New Reactivities of Nitrogen-Containing Aromatics and Their Synthetic Application

This review describes new knowledge on reactivities and syntheses of N-containing aromatics and their application to the synthesis of natural products covering three subjects. 1) The first part describes the Fischer indole synthesis of o-substituted phenylhydrazones, its mechanism, Reissert indole s...

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Published inYAKUGAKU ZASSHI Vol. 122; no. 11; pp. 869 - 888
Main Author MURAKAMI, Yasuoki
Format Journal Article
LanguageJapanese
Published Japan The Pharmaceutical Society of Japan 01.11.2002
Subjects
Acylation
Aniline Compounds - chemical synthesis
Ar-N chirality
Catalysis
diacylanilines
Ergot Alkaloids - chemical synthesis
Fischer indole synthesis
indoles
Indoles - chemical synthesis
Nitrogen
Palladium
Pd-catalyzed reaction
Pyrroles
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Abstract This review describes new knowledge on reactivities and syntheses of N-containing aromatics and their application to the synthesis of natural products covering three subjects. 1) The first part describes the Fischer indole synthesis of o-substituted phenylhydrazones, its mechanism, Reissert indole synthesis, a new synthetic approach from pyrrole to indole, some reactions of indoles (i.e., etc.), acylation, bromination, debromination, debenzylation, Vilsmeier-Haack reaction, and synthesis of 4-methoxy-β-carboline alkaloids. 2) The second part describes a new method of introduction of allyl and vinyl groups on the indole nucleus by means of a Pd catalyst. This method was applied to the synthesis of optically active ergot alkaloids. 3) The third part describes the synthesis of o-substituted diacylanilines and its application to chemoselective acylating reagents. A study on axial chirality based on the Ar-N axis is also involved.
AbstractList This review describes new knowledge on reactivities and syntheses of N-containing aromatics and their application to the synthesis of natural products covering three subjects. 1) The first part describes the Fischer indole synthesis of o-substituted phenylhydrazones, its mechanism, Reissert indole synthesis, a new synthetic approach from pyrrole to indole, some reactions of indoles (i.e., etc.), acylation, bromination, debromination, debenzylation, Vilsmeier-Haack reaction, and synthesis of 4-methoxy-beta-carboline alkaloids. 2) The second part describes a new method of introduction of allyl and vinyl groups on the indole nucleus by means of a Pd catalyst. This method was applied to the synthesis of optically active ergot alkaloids. 3) The third part describes the synthesis of o-substituted diacylanilines and its application to chemoselective acylating reagents. A study on axial chirality based on the Ar-N axis is also involved.This review describes new knowledge on reactivities and syntheses of N-containing aromatics and their application to the synthesis of natural products covering three subjects. 1) The first part describes the Fischer indole synthesis of o-substituted phenylhydrazones, its mechanism, Reissert indole synthesis, a new synthetic approach from pyrrole to indole, some reactions of indoles (i.e., etc.), acylation, bromination, debromination, debenzylation, Vilsmeier-Haack reaction, and synthesis of 4-methoxy-beta-carboline alkaloids. 2) The second part describes a new method of introduction of allyl and vinyl groups on the indole nucleus by means of a Pd catalyst. This method was applied to the synthesis of optically active ergot alkaloids. 3) The third part describes the synthesis of o-substituted diacylanilines and its application to chemoselective acylating reagents. A study on axial chirality based on the Ar-N axis is also involved.
This review describes new knowledge on reactivities and syntheses of N-containing aromatics and their application to the synthesis of natural products covering three subjects. 1) The first part describes the Fischer indole synthesis of o-substituted phenylhydrazones, its mechanism, Reissert indole synthesis, a new synthetic approach from pyrrole to indole, some reactions of indoles (i.e., etc.), acylation, bromination, debromination, debenzylation, Vilsmeier-Haack reaction, and synthesis of 4-methoxy-β-carboline alkaloids. 2) The second part describes a new method of introduction of allyl and vinyl groups on the indole nucleus by means of a Pd catalyst. This method was applied to the synthesis of optically active ergot alkaloids. 3) The third part describes the synthesis of o-substituted diacylanilines and its application to chemoselective acylating reagents. A study on axial chirality based on the Ar-N axis is also involved.
