1,4-Benzothiazines, Dihydro-1,4-benzothiazines, and Related Compounds.

Advances in Heterocyclic Chemistry

Volumn 38, Issue C, 1985, Pages 135-176

  Brown, C ^a   Davidson, R M ^a  

^a UNIVERSITY OF KENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001149063     PISSN: 00652725     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0065-2725(08)60919-8     Document Type: Article

References (209)

1. Szabo, J., Khim. Geterosikl. Soedin., 1979, 291.
2. [CA, 91, 1979, 39354.
3. Catsoulacos, P., Camoutsis, C., J. Heterocycl. Chem., 16, 1979, 1503.
4. Lombardino, J.G., Kuhla, D.E., Adv. Heterocycl. Chem., 28, 1981, 73.
5. Salisbury, M., Coffey, S., (eds.), 2nd ed. “Road's Chemistry of Carbon Compounds”, IVH, 1978, Elsevier, Amsterdam, 509.
6. Prota, G., “Organic Chemistry of Sulphur, Selenium and Tellurium”, 1, 1970, Chemical Society, London, 454 (Specialist Periodical Reports).
7. Prota, G., “Organic Chemistry of Sulphur, Selenium and Tellurium”, 2, 1973, Chemical Society, London, 758 (Specialist Periodical Reports).
8. Prota, G., “Organic Chemistry of Sulphur, Selenium and Tellurium”, 3, 1975, Chemical Society, London, 708 (Specialist Periodical Reports).
9. Prota, G., “Organic Chemistry of Sulphur, Selenium and Tellurium”, 4, 1977, Chemical Society, London, 453 (Specialist Periodical Reports).
10. Piechaczek, J., Wiad. Chem., 20, 1966, 233.
11. [CA, 65, 1966, 3864.
12. Chioccara, F., Prota, G., Thomson, R.H., Tetrahedron, 32, 1976, 1407.
13. Unger, O., Ber. Dtsch. Chem. Ges., 30, 1897, 607.
14. Friedrich, W., Kröhnke, F., Schiller, P., Chem. Ber., 98, 1965, 3804.
15. Bottex, P., Sillion, B., de Gaudemaris, G., Basselier, J.-J., C. R. Hebd. Acad. Sci., Seances Ser. C, 267, 1968, 186.
16. Wilhelm, M., Schmidt, P., J. Heterocycl. Chem., 6, 1969, 635.
17. MacKenzie, N.E., Thomson, R.H., Greenhalgh, C.W., J.C.S. Perkin I, 1980, 2923.
18. Finar, I.L., Montgomery, A.J., J. Chem. Soc., 1961, 367.
19. Ogura, H., Kikuchi, K., Takayanagi, H., Furuhata, K., Iitaka, Y., Acheson, R.M., J.C.S. Perkin I, 1975, 2316.
20. Andreetti, G.D., Bocelli, G., Sgarabotto, P., Cryst. Struct. Commun., 3, 1974, 305.
21. Andreeti, G.D., Bocelli, G., Coghi, L., Sgarabotto, P., Cryst. Struct. Commun., 5, 1976, 315.
22. Pagani, G., Pagani, S.B., Tetrahedron Lett., 1968, 1041.
23. Davidson, R.M., Ph. D. Thesis, University of Kent (1981).
24. Budzikiewicz, H., Lenz, U., Org. Mass Spectrom., 10, 1975, 992.
25. Ciminale, F., Liso, G., Trapani, G., Tetrahedron Lett., 22, 1981, 1455.
26. Chiu, M.F., Gilbert, B.C., Hanson, P., J. Chem. Soc. B, 1970, 1700.
27. Tsujino, Y., Tetrahedron Lett., 1968, 411.
28. Jackson, C., Patel, N.K.D., Tetrahedron Lett., 1967, 2255.
29. Gorelik, M.V., Levandovskaya, T.V., Korolev, B.A., Terekhova, M.I., Petrov, E.S., Shatenshtein, A.I., J. Org. Chem. USSR (Engl. Transl.), 14, 1978, 2202.
30. [CA, 90, 1979, 10366.
31. Prota, G., Thomson, R.H., Endeavour, 35, 1976, 32.
32. Thomson, R.H., Angew. Chem., Int. Ed. Engl., 13, 1974, 305.
33. Prota, G., Riley, V., (eds.) “Pigmentation: Genesis and Biological Control”, 1972, Appleton, New York, 615.
34. Nicolaus, R.A., Prota, G., Santacroce, C., Scherillo, G., Sica, D., Gazz. Chim Ital., 99, 1969, 323.
35. Prota, G., Suarato, A., Nicolaus, R.A., Experientia, 27, 1971, 1381.
36. Agrup, G., Hansson, C., Rorsman, H., Rosengren, A-M., Rosengren, E., Acta Derm. Venereol., 58, 1978, 269.
37. [CA, 90, 1979, 36495.
