] R. Escher, P. Bunning, Synthesis of N-(1-Carboxy-5-aminopentyl)dipeptides as 205
inhibitors of angiotensin converting enzyme, Angew. Chem. Int. Ed. 25 (1986) 206
130 Q3
Financial support from DST-Fast track, New Delhi (No. SERB/F/
2013-14) is gratefully acknowledged.
277–278.
207
131
ˆ1
[29] N. Basavaprabhu, R.S. Narendra, V.V. Lamani, Sureshbabu, T3PA (propylpho- 208
sphonic anhydride) mediated conversion of carboxylic acids into acid azides and 209
one-pot synthesis of ureidopeptides, Tetrahedron Lett. 51 (2010) 3002–3005.
210
132
Appendix A. Supplementary data
[30] B.S. Patil, G.R. Vasanthakumar, V.V. Sureshbabu, Isocyanates of N a-[(9-fluore- 211
nylmethyl)oxy]carbonyl amino acids: synthesis, isolation, characterization, and 212
application to the efficient synthesis of urea peptidomimetics, J. Org. Chem. 68 213
133
134
Supplementary data associated with this article can be found, in
(2003) 7274–7280.
214
[31] J.K. Augustine, A. Bombrun, A.B. Mandal, et al., Propylphosphonic anhydride 215
(T3P1)-mediated one-pot rearrangement of carboxylic acids to carbamates, 216
Synthesis 9 (2011) 1477–1483.
[32] M. Desroses, T. Koolmeister, S. Jacques, et al., A facile and efficient synthesis of 218
tetrahydro-b-carbolines, Tetrahedron Lett. 54 (2013) 3554–3557.
[33] T.M. Basavaprabhu, N.R. Vishwanatha, V.V. Panguluri, Sureshbabu, Propanepho- 220
sphonic acid anhydride (T3P1
– a benign reagent for diverse applications 221
inclusive of large-scale synthesis, Synthesis 45 (2013) 1569–1601.
217
135
References
219
136
137
138
139
140
141
142
143
144
145
146
147
[1] A. Do¨mling, Recent developments in isocyanide based multicomponent reactions
in applied chemistry, Chem. Rev. 106 (2006) 17–89.
[2] C. Hulme, V. Gore, Multi-component reactions: emerging chemistry in drug
discovery ‘From Xylocain to Crixivan’, Curr. Med. Chem. 10 (2003) 51–80.
[3] J. Zhu, Recent developments in the isonitrile-based multicomponent synthesis of
heterocycles, Eur. J. Org. Chem. (2003) 1133–1144.
[4] A. Do¨mling, I. Ugi, Multicomponent reactions with isocyanides, Angew. Chem. Int.
Ed. 39 (2000) 3168–3210.
[5] (a) L. Weber, High-diversity combinatorial libraries, Curr. Opin. Chem. Biol. 4
(2000) 295–302;
)
222
[34] G.M. Raghavendra, A.B. Ramesha, C.N. Revanna, et al., One-pot tandem approach 223
for the synthesis of benzimidazoles and benzothiazoles from alcohols, Tetrahe- 224
dron Lett. 52 (2011) 5571–5574.
225
[35] A.B. Ramesha, G.M. Raghavendra, K.N. Nandeesh, K.S. Rangappa, K. Mantelingu, 226
Tandem approach for the synthesis of imidazo[1,2-a]pyridines from alcohols, 227
Tetrahedron Lett. 54 (2013) 95–100.
228
[36] C.N. Revanna, G.M. Raghavendra, T.A. Jenifer Vijay, et al., Propylphosphonic 229
anhydride-catalyzed tandem approach for biginelli reaction starting from alco- 230
(b) A. Domling, Recent advances in isocyanide-based multicomponent chemistry,
Curr. Opin. Chem. Biol. 6 (2002) 306–313.
hols, Chem. Lett. 43 (2014) 178–180.
231
Please cite this article in press as: G.M. Raghavendra, et al., T3P catalyzed one pot three-component synthesis of 2,3-disubstituted 3H-