This review describes new knowledge on reactivities and syntheses of N-containing aromatics and their application to the synthesis of natural products covering three subjects. 1) The first part describes the Fischer indole synthesis of o-substituted phenylhydrazones, its mechanism, Reissert indole synthesis, a new synthetic approach from pyrrole to indole, some reactions of indoles (i.e., etc.), acylation, bromination, debromination, debenzylation, Vilsmeier-Haack reaction, and synthesis of 4-methoxy-beta-carboline alkaloids. 2) The second part describes a new method of introduction of allyl and vinyl groups on the indole nucleus by means of a Pd catalyst. This method was applied to the synthesis of optically active ergot alkaloids. 3) The third part describes the synthesis of o-substituted diacylanilines and its application to chemoselective acylating reagents. A study on axial chirality based on the Ar-N axis is also involved.
Author MURAKAMI, Yasuoki
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References 12) Murakami Y., Yokoo H., Yokoyama Y., Watanabe T., Chem. Pharm. Bull., 47, 791-797 (1999).
22) Suzuki H., Furukawa T., Yamada C., Shibuya I., Kurumi M., Yokoyama T., Murakami Y., Heterocycles, 56, 519-524 (2002).
52) Floss H. G., Tetrahedron, 32, 873-912 (1976).
46) Yokoyama Y., Takahashi M., Matsushima H., Kohno Y., Takashima M., Shidori K., Murakami., Advances in Tryptophan Research, 1992, 235-238.
53) Yokoyama Y., Matsumoto T., Murakami Y., J. Org. Chem., 60, 1486-1487 (1995).
8) Ishii H., Takeda H., Hagiwara T., Sakamoto M., Kogusuri K., Murakami Y., J. Chem. Soc., Perkin Trans.1, 1989, 2407-2414.
45) Murakami Y., Yokoyama Y., Aoki T., Heterocycles, 22, 1493-1496 (1984).
64) Kondo K., Murakami Y., Chem. Pharm. Bull., 46, 1217-1219 (1998).
59) Kondo K., Murakami Y., unpublished data.
32) Yokoyama Y., Okuyama N., Iwadate S., Momoi.T., Murakami Y., J. Chem. Soc., Perkin Trans. I, 1990, 1319-1329.
30) Suzuki H., Tsukuda A., Kondo M., Aizawa M., Senoo Y., Nakajima M., Watanabe T., Yokoyama Y., Murakami Y., Tetrahedron Lett., 36, 1671-1672 (1995).
40) Suzuki, Murakami: unpublished data.
10) Miyata O., Muroya K., Hiramatsu H., Naito T., Tetrahedron Lett., 40, 3601-3604 (1999).
24) Tani M., Matsumoto S., Aida Y., Arisawa S., Nakane A., Yokoyama Y., Murakami Y., Chem. Pharm. Bull., 42, 443-453 (1994).
71) Kondo K., Fujita H., Suzuki T., Murakami Y., Enantiomer, 5, 115-118 (2000).
58) Sudborough J. J., J. Chem. Soc., 1901, 533-541.
67) Kondo K., Kurosaki T., Murakami Y., Synlett., 1998, 725-726.
31) Murakami Y., Ishii H., Chem. Pharm. Bull., 29, 699-710 (1981).
50) Yokoyama Y., Takahashi M., Higaki C., Shidori K., Moriguchi S., Ando C., Murakami Y., Heterocycles, 35, 1739-1742 (1993).
18) Murakami Y., Watanabe T., Sakai M., Yokoyama Y., Chem. Pharm. Bull., 36, 3732-3735 (1988).
13) Noland W. E., Baude F. J., Org. Synth., Coll. Vol. V, 567-571 (1973).
57) Murakami Y., Watanabe T., Hagiwara T., Akiyama Y., Ishii H., Chem. Pharm. Bull., 43, 1281-1286 (1995).
3) Ishii H., Murakami Y., Hosoya K., Takeda H., Suzuki Y., Ikeda N., Tetrahedron, 29, 1991-2003 (1973).
