Pharmaceutical organic chemistry

2. CONTENT
Properties, synthesis, reactions & medicinal uses of…
2
2018

3. Properties
1. Aromaticity
PYRROLE
3
2018

4. Properties
1. Aromaticity
PYRROLE
4
2018

5. Properties
PYRROLE
5
2018

6. Synthesis
1. From Furans
PYRROLE
6
2018

7. Synthesis
2. Paal-Knorr synthesis
PYRROLE
7
2018

8. Synthesis
2. Paal-Knorr synthesis
PYRROLE
8
2018

9. Synthesis
3. Hantzsch Pyrrole synthesis
PYRROLE
9
2018

10. Synthesis
3. Hantzsch Pyrrole synthesis
PYRROLE
10
2018

11. Synthesis
4. Knorr synthesis
PYRROLE
11
2018

12. Synthesis
4. Knorr synthesis
Mechanism
PYRROLE
12
2018

13. Reactions
1. Electrophilic substitution
PYRROLE
13
2018

14. substitution reaction
Reactions
1. Electrophilic substitution
Pyrrole undergoes electrophilic
at 2nd position
PYRROLE
14
2018

15. Reactions
1. Electrophilic substitution
PYRROLE
15
2018

16. Reactions
2. Reduction
PYRROLE
16
2018

17. Reactions
3. Reimer Tiemann reaction
PYRROLE
17
2018

18. Reactions
PYRROLE
18
2018

19. Medicinal uses
PYRROLE
19
2018

20. Properties
1. Aromaticity
FURAN
20
2018

21. Properties
1. Aromaticity
FURAN
21
2018

22. Synthesis
1. Paal-Knorr synthesis of furan
FURAN
22
2018

23. Synthesis
1. Paal-Knorr synthesis of furan
FURAN
23
2018

24. Synthesis
2. Feist – Benary Synthesis
FURAN
24
2018

25. Synthesis
2. Feist – Benary Synthesis
Mechanism
FURAN
25
2018

26. Synthesis
3. From carbohydrate
FURAN
26
2018

27. Reactions
1. Electrophilic substitution
furan undergoes electrophilic substitution reaction at
2nd position
FURAN
27
2018

28. Reactions
1. Electrophilic substitution
FURAN
28
2018

29. Reactions
1. Electrophilic substitution
FURAN
29
2018

30. Reactions
2. Reduction
FURAN
30
2018

31. Reactions
3. Diels-Alder reaction
FURAN
31
2018

32. Reactions
3. Diels-Alder reaction
FURAN
32
2018

33. Reactions
4. Pyrrole synthesis
FURAN
33
2018

34. Medicinal uses
FURAN
34
2018

35. Properties
1. Aromaticity
THIOPHENE
35
2018

36. Properties
1. Aromaticity
THIOPHENE
36
2018

37. Properties
1. Aromaticity
THIOPHENE
37
2018

38. Synthesis
1. Paal-Knorr synthesis of thiophene
THIOPHENE
38
2018

39. Synthesis
1. Paal-Knorr synthesis of furan
Mechanism
THIOPHENE
39
2018

40. Synthesis
2. From sod. succinate
THIOPHENE
40
2018

41. Synthesis
3. Hinsberg Synthesis
THIOPHENE
41
2018

42. Reactions
1. Electrophilic substitution
thiophene undergoes electrophilic substitution reaction
at 2nd position
THIOPHENE
42
2018