38. Giordano, F., Mazzarella, L., Prota, G., Santacroce, C., Sica, D., J. Chem. Sec. C, 1971, 2610.
39. Kaul, B.L., Helv. Chim. Acta, 57, 1974, 2664.
40. Prota, G., Ponsiglione, E., Ruggiero, R., Tetrahedron, 30, 1974, 2781.
41. Chioccara, F., Novellino, E., Prota, G., Sodano, G., J.C.S. Chem. Commun., 1977, 50.
42. Prota, G., Scherillo, G., Petrillo, E., Nicolaus, R.A., Gazz. Chim. Ital., 99, 1969, 1193.
43. Sica, D., Santacroce, C., Prota, G., J. Heterocycl. Chem., 7, 1970, 1143.
44. Crescenzi, S., Misuraca, G., Novellino, E., Prota, G., Chim. Ind. (Milan), 57, 1975, 392.
45. Prota, G., Ponsiglione, E., Tetrahedron Lett., 1972, 1327.
46. Prota, G., Petrillo, O., Santacroce, C., Sica, D., J. Heterocycl. Chem., 7, 1970, 555.
47. Prota, G., Scherillo, G., Napolano, E., Nicolaus, R.A., Gazz. Chim. Ital., 97, 1967, 1451.
48. McCapra, F., Razavi, Z., J.C.S. Chem. Commun., 1976, 153.
49. Cricchio, R., Antonini, P., Lancini, G.C., Tamborini, G., White, R.J., Martinelli, E., Tetrahedron, 36, 1980, 1415.
50. Cricchio, R., Tetrahedron, 36, 1980, 2009.
51. Lednicer, D., Mitscher, L.A., “Organic Chemistry of Drug Synthesis,”, 1977, Wiley, New York, 372.
52. Bodea, C., Silberg, I., Adv. Heterocycl. Chem., 9, 1968, 321.
53. Fujii, K., Japanese Paent, 1958, 5241.
54. [CA, 53, 1959, 17156.
55. Lowrie, H.S., U.S. Patent 2,947,744 (1960).
56. [CA, 55, 1961, 583.
57. Winthrop, S.O. and Gaudry, R., U.S. Patent 2,989,528 (1961).
58. [CA, 56, 1962, 4777.
59. Krapcho, J., Turk, C.E., J. Med. Chem., 16, 1973, 776.
60. Millonig, R.C., Goldlust, M.B., Maguire, W.E., Rubin, B., Schulze, E., Wojnar, R.J., Turkheimer, A.R., Schreiber, W.F., Brittain, R.J., J. Med. Chem., 16, 1973, 780.
61. Lowrie, H.S., U.S. Patent 3,124,577 (1964).
62. [CA, 60, 1964, 14515.
63. Krapcho, J., U.S. Patent 3,143,545 (1964).
64. [CA, 61, 1964, 9507.
65. Krapcho, J., U.S. Patent 3,089,872 (1963).
66. [CA, 59, 1963, 11541.
67. Krapcho, J. and Yale, H.L., U.S. Patent 3,117,124 (1964).
68. [CA, 60, 1964, 8048.
69. Krapcho, J., Szabo, A., Williams, J., J. Med. Chem., 6, 1963, 214.
70. Krapcho, J., U.S. Patent 3,401,166 (1968).
71. [CA, 69, 1968, 106721.
72. Cavalla, J.F. and Michael, J., British Patent 1,244,481 (1971).
73. [CA, 75, 1971, 129824.
74. Mackie, A., Raeburn, J., J. Chem. Soc., 1952, 787.
75. Mackie, A., Stewart, G.M., Cutler, A.A., Misra, A.L., Br. J. Pharmacol. Chemother., 10, 1955, 7.
76. Mackie, A., Stewart, G.M., Arch. Int. Pharmacodyn. Ther., 102, 1955, 476.
77. Hoya, W.K., U.S. Patent 3,148,188 (1964).
78. [CA, 61, 1964, 13324.
79. Kano, H., Takahashi, S., Ogawa, Y., Yoshizaki, T., Kitakaze, T., Shionogi Kenkyusho Nempo, 11, 1961, 1.
80. [CA, 56, 1962, 4749.
81. Böshagen, H. and Plempel, M., U.S. Patent 3,911,126 (1975).
82. [CA, 84, 1976, 155700.