70) Kitagawa O., Izawa H., Sato K., Dobashi A., Taguchi T., J. Org. Chem., 63, 2634-2640 (1998).
27) Tani M., Goto M., Shimizu M., Mochizuki Y., Amemiya J., Mizuno N., Sato R., Murakami Y., Synlett, 1996, 931-932.
55) Yokoyama Y., Kondo K., Mitsuhashi M., Murakami Y., Tetrahedron Lett., 37, 9309-9312 (1996).
33) Murakami Y., Yokoyama Y., Miura T., Nozawa S., Takeda E., Suzuki H., Heterocycles, 27, 2341-2344 (1988).
35) Murakami Y., Yokoyama Y., Aoki C., Suzuki H., Sakurai K., Shinohara T., Miyagi C., Kimura Y., Takahashi T., Watanabe T., Ohnoto T., Chem. Pharm. Bull., 39, 2189-2195 (1991).
29) Watanabe T., Kobayashi. A, Nishiura M., Takahashi H., Usui T., Kamiyama I., Mochizuki N., Noritake K., Yokoyama Y., Murakami Y., Chem. Pharm. Bull., 39, 1152-1156 (1991).
39) Suzuki H., Unemoto M., Hagiwara M., Ohyama T., Yokoyama Y., Murakami Y., J. Chem.Soc., Perkin Trans. 1, 1999, 1717-1723.
62) Atkinson R. S., Barker E., Sutcliffe M., J. Chem. Soc., Chem. Commun., 1996, 1051-1052.
36) Suzuki H., Iwata C., Sakurai K., Tokumoto K., Takahashi H., Hanada M., Yokoyama Y., Murakami Y., Tetrahedron, 53, 1593-1606 (1997).
11) Miyata O., Kimura Y., Naito T., Chem. Commun., 1999, 2429-2430.
56) Osanai K., Yokoyama Y., Kondo K., Murakami Y., Chem. Pharm. Bull., 47, 1587-1590 (1999).
7) Robinson B., "The Fischer Indole Synthesis," John Wiley & Sons (1982).
1) Ishii H., Murakami Y., Suzuki Y., Ikeda N., Tetrahedron Lett., 1970, 1181-1184.
21) Tani M., Aoki T., Ito S., Matsumoto S., Hidesima M., Fukushima K., Nozawa R., Maeda T., Mashiro M., Yokoyama Y., Murakami Y., Chem. Pharm. Bull., 38, 3261-3267 (1990).
25) Kruse L. I., Meyer M. D., J. Org. Chem., 49, 4761-4768 (1984).
37) Suzuki H., Miyagi C., Yokoyama Y., Murakami Y., Chem. Pharm. Bull., 39, 2170-2172 (1991).
60) Kunieda T., Higuchi T., Abe Y., Hirobe M., Tetrahedron Lett., 23, 1159-1160 (1982).
6) Murakami Y., Yokoo H., Watanabe T., Heterocycles, 49, 127-132 (1998).
51) Heck R. F., "Organic Reaction," Vol. 27, ed. by Dauben W. G., John Wiley and Sons. Inc., New York, 1982, pp. 345-390.
23) Yokoyama Y., Uchida M., Murakami Y., Heterocycles, 29, 1661-1662 (1989).
4) Murakami Y., Watanabe T., Yokoyama Y., Naomachi J., Iwase H., Watanabe N., Morihata M., Okuyama N., Kamakura H., Takahashi T., Atoda H., Tojo T., Morita K., Ishii H., Chem. Pharm. Bull., 41, 1910-1919 (1993).
17) Watanabe T., Miyagi C., Murakami Y., J. Heterocyclic Chem., 30, 217-224 (1993).
9) Suzuki H., Tukakosi Y., Tatikawa T., Murakami Y., 反応と合成の進歩シンポジウム, p42, 2001, 仙台.
26) Tani M., Ikegami H., Tashiro M., Hiura T., Tsukioka H., Kaneko C., Notoya T., Shimizu M., Uchida M., Aida Y., Yokoyama Y., Murakami Y., Heterocycles, 34, 2349-2362 (1992).
49) Harrington P. J., Hegedus L. S., McDaniel K. F., J. Am. Chem. Soc., 109, 4335-4338 (1987).
