Organic & Biomolecular Chemistry
Communication
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Many transition-metal-catalyzed systems for the synthesis
of N-heterocycles have been developed. For examples of
using aldehydes as the starting material, see:
6 For transition-metal-catalyzed synthesis of N-heterocycles
using amines as substrates, see: (a) M. Pizzetti, E. De Luca,
E. Petricci, A. Porcheddu and M. Taddei, Adv. Synth. Catal.,
2012, 354, 2453; (b) L. De Luca and A. Porcheddu,
Eur. J. Org. Chem., 2011, 5791; (c) T. B. Nguyen,
J. L. Bescont, L. Ermolenko and A. Al-Mourabit, Org. Lett.,
2013, 15, 6218.
(
a) R. J. Abdel-Jalil, H. M. Aldoqum, M. T. Ayoub and
W. Voelter, Heterocycles, 2005, 65, 2061; (b) C. Balakumar,
P. Lamba, D. P. Kishore, B. L. Narayana, K. V. Rao,
K. Rajwinder, A. R. Rao, B. Shireesha and B. Narsaiah,
Eur. J. Med. Chem., 2010, 45, 4904; (c) D. Zhan, T. Li,
H. Wei, W. Weng, K. Ghandic and Q. Zeng, RSC Adv., 2013,
7 T. B. Nguyen, L. Ermolenko and A. Al-Mourabit, Green
Chem., 2013, 15, 2713.
3
, 9325; (d) R. G. Mahesh and P. S. N. Reddy, Indian
J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 1998, 37, 689;
e) R. G. Mahesh and P. S. N. Reddy, Indian J. Chem., Sect.
B: Org. Chem. Incl. Med. Chem., 1997, 36, 166;
f) K. S. Deepthi, D. S. Reddy, P. P. Reddy and
8 Metal-free C–N bond cleavage of amines using sulfur as an
oxidizing agent to synthesize N-heterocycles represents an
attractive approach, whereas H S is generated. T. B. Nguyen,
2
L. Ermolenko, W. A. Dean and A. Al-Mourabit, Org. Lett.,
2012, 14, 5948.
(
(
P. S. N. Reddy, Indian J. Chem., Sect. B: Org. Chem. Incl.
Med. Chem., 2000, 39, 220; (g) D. Zhan, T. Li, X. Zhang,
C. Dai, H. Wei, Y. Zhang and Q. Zeng, Synth. Commun.,
9 For selected examples, see: (a) N. J. Turner, Chem. Rev.,
2011, 111, 4073; (b) A. Roglans, A. Pla-Quintana and
M. Moreno-Mañas, Chem. Rev., 2006, 106, 4622;
(c) M. Gandelman and D. Milstein, Chem. Commun.,
2000, 1603; (d) S. Guo, B. Qian, Y. Xie, C. Xia and
H. Huang, Org. Lett., 2011, 13, 522; (e) R. D. Patil and
S. Adimurthy, Adv. Synth. Catal., 2011, 353, 1695;
(f) Z. Ling, L. Yun, L. Liu, B. Wu and X. Fu, Chem.
Commun., 2013, 49, 4214.
2
013, 43, 2493; (h) J. G. Kettle, S. Brown, C. Crafter,
B. R. Davies, P. Dudley, G. Fairley, P. Faulder, S. Fillery,
H. Greenwood, J. Hawkins, M. James, K. Johnson,
C. D. Lane, M. Pass, J. H. Pink, H. Plant and
S. C. Cosuliche, J. Med. Chem., 2012, 55, 1261; For examples
of Ullmann-type N-arylation, see: (i) X. Liu, H. Fu, Y. Jiang
and Y. Zhao, Angew. Chem., Int. Ed., 2009, 48, 348; 10 According to the referees’ comments, peroxyacids are well
(
2
3
j) C. Wang, S. Li, H. Liu, Y. Jiang and H. Fu, J. Org. Chem.,
010, 75, 7936; (k) W. Xu and H. Fu, J. Org. Chem., 2011, 76,
846; (l) W. Xu, Y. B. Jin, H. X. Liu, Y. Y. Jiang and H. Fu,
known to oxidize tertiary amines to N-oxides, so the
oxidative cyclocondensation of o-aminobenzamide 1a with
tri-n-butylamine 2c was performed using m-cpba (3-chloro-
perbenzoic acid) as an oxidant instead of dioxygen. It was
found that this reaction took place smoothly and the
corresponding product 2-propylquinazolin-4(3H)-one 3c
was obtained in 93% yield.