83. Prasad, R.N., J. Med. Chem., 12, 1969, 290.
84. Irmscher, K., Kraemer, J., Cimbollek, G., Orth, D., Novwack, H. and Freisberg, K.O., Ger. Offen. 1,809,454 (1970).
85. [CA, 73, 1970, 66594.
86. Lan, S.J., Chando, T.J., Cohen, A.I., Weliky, I., Schreiber, E.C., Drug Metab. Dispos., 1, 1973, 619.
87. Worley, J.W., U.S. Patent 3,923,709 (1975).
88. [CA, 84, 1976, 74279.
89. Yematsu, T., Hashimoto, S. and Oshio, H., British Patent 2,018,754 (1979).
90. [CA, 93, 1980, 46693.
91. Tanaka, R., Teramura, K. and Yokoyama, S., Japanese Patent 41/5833 (1966).
92. [CA, 65, 1966, 9062.
93. Dickey, J.B., Strain, W.H. and Corbitt, R.A., U.S. Patent 2,364,347 (1944).
94. [CA, 39, 1945, 4233.
95. Dickey, J.B. and McNally, J.G., U.S. Patent 2,374,181 (1945).
96. [CA, 40, 1946, 1180.
97. Convert, L. and Fabre, R., French Patent 1,344,437 (1963).
98. [CA, 61, 1964, 5885.
99. Rhone-Poulenc, S.A., French Patent 84,357 (1965).
100. [CA, 62, 1965, 14914.
101. I. Ya Postovskii, U.S.S.R. Patent 707,915 (1980).
102. [CA, 92, 1980, 148252.
103. Strain, W.H. and Dickey, J.B., U.S. Patent 2,381,935 (1945).
104. [CA, 40, 1964, 1889.
105. Mushkalo, L.K., Besemskaiya, V.A., Ukr. Khim. Zh., 18, 1952, 163.
106. [CA, 48, 1953, 13692.
107. Maki, Y., Suzuki, M., Chem. Pharm. Bull., 20, 1972, 832.
108. Kirchner, F.K., Alexander, E.J., J. Am. Chem. Soc., 81, 1959, 1721.
109. Mills, W.H., Whitworth, J.B., J. Chem. Soc., 1927, 2738.
110. Gobalenko, L.G., Mushkalo, L.K., Chiuguk, V.A., Ukr. Khim. Zh., 35, 1969, 1278.
111. [CA, 72, 1970, 78963.
112. Culvenor, C.C.J., Davies, W., Heath, N.S., J. Chem. Soc., 1949, 278.
113. Fusco, R., Palazzo, G., Gazz. Chim. Ital., 81, 1951, 735.
114. Kerwin, J.F., McCarty, J.E., VanderWerf, C.A., J. Org. Chem., 24, 1959, 1719.
115. Hromatka, O., Augl, J., Brazda, A., Grünsteidl, W., Monatsh. Chem., 90, 1959, 544.
116. Fujii, K., Yakugaku Zasshi, 77, 1957, 355.
117. [CA, 51, 1957, 12012.
118. Ishikawa, N., Sasaki, S., Bull. Chem. Soc. Jpn, 50, 1977, 2164.
119. Funke, A., Funke, G., Millet, B., Bull. Soc. Chim. Fr., 1961, 1524.
120. Duro, F., Condorelli, P., Scapini, G., Pappalardo, G., Ann. Chim. (Rome), 60, 1970, 383.
121. Duro, F., Condorelli, P., Ronsisvalle, G., Ann. Chim. (Rome), 63, 1973, 45.
122. Fujii, K., Yakugaku Zasshi, 77, 1957, 347.
123. [CA, 51, 1957, 12100.
124. Santacroce, C., Sica, D., Nicolaus, R.A., Gazz. Chim. Ital., 98, 1968, 85.
125. Curtze, J., Thomas, K., Liebigs Ann. Chem., 1974, 328.
126. Chioccara, F., Prota, G., Thomson, R.H., Tetrahedron Lett., 1975, 811.
127. Bottex, P., Sillion, B., de Gaudemaris, G., C. R. Hebd. Seances Acad. Sci., Ser. C, 267, 1968, 711.
128. Miyano, S., Abe, N., Sumoto, K., Teramato, K., J.C.S. Perkin I, 1976, 1146.
129. Kiprianov, A.I., Portnyagina, V.A., Zh. Obshch. Khim., 25, 1955, 2257.
130. [CA, 50, 1950, 9378.