15) Tani M., Ariyasu T., Nishiyama C., Hagiwara H., Watanabe T., Yokoyama Y., Murakami Y., Chem. Pharm. Bull., 44, 48-54 (1996).
63) Murakami Y., Kondo K., Miki K., Akiyama Y., Watanabe T., Yokoyama Y., Tetrahedron Lett., 38, 3751-3754 (1997).
16) Murakami Y., Watanabe T., Ishii H., J. Chem. Soc., Perkin Trans. 1, 1988, 3005-3012.
66) Kondo K., Sekimoto E., Nakao J., Murakami Y., Tetrahedron, 56, 5843-5856 (2000).
28) Murakami Y., Watanabe T., Kobayashi A., Yokoyama Y., Synthesis, 1984, 738-740.
61) Kikugawa Y., Mitsui K., Sakamoto T., Kawase M., Tamiya H., Tetrahedron Lett., 31, 243-246 (1990).
14) Suzuki H., Gyoutoku H., Yokoo H., Shinba M., Sato Y., Synlett, 2000, 1196-1198.
48) Yokoyama Y., Takahashi M., Kohno Y., Kataoka K., Fujikawa Y., Murakami Y., Heterocycles, 31, 803-804 (1990).
5) Murakami Y., Watanabe T., Takahashi H., Yokoo H., Nakazawa Y., Koshimizu M., Adachi N., Kurita M., Yoshino T., Inagaki T., Ohishi M., Tetrahedron, 54, 45-64 (1998).
65) Kondo K., Sekimoto E., Miki K., Murakami Y., J. Chem. Soc., Perkin Trans. 1, 1998, 2973-2974.
69) Kurran D. P., Qi H., Guib S. J., DeMello N. C., J. Am. Chem. Soc., 116, 3131-3132 (1994).
34) Cain M., Mantei R., Cook J. M., J. Org. Chem., 47, 4933-4936 (1982).
47) Yokoyama Y., Takahashi M., Matsushima M., Kohno Y., Kobayashi H., Kataoka K., Shidori K., Murakami Y., Chem. Pharm. Bull., 42, 832-838 (1994).
41) Pigulla J., Röder E., Liebigs Ann. Chem., 1978, 1390-1398.
43) Yokoyama Y., Ito S., Takahashi Y., Murakami Y., Tetrahedron Lett., 26, 6457-6460 (1990).
20) Murakami Y., Tani M., Tanaka K., Yokoyama Y., Chem. Pharm. Bull., 36, 2023-2035 (1988).
68) Kondo K., Fujita H., Suzuki T., Murakami Y., Tetrahedron Lett., 40, 5577-5580 (1999).
44) Yokoyama Y., Ikeda M., Sato M., Yoda T., Suzuki H., Murakami Y., Heterocycles, 31, 1505-1511 (1990).
19) Murakami Y., Tani M., Zuzuki M., Sudoh K., Uesato M., Tanaka K., Yokoyama Y., Chem. Pharm. Bull., 33, 4707-4716 (1985).
38) Suzuki H., Ebihara Y., Yokoyama Y., Murakami Y., Heterocycles, 46, 57-60 (1997).
54) Hikawa H., Yokoyama Y., Murakami Y., Synthesis, 2000, 214-216.
42) Suzuki H., Shinpo K., Yamazaki T., Niwa S., Yokoyama Y., Murakami Y., Heterocycles, 42, 83-86 (1996).
72) Kondo K., Iida T., Fujita H., Suzuki T., Yamaguchi K., Murakami Y., Tetrahedron, 56, 8883-8891 (2000).
2) Ishii H., Murakami Y., Hosoya K., Takeda H., Suzuki Y., Ikeda N., Chem. Pharm. Bull., 21, 1481-1494 (1973).
References_xml – reference: 6) Murakami Y., Yokoo H., Watanabe T., Heterocycles, 49, 127-132 (1998).
– reference: 18) Murakami Y., Watanabe T., Sakai M., Yokoyama Y., Chem. Pharm. Bull., 36, 3732-3735 (1988).
