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PAPER
1H NMR (CDCl3): = 2.48 (s, 6 H), 7.34 (d, 4 H, J = 8.01 Hz), 8.06
(d, 4 H, J = 8.13 Hz). 13C NMR (CDCl3): = 21.9, 126.2, 129.6,
130.6, 145.6, 162.6.
Chem. 1971, 49, 3348. (c) Shambhu, M. B.; Digenis, G. A.
J. Chem. Soc., Chem. Commun. 1974, 619. (d) Tamura, Y.;
Kirihara, M.; Sasho, M.; Akai, S.; Sekihachi, J.; Okunaka,
R.; Kita, Y. J. Chem. Soc., Chem. Commun. 1987, 1474.
(e) Holzapfel, C. W.; Pettit, G. R. J. Org. Chem. 1985, 50,
2323. (f) Fukuoka, S.; Takimoto, S.; Katsuki, T.;
Yamaguchi, M. Tetrahedron Lett. 1987, 28, 4711.
(g) Tamura, Y.; Kirihara, M.; Sekihachi, J.; Okunaka, R.;
Mohri, S.; Tsugoshi, T.; Akai, S.; Sasho, M.; Kita, Y.
Tetrahedron Lett. 1987, 28, 3971. (h) Bryson, T. A.; Roth,
G. A. Tetrahedron Lett. 1986, 27, 3689.
Anal. Calcd for C16H14O3: C, 75.57; H, 5.55. Found: C, 75.61; H,
5.62.
o-Chlorobenzoic Anhydride (14h)
Oil.
IR (KBr): 1790 (C=O), 1735 cm–1 (C=O).
1H NMR (CDCl3): = 7.49 (m, 2 H), 7.66 (d, 2 H, J = 7.96 Hz), 8.03
(d, 2 H, J = 7.83 Hz), 8.11 (s, 2 H).
(2) Fife, W. K.; Zhang, Z. Tetrahedron Lett. 1986, 27, 4937.
(3) Adduci, J. M.; Ramirez, R. S. Org. Prep. Proced. Int. 1970,
2, 321.
(4) (a) Rinderknecht, H.; Ma, V. Helv. Chim. Acta 1964, 47,
162. (b) Rinderknecht, H.; Gutein, M. Org. Syn. Coll. 5;
Wiley: New York, 1973, 822. (c) Remigiusz, K.; Juliatiek,
R.; Shahriar, M. J. Org. Chem. 1994, 59, 2913.
(5) (a) Mestres, R.; Palomo, C. Synthesis 1981, 218.
(b) Burton, S. G.; Kaye, P. T. Synth. Commun. 1989, 19,
3331.
(6) Keshavamurthy, K. S.; Vankar, Y. D.; Dhar, D. N. Synthesis
1982, 506.
(7) (a) Hata, T.; Tajima, K.; Mukaiyama, T. Bull. Chem. Soc.
Jpn. 1968, 41, 2746. (b) Chen, F. M. F.; Benoiton, N. L.
Synthesis 1979, 710.
(8) (a) Eglinton, G.; Jones, E. R. H.; Shaw, B. L.; Whiting, M.
C. J. Chem. Soc. 1954, 1860. (b) Edman, J. R.; Simmons, H.
E. J. Org. Chem. 1968, 33, 3808. (c) Newman, M. S.;
Togue, M. W. J. Org. Chem. 1971, 36, 1398. (d) Kita, Y.;
Akai, S.; Yoshigi, M.; Nakajima, Y.; Yasuda, H.; Tamura,
Y. Tetrahedron Lett. 1984, 25, 6027. (e) Kita, Y.; Akai, S.;
Ajimura, N.; Yoshigi, M.; Tsugoshi, T.; Yasuda, H.;
Tamura, Y. J. Org. Chem. 1986, 51, 4150.
13C NMR (CDCl3): = 128.7, 130.3, 130.4, 130.5, 134.8, 135.3,
160.9.
Anal. Calcd for C14H8Cl2O3: C, 56.98; H, 2.73. Found: C, 57.11; H,
2.84.
p-Phenylbenzoic Anhydride (14i)
Mp 138–140 °C.
IR (KBr): 1780 (C=O), 1720 cm-1 (C=O).
1H NMR (CDCl3): = 7.44 (d, 2 H, J = 5.0 Hz), 7.50 (t, 4 H,
J = 10.0, 5.0 Hz), 7.65 (d, 4 H, J = 10.0 Hz), 7.75 (d, 4 H, J = 10
Hz), 8.24 (d, 4 H, J = 10 Hz).