131. Gupta, R.R., Ojha, K.G., Kalwania, G.S., Jumar, M., Heterocycles, 14, 1980, 1145.
132. Soni, R.P., Jain, M.L., Tetrahedron Lett., 21, 1980, 3795.
133. Langlet, N.A., Bi. Sven. Vetenskaps akad. Handl., 2211(No. 1), 1896, 8 [Beilstein 27, 34].
134. Hirano, H., Takamatsu, M., Sugiyama, K., Kurihara, T., Chem. Pharm. Bull., 27, 1979, 374.
135. Riolo, C.B., Ann. Chim. (Rome), 45, 1955, 1174.
136. Weidinger, H., Kranz, J., Chem. Ber., 97, 1964, 1599.
137. Elderfield, R.C., (eds.) “Heterocyclic Compounds,”, 5, 1957, Wiley, New York, 506.
138. Federsel, H.-J., Bergman, J., Tetrahedron Lett., 21, 1980, 2429.
139. Van Allen, J.A., Mee, J.D., Magguilli, C.A., Menion, R.S., J. Heterocycl. Chem., 12, 1975, 1005.
140. Chioccara, F., Nicolaus, R.A., Novellino, E., Prota, G., Chim. Ind. (Milan), 58, 1976, 546.
141. Chioccara, F., Prota, G., Nicolaus, R.A., Novellino, E., Synthesis, 1977, 876.
142. De Simone, F., Dini, A., Ramundo, E., La Bella, G., Rend. Accad. Sci. Fis. Mat., Naples, 44, 1977, 387.
143. [CA, 90, 1979, 54891.
144. De Simone, F., Dini, A., Nicolaus, R.A., Ramundo, E., Di Rosa, M., Persico, P., Farmaco, Ed. Sci., 35, 1980, 333.
145. [CA, 93, 1980, 132429.
146. Chioccara, F., Manciacapra, V., Novellino, E., Prota, G., J.C.S. Chem. Commun., 1977, 863.
147. Liso, G., Trapani, G., Latrofa, A., Marchini, P., J. Heterocycl. Chem., 18, 1981, 279.
148. Liso, G., Trapani, G., Reho, A., Latrofa, A., Tetrahedron Lett., 1981, 1641.
149. Hori, M., Kataoska, T., Shimizu, M., Imai, Y., Heterocycles, 9, 1978, 1413.
150. Chioccara, F., Oliva, L., Prota, G., Novellino, E., Synthesis, 1978, 744.
151. Hori, M., Kataoka, T., Shimizu, H., Imai, Y., Chem. Pharm. Bull., 27, 1979, 1982.
152. Hori, M., Kataoka, T., Shimizu, H., Imai, Y. and Ueda, N., Fukusokan Kagaku Toronkai Koen Yoshishu, 12th, 61 (1979) [CA93, 71673(1980)].
153. Hori, M., Kataoka, T., Shimizu, H., Ueda, N., Tetrahedron Lett., 22, 1981, 1701.
154. Sammes, P.G., Chem. Rev., 76, 1976, 113.
155. McKillop, A., Sayer, T.S.B., Bellinger, G.C.A., J. Org. Chem., 41, 1976, 1328.
156. Press, J.B., Eudy, N.H., Lovell, F.M., Perkinson, N.A., Tetrahedron Lett., 21, 1980, 1705.
157. Bouroais, J., C. R. Hebd. Seances Acad. Sci. Ser. C, 262, 1966, 1701.
158. Zienty, F.B., Vineyard, B.D., Schleppnik, A.A., J. Org. Chem., 27, 1962, 3140.
159. Friedlander, H., Chwala, C., Monatsh. Chem., 28, 1897, 271.
160. Claasz, M., Chem. Ber., 45, 1912, 2424.
161. Coutts, R.T., Peel, H.W., Smith, E.M., Can. J. Chem., 43, 1965, 3221.
162. Angelini, C., Grandolini, G., Ann. Chim. (Rome), 46, 1956, 235.
163. Honkanen, E., Virtanen, A., Acta Chem. Scand., 14, 1960, 1214.
164. Battistoni, P., Bruni, P., Fava, G., Synthesis, 1979, 220.
165. Battistoni, P., Bruni, P., Fava, G., Tetrahedron, 35, 1979, 1771.
166. Baldick, K.J., Lions, F., J. Proc. R. Soc. N.S.W., 71, 1938, 112.
167. [CA, 32, 1938, 34006.
168. Pagani, G., Maiorana, S., Chim. Ind. (Milan), 53, 1971, 468.
169. Zinke, T., Baeumer, J., Justus Liebigs Ann. Chem., 416, 1918, 86.
170. Coutts, R.T., Matthias, S.J., Peel, H.W., Can. J. Chem., 48, 1970, 2448.
171. Jackson, A.H., Johnston, D.N., Shannon, P.V.R., J.S.C. Chem. Commun., 1975, 911.
172. Shvedov, V.I., Altukhova, L.B., Lyubchanskaya, V.M., Grinev, A.N., Khim. Geterosikl. Soedin., 1972, 1509.
173. [CA, 78, 1973, 43395.