Org. Lett., 2011, 13, 1274; (m) K. S. Devanga, R. Nagarajan
and N. Rajagopal, Org. Biomol. Chem., 2012, 10, 3417;
(
n) D. S. Yang, Y. Y. Wang, H. J. Yang, T. Liu and H. Fu, Adv.
Synth. Catal., 2012, 354, 477; (o) M. A. McGowan,
C. Z. McAvoy and S. L. Buchwald, Org. Lett., 2012, 14, 3800; 11 (a) J. P. Ferris, R. D. Gerwe and G. R. Gapski, J. Org. Chem.,
(
p) X. Zhang, D. Ye, H. Sun, D. Guo, J. Wang, H. Huang,
1968, 33, 3493; (b) J. C. Craig, N. Y. Mary and L. Wolf,
J. Org. Chem., 1964, 29, 2868; (c) P. A. Bather, J. R. L. Smith
and R. O. C. Norman, J. Chem. Soc., C, 1971, 3060;
(d) M. B. Smith and J. March, March’s Advanced Organic
Chemistry, John Wiley & Sons, Hoboken, New Jersey, 6th
edn, 2007; (e) Y. Li, L. Ma and Z. Li, Chin. J. Org. Chem.,
2013, 33, 704.
X. Zhang, H. Jiang and H. Liu, Green Chem., 2009, 11, 1881;
for examples of using alcohol as a starting material, see:
(
(
Biomol. Chem., 2012, 10, 240; (s) H. Hidemasa, Y. Ino,
H. Suzuki and Y. Yokoyama, J. Org. Chem., 2012, 77, 7046;
q) J. Zhou and J. Fang, J. Org. Chem., 2011, 76, 7730;
r) A. J. A. Watson, A. C. Maxwell and J. M. Williams, Org.
(
(
t) W. Ge, X. Zhu and Y. Wei, RSC Adv., 2013, 3, 10817; 12 Aldehydes were formed in the absence of the substrate 1
u) M. Sharif, J. Opalach, P. Langer, M. Bellerb and X. Wu, under similar reaction conditions. For example, in the pres-
ence of 20 mol% Ph P(O)OH, tri-n-octylamine and
RSC Adv., 2014, 4, 8; for CO insertion and intramolecular
cyclization, see: (v) B. Ma, Y. Wang, J. L. Peng and Q. Zhu,
J. Org. Chem., 2011, 76, 6362; (w) F. Zeng and H. Alper, Org.
Lett., 2010, 12, 3642; (x) F. Zeng and H. Aiper, Org. Lett.,
2
tribenzylamine could be readily oxidized by dioxygen and
the corresponding aldehydes were obtained in 56% and
50% yields, respectively.
2
2
2
010, 12, 1188; (y) Z. Y. Zheng and H. Alper, Org. Lett., 13 In the absence of Ph P(O)OH, the reaction of benzaldehyde
008, 10, 829; (z) M. Costa, N. Della Cà, B. Gabriele,
with o-aminobenzamide 1a took place smoothly under
similar reaction conditions and the product 2-phenylquina-
zolin-4(3H)-one was produced in 97% yield.
C. Massera, G. Salerno and M. Soliani, J. Org. Chem., 2004,
9, 2469.
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Org. Biomol. Chem., 2014, 12, 3802–3807 | 3807