13C NMR (CDCl3): = 127.4, 127.6, 127.7, 128.6, 129.1, 131.2,
139.6, 147.4, 162.4.
Anal. Calcd for C26H18O3: C, 82.52; H, 4.79. Found: C, 82.61; H,
4.87.
Thianaphthene-2-carboxylic Anhydride (14j)
Mp 140–141 °C.
IR (KBr): 1770 (C=O), 1710 cm–1 (C=O).
1H NMR (CDCl3): = 7.49 (m, 2 H), 7.66 (d, 2 H, J = 8.0 Hz), 8.03
(d, 2 H, J = 7.8 Hz), 8.11 (s, 2 H).
13C NMR (CDCl3): = 122.9, 125.4, 126.1, 128.1, 131.6, 133.5,
138.5, 143.3, 157.3.
(9) Rambacher, P.; Make, S. Angew. Chem. 1968, 80, 487.
(10) Sandler, S. R.; Karo, W. Organic Functional Group
Preparations, Vol. 12; Academic Press: New York, 1972,
Chap. III.
(11) Blankemeyer-Menge, B.; Nimtz, M.; Frank, R. Tetrahedron
Lett. 1990, 31, 1701.
Anal. Calcd for C18H10S2O3: C, 63.89; H, 2.98; S, 18.95. Found: C,
63.93; H, 3.02; S, 19.01.
(12) Jorba, X.; Albericio, F.; Grandas, A.; Bannwarth, W.; Giralt,
E. Tetrahedron Lett. 1990, 31, 1915.
(13) (a) Katritzky, A. R.; Shobana, N.; Pernak, J.; Afridi, A. S.;
Fan, W.-Q. Tetrahedron 1992, 48, 7817. (b) Wakasugi, K.;
Nakamura, A.; Tanabe, Y. Tetrahedron Lett. 2001, 42,
7427. (c) Katritzky, A. R.; He, A. Y.; Suzuki, K. J. Org.
Chem. 2000, 65, 8210.
(14) Kweon, D. H.; Kim, H. K.; Kim, J. J.; Chung, H.-A.; Lee, W.
S.; Kim, S. K.; Yoon, Y. J. J. Heterocycl. Chem. 2002, 39,
203.
(15) Kang, Y. J.; Chung, H.-A.; Kim, J. J.; Yoon, Y. J. Synthesis
2002, 733.
(16) Compounds 10 and 11 were synthesized from saccharin and
2-pyridone, respectively, by reacting with 4-nitrobenzene-
sulfonyl chloride in the presence of Et3N in THF according
to Kweon’s Method.14
1-Benzoylbenzotriazole (12)
This compound was obtained from the reaction of benzoic acid (1)
with with the N-sulfonylheterocycle 9 (Table 2).
Mp 110–111 °C (Lit.18 mp 112–113 °C).
IR (KBr): 1720 cm–1 (C=O).
1H NMR (CDCl3): = 7.57 (m, 3 H), 7.69 (m, 2 H), 8.17 (d, 1 H,
J = 8.3 Hz), 8.22 (d, 2 H, J = 7.6 Hz), 8.40 (d, 1 H, J = 8.3 Hz).
13C NMR (CDCl3): = 114.8, 120.2, 126.4, 128.5, 130.4, 131.6,
131.8, 132.4, 133.7, 145.8, 166.8.
Acknowledgment
(17) The Merck Index; Merck & Co., Inc.: New Jersey, 1983, 10th
ed., 156.
(18) Katritzky, A. R.; Shobana, N.; Pernak, J.; Afridi, A. S.; Fan,
W.-Q. Tetrahedron 1992, 48, 7817.
This work was supported by grant No. 2000-1-12300-003-2 from
the Basic Research Program of the Korea Science & Engineering
Foundation.
(19) Pollock, J. A. R.; Stevens, R. Dictionary of Organic
Compounds, Vol. 3; Oxford University Press: Oxford, 1965,
1592.
(20) Kita, Y.; Akai, S.; Yoshigi, M.; Nagajima, Y.; Yasuda, H.;
Tamura, Y. Tetrahedron Lett. 1984, 25, 6027.
References:
(1) (a) Ogliaruso, M. A.; Wolfe, J. F. Synthesis of Carboxylic
Acids, Esters and Their Derivatives; Wiley: New York,
1991, 198–217. (b) Mariella, R. P.; Brown, K. H. Can. J.
Synthesis 2003, No. 10, 1517–1520 © Thieme Stuttgart · New York