174. Carelli, V., Marchini, P., Micheletti-Moracci, F., Liso, G., Tetrahedron Lett., 1969, 3421.
175. Carelli, V., Marchini, P., Caroellini, M., Micheletti-Moracci, F., Liso, G., Lucarelli, M.G., Tetrahedron Lett., 1969, 4619.
176. Carelli, V., Micheletti-Moracci, F., Liberatore, F., Cardellini, M., Lucarelli, M.G., Marchini, P., Liso, G., Reho, A., Int. J. Sulf. Chem., 8, 1973, 267.
177. Marchini, P., Trapani, G., Liso, G., Berardi, V., Phosphorus and Sulphur, 3, 1977, 309.
178. Liso, G., Trapani, G., Bernardi, V., Marchini, P., J. Heterocycl. Chem., 17, 1980, 377.
179. Kuhn, R., Hammer, I., Chem. Ber., 84, 1951, 91.
180. Nabeta, K., Ichihara, A., Sakai, R., Sakumara, S., Agric. Biol. Chem., 36, 1972, 2261.
181. Holmes, T.J., Lawton, R.G., J. Am. Chem. Soc., 99, 1977, 1984.
182. Rai, M., Kumar, S., Krishan, K., Singh, A., Chem. Ind. (London), 1979, 26.
183. Di Bianca, F., Rivarola, E., Spek, A.L., Meinema, H.A., Noltes, J.G., J. Organomet. Chem., 63, 1973, 293.
184. Matsumara, Y., Shindo, M., Okawara, R., Inorg. Nucl. Chem. Lett., 3, 1967, 219.
185. Schmidbaur, H., Mitschke, K., Chem. Ber., 104, 1971, 1824.
186. Knyazev, V.N., Drozd, V.N., Minov, V.M., Tetrahedron Lett., 1976, 4825.
187. Prasad, R.N., Tietje, K., Can. J. Chem., 44, 1966, 1247.
188. Kiprianov, A.I., Pazenko, Z.N., Zh. Obshch. Khim., 21, 1951, 156.
189. [CA, 45, 1951, 7574.
190. Piechaczeck, J., Bojarska-Dahlig, H., Acta Pol. Pharm., 24, 1967, 244.
191. [CA, 69, 1968, 19098 (1968)].
192. Marchini, P., Liso, G., Reho, A., J. Org. Chem., 40, 1976, 3453.
193. Hirano, H., Sugiyama, K., Nagata, S., Kurihara, T., Chem. Pharm. Bull., 27, 1979, 2488.
194. Ciminale, F., DiNunno, L., Florio, S., Tetrahedron Lett., 1980, 3001.
195. Florida, S., Leng, J.L., Stirling, C.J.M., J. Heterocycl. Chem., 18, 1981, 857.
196. Worley, J.W., Ratts, K.W., Cammack, K.L., J. Org. Chem., 40, 1975, 1731.
197. Chandramohan, M.R., Sardessai, M.S., Shah, S.R., Seshadri, S., Indian J. Chem., 7, 1969, 1008.
198. Shah, S.R., Seshadri, S., Indian J. Chem., 10, 1972, 820.
199. Baliah, V., Rangarajan, T., J. Chem. Soc., 1960, 4703.
200. Kiprianov, A.I., Pazenko, Z.N., Zh. Obshch. Khim., 21, 1951, 170.
201. [CA, 45, 1951, 7576.
202. Shah, S.R., Seshadri, S., Indian J. Chem., 10, 1972, 977.
203. Coutts, R.T., Pound, N.J., Can. J. Chem., 48, 1970, 1859.
204. Coutts, R.T., Matthias, S.J., Mah, E., Pound, N.J., Can. J. Chem., 48, 1970, 3727.
205. Liso, G., Marchini, P., Reho, A., Micheletti-Moracci, F., Phosphorus and Sulphur, 2, 1976, 117.
206. Sica, D., Santacroce, C., Nicolaus, R.A., Gazz. Chim. Ital., 98, 1968, 488.
207. Coutts, R.T., Pound, N.J., J. Chem. Soc. C, 1971, 2696.
208. Maki, Y., Sako, M., Chem. Pharm. Bull., 24, 1976, 2250.
209. Boldt, P., Hermstedt, E., Z. Naturforsch. Anorg. Chem., Org. Chem., Biochem., Biophys., Biol., 22B, 1967, 718.