– reference: 41) Pigulla J., Röder E., Liebigs Ann. Chem., 1978, 1390-1398.
– reference: 27) Tani M., Goto M., Shimizu M., Mochizuki Y., Amemiya J., Mizuno N., Sato R., Murakami Y., Synlett, 1996, 931-932.
– reference: 8) Ishii H., Takeda H., Hagiwara T., Sakamoto M., Kogusuri K., Murakami Y., J. Chem. Soc., Perkin Trans.1, 1989, 2407-2414.
– reference: 59) Kondo K., Murakami Y., unpublished data.
– reference: 70) Kitagawa O., Izawa H., Sato K., Dobashi A., Taguchi T., J. Org. Chem., 63, 2634-2640 (1998).
– reference: 24) Tani M., Matsumoto S., Aida Y., Arisawa S., Nakane A., Yokoyama Y., Murakami Y., Chem. Pharm. Bull., 42, 443-453 (1994).
– reference: 48) Yokoyama Y., Takahashi M., Kohno Y., Kataoka K., Fujikawa Y., Murakami Y., Heterocycles, 31, 803-804 (1990).
– reference: 50) Yokoyama Y., Takahashi M., Higaki C., Shidori K., Moriguchi S., Ando C., Murakami Y., Heterocycles, 35, 1739-1742 (1993).
– reference: 26) Tani M., Ikegami H., Tashiro M., Hiura T., Tsukioka H., Kaneko C., Notoya T., Shimizu M., Uchida M., Aida Y., Yokoyama Y., Murakami Y., Heterocycles, 34, 2349-2362 (1992).
– reference: 55) Yokoyama Y., Kondo K., Mitsuhashi M., Murakami Y., Tetrahedron Lett., 37, 9309-9312 (1996).
– reference: 15) Tani M., Ariyasu T., Nishiyama C., Hagiwara H., Watanabe T., Yokoyama Y., Murakami Y., Chem. Pharm. Bull., 44, 48-54 (1996).
– reference: 61) Kikugawa Y., Mitsui K., Sakamoto T., Kawase M., Tamiya H., Tetrahedron Lett., 31, 243-246 (1990).
– reference: 65) Kondo K., Sekimoto E., Miki K., Murakami Y., J. Chem. Soc., Perkin Trans. 1, 1998, 2973-2974.
– reference: 67) Kondo K., Kurosaki T., Murakami Y., Synlett., 1998, 725-726.
– reference: 12) Murakami Y., Yokoo H., Yokoyama Y., Watanabe T., Chem. Pharm. Bull., 47, 791-797 (1999).
– reference: 28) Murakami Y., Watanabe T., Kobayashi A., Yokoyama Y., Synthesis, 1984, 738-740.
– reference: 53) Yokoyama Y., Matsumoto T., Murakami Y., J. Org. Chem., 60, 1486-1487 (1995).
– reference: 17) Watanabe T., Miyagi C., Murakami Y., J. Heterocyclic Chem., 30, 217-224 (1993).
– reference: 62) Atkinson R. S., Barker E., Sutcliffe M., J. Chem. Soc., Chem. Commun., 1996, 1051-1052.
– reference: 46) Yokoyama Y., Takahashi M., Matsushima H., Kohno Y., Takashima M., Shidori K., Murakami., Advances in Tryptophan Research, 1992, 235-238.
– reference: 52) Floss H. G., Tetrahedron, 32, 873-912 (1976).
– reference: 29) Watanabe T., Kobayashi. A, Nishiura M., Takahashi H., Usui T., Kamiyama I., Mochizuki N., Noritake K., Yokoyama Y., Murakami Y., Chem. Pharm. Bull., 39, 1152-1156 (1991).
– reference: 43) Yokoyama Y., Ito S., Takahashi Y., Murakami Y., Tetrahedron Lett., 26, 6457-6460 (1990).
– reference: 44) Yokoyama Y., Ikeda M., Sato M., Yoda T., Suzuki H., Murakami Y., Heterocycles, 31, 1505-1511 (1990).
– reference: 35) Murakami Y., Yokoyama Y., Aoki C., Suzuki H., Sakurai K., Shinohara T., Miyagi C., Kimura Y., Takahashi T., Watanabe T., Ohnoto T., Chem. Pharm. Bull., 39, 2189-2195 (1991).
– reference: 14) Suzuki H., Gyoutoku H., Yokoo H., Shinba M., Sato Y., Synlett, 2000, 1196-1198.
– reference: 37) Suzuki H., Miyagi C., Yokoyama Y., Murakami Y., Chem. Pharm. Bull., 39, 2170-2172 (1991).
– reference: 42) Suzuki H., Shinpo K., Yamazaki T., Niwa S., Yokoyama Y., Murakami Y., Heterocycles, 42, 83-86 (1996).
– reference: 72) Kondo K., Iida T., Fujita H., Suzuki T., Yamaguchi K., Murakami Y., Tetrahedron, 56, 8883-8891 (2000).
– reference: 66) Kondo K., Sekimoto E., Nakao J., Murakami Y., Tetrahedron, 56, 5843-5856 (2000).
– reference: 21) Tani M., Aoki T., Ito S., Matsumoto S., Hidesima M., Fukushima K., Nozawa R., Maeda T., Mashiro M., Yokoyama Y., Murakami Y., Chem. Pharm. Bull., 38, 3261-3267 (1990).
– reference: 13) Noland W. E., Baude F. J., Org. Synth., Coll. Vol. V, 567-571 (1973).
– reference: 68) Kondo K., Fujita H., Suzuki T., Murakami Y., Tetrahedron Lett., 40, 5577-5580 (1999).
– reference: 31) Murakami Y., Ishii H., Chem. Pharm. Bull., 29, 699-710 (1981).
– reference: 11) Miyata O., Kimura Y., Naito T., Chem. Commun., 1999, 2429-2430.
– reference: 45) Murakami Y., Yokoyama Y., Aoki T., Heterocycles, 22, 1493-1496 (1984).
– reference: 30) Suzuki H., Tsukuda A., Kondo M., Aizawa M., Senoo Y., Nakajima M., Watanabe T., Yokoyama Y., Murakami Y., Tetrahedron Lett., 36, 1671-1672 (1995).
– reference: 71) Kondo K., Fujita H., Suzuki T., Murakami Y., Enantiomer, 5, 115-118 (2000).
– reference: 19) Murakami Y., Tani M., Zuzuki M., Sudoh K., Uesato M., Tanaka K., Yokoyama Y., Chem. Pharm. Bull., 33, 4707-4716 (1985).
– reference: 4) Murakami Y., Watanabe T., Yokoyama Y., Naomachi J., Iwase H., Watanabe N., Morihata M., Okuyama N., Kamakura H., Takahashi T., Atoda H., Tojo T., Morita K., Ishii H., Chem. Pharm. Bull., 41, 1910-1919 (1993).
– reference: 40) Suzuki, Murakami: unpublished data.
– reference: 47) Yokoyama Y., Takahashi M., Matsushima M., Kohno Y., Kobayashi H., Kataoka K., Shidori K., Murakami Y., Chem. Pharm. Bull., 42, 832-838 (1994).
– reference: 54) Hikawa H., Yokoyama Y., Murakami Y., Synthesis, 2000, 214-216.
– reference: 3) Ishii H., Murakami Y., Hosoya K., Takeda H., Suzuki Y., Ikeda N., Tetrahedron, 29, 1991-2003 (1973).
– reference: 63) Murakami Y., Kondo K., Miki K., Akiyama Y., Watanabe T., Yokoyama Y., Tetrahedron Lett., 38, 3751-3754 (1997).
– reference: 5) Murakami Y., Watanabe T., Takahashi H., Yokoo H., Nakazawa Y., Koshimizu M., Adachi N., Kurita M., Yoshino T., Inagaki T., Ohishi M., Tetrahedron, 54, 45-64 (1998).
– reference: 23) Yokoyama Y., Uchida M., Murakami Y., Heterocycles, 29, 1661-1662 (1989).
– reference: 32) Yokoyama Y., Okuyama N., Iwadate S., Momoi.T., Murakami Y., J. Chem. Soc., Perkin Trans. I, 1990, 1319-1329.
– reference: 39) Suzuki H., Unemoto M., Hagiwara M., Ohyama T., Yokoyama Y., Murakami Y., J. Chem.Soc., Perkin Trans. 1, 1999, 1717-1723.
– reference: 56) Osanai K., Yokoyama Y., Kondo K., Murakami Y., Chem. Pharm. Bull., 47, 1587-1590 (1999).
– reference: 64) Kondo K., Murakami Y., Chem. Pharm. Bull., 46, 1217-1219 (1998).
– reference: 22) Suzuki H., Furukawa T., Yamada C., Shibuya I., Kurumi M., Yokoyama T., Murakami Y., Heterocycles, 56, 519-524 (2002).
– reference: 34) Cain M., Mantei R., Cook J. M., J. Org. Chem., 47, 4933-4936 (1982).
– reference: 51) Heck R. F., "Organic Reaction," Vol. 27, ed. by Dauben W. G., John Wiley and Sons. Inc., New York, 1982, pp. 345-390.
– reference: 60) Kunieda T., Higuchi T., Abe Y., Hirobe M., Tetrahedron Lett., 23, 1159-1160 (1982).
– reference: 58) Sudborough J. J., J. Chem. Soc., 1901, 533-541.
– reference: 69) Kurran D. P., Qi H., Guib S. J., DeMello N. C., J. Am. Chem. Soc., 116, 3131-3132 (1994).
– reference: 38) Suzuki H., Ebihara Y., Yokoyama Y., Murakami Y., Heterocycles, 46, 57-60 (1997).
– reference: 20) Murakami Y., Tani M., Tanaka K., Yokoyama Y., Chem. Pharm. Bull., 36, 2023-2035 (1988).
– reference: 16) Murakami Y., Watanabe T., Ishii H., J. Chem. Soc., Perkin Trans. 1, 1988, 3005-3012.
– reference: 2) Ishii H., Murakami Y., Hosoya K., Takeda H., Suzuki Y., Ikeda N., Chem. Pharm. Bull., 21, 1481-1494 (1973).
– reference: 7) Robinson B., "The Fischer Indole Synthesis," John Wiley & Sons (1982).
– reference: 49) Harrington P. J., Hegedus L. S., McDaniel K. F., J. Am. Chem. Soc., 109, 4335-4338 (1987).
– reference: 1) Ishii H., Murakami Y., Suzuki Y., Ikeda N., Tetrahedron Lett., 1970, 1181-1184.
– reference: 36) Suzuki H., Iwata C., Sakurai K., Tokumoto K., Takahashi H., Hanada M., Yokoyama Y., Murakami Y., Tetrahedron, 53, 1593-1606 (1997).
– reference: 25) Kruse L. I., Meyer M. D., J. Org. Chem., 49, 4761-4768 (1984).
– reference: 10) Miyata O., Muroya K., Hiramatsu H., Naito T., Tetrahedron Lett., 40, 3601-3604 (1999).
– reference: 57) Murakami Y., Watanabe T., Hagiwara T., Akiyama Y., Ishii H., Chem. Pharm. Bull., 43, 1281-1286 (1995).
– reference: 9) Suzuki H., Tukakosi Y., Tatikawa T., Murakami Y., 反応と合成の進歩シンポジウム, p42, 2001, 仙台.
– reference: 33) Murakami Y., Yokoyama Y., Miura T., Nozawa S., Takeda E., Suzuki H., Heterocycles, 27, 2341-2344 (1988).
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Snippet This review describes new knowledge on reactivities and syntheses of N-containing aromatics and their application to the synthesis of natural products covering...
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SubjectTerms Acylation
Aniline Compounds - chemical synthesis
Ar-N chirality
Catalysis
diacylanilines
Ergot Alkaloids - chemical synthesis
Fischer indole synthesis
indoles
Indoles - chemical synthesis
Nitrogen
Palladium
Pd-catalyzed reaction
Pyrroles
Title New Reactivities of Nitrogen-Containing Aromatics and Their Synthetic Application
URI https://www.jstage.jst.go.jp/article/yakushi/122/11/122_11_869/_article/-char/en
https://www.ncbi.nlm.nih.gov/pubmed/12440147
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Volume 122
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