43. Reactions
1. Electrophilic substitution
THIOPHENE
43
2018

44. Reactions
1. Electrophilic substitution
THIOPHENE
44
2018

45. Reactions
2. Reduction
THIOPHENE
45
2018

46. Reactions
3. reaction
THIOPHENE
46
2018

47. Medicinal uses
THIOPHENE
47
2018

48. Medicinal uses
THIOPHENE
48
2018

49. Properties
1. Aromaticity
PYRAZOLE
49
2018

50. Properties
1. Aromaticity
PYRAZOLE
50
2018

51. Properties
PYRAZOLE
51
2018

52. Synthesis
1. From pyrimidine
PYRAZOLE
52
2018

53. Synthesis
1. From pyrimidine
PYRAZOLE
53
2018

54. Synthesis
2. Knorr pyrazole synthesis
- .
PYRAZOLE
54
2018

55. Synthesis
2. Knorr pyrazole synthesis
mechanism
PYRAZOLE
55
2018

56. Synthesis
2. Knorr pyrazole synthesis
Examples
PYRAZOLE
56
2018

57. Synthesis
3. From Nitrile Imines
PYRAZOLE
57
2018

58. Synthesis
PYRAZOLE
58
2018

59. Reactions
PYRAZOLE
59
2018

60. Reactions
PYRAZOLE
60
2018

61. Reactions
PYRAZOLE
61
2018

62. Reactions
PYRAZOLE
62
2018

63. Reactions
PYRAZOLE
63
2018

64. Reactions
PYRAZOLE
64
2018

65. Reactions
PYRAZOLE
65
2018

66. Reactions
PYRAZOLE
66
2018

67. Medicinal Use
PYRAZOLE
67
2018

68. Properties
1. Aromaticity
IMIDAZOLE
68
2018

69. IMIDAZOLE
Properties
1. Aromaticity
69
2018

70. IMIDAZOLE
Properties
70
2018

71. IMIDAZOLE
Synthesis
71
2018

72. IMIDAZOLE
Synthesis
2. From an α- Halo - Carbonyl Component
What is α- Halo - Carbonyl Compound ????
72
2018

73. IMIDAZOLE
Synthesis
3. From Dehydrogenation of Imidazoline
73
2018

74. Reactions
1. Electrophilic addition to N
IMIDAZOLE
???
74
2018

75. Reactions
1. Electrophilic addition to N
IMIDAZOLE
75
2018

76. Reactions
1. Electrophilic addition to N
IMIDAZOLE
76
2018

77. Reactions
2. Electrophilic substitution to C
IMIDAZOLE
??
?
???
77
2018

78. Reactions
2. Electrophilic substitution to C
IMIDAZOLE
78
2018

79. Reactions
3. Imidazole catalyzed ester HL
IMIDAZOLE
Slow reaction due to weak Nu: (H2O)
79
2018

80. Reactions
3. Imidazole catalyzed ester HL
IMIDAZOLE
80
2018

81. Medicinal uses
IMIDAZOLE
81
2018

82. Medicinal uses
IMIDAZOLE
82
2018

83. Properties
1. Aromaticity
OXAZOLE
83
2018

84. Properties
1. Aromaticity
OXAZOLE
84
2018

85. Synthesis
1. Robinson-Gabriel synthesis
OXAZOLE
85
2018

86. Synthesis
1. Robinson-Gabriel synthesis
Mechanism
OXAZOLE
86
2018

87. Synthesis
2. From an α- Hydroxy - Carbonyl Component
OXAZOLE
α- Hydroxy - Carbonyl Component ????
87
2018

88. Synthesis
2. From an α- Hydroxy - Carbonyl Component
E.g.
OXAZOLE
88
2018

89. Synthesis
3. From Isocyanides
E.g.
OXAZOLE
89
2018

90. OXAZOLE
Reactions
1. Electrophilic addition to N
90
2018

91. OXAZOLE
Reactions
2. Electrophilic substitution to C
91
2018

92. OXAZOLE
Reactions
3. Diels-Alder Reaction
92
2018

93. OXAZOLE
Reactions
3. Diels-Alder Reaction
93
2018

94. OXAZOLE
Reactions
3. Diels-Alder Reaction
(2) Kondrat'eva pyridine synthesis
94
2018

95. OXAZOLE
Reactions
3. Diels-Alder Reaction
(2) Kondrat'eva pyridine synthesis
95
2018

96. OXAZOLE
Medicinal uses
96
2018

97. Properties
1. Aromaticity
THIAZOLE
97
2018

98. Properties
1. Aromaticity
THIAZOLE
98
2018

99. Synthesis
1. Gabriel synthesis
THIAZOLE
99
2018

100. Synthesis
1. Gabriel synthesis
Mechanism
THIAZOLE
100
2018

101. Synthesis
2. From an α- Hydroxy - Carbonyl Component
( Hantzsch Thiazole Synthesis)
THIAZOLE
101
2018

102. Synthesis
2. From an α- Hydroxy - Carbonyl Component
( Hantzsch Thiazole Synthesis)
Mechanism
THIAZOLE
102
2018

103. Synthesis
3. From an thiocyanate salts
THIAZOLE
103
2018

104. THIAZOLE
Reactions
1. Electrophilic addition to N
a. Protonation (basic property)
104
2018

105. THIAZOLE
Reactions
2. Electrophilic substitution to C
105
2018

106. THIAZOLE
Reactions
2. Electrophilic substitution to C
106
2018

107. THIAZOLE
Reactions
107
2018

108. THIAZOLE
Medicinal uses
108
2018

109. THIAZOLE
Medicinal uses
109
2018

110. Properties
1. Aromaticity
P Y R I D I N E
110
2018

111. Properties
1. Aromaticity
P Y R I D I N E
111
2018

112. Properties
2. Basicity
P Y R I D I N E
112
2018

113. Properties
2. Basicity
Pyridine is more basic than pyrrole
P Y R I D I N E
113
2018

114. Properties
2. Basicity
P Y R I D I N E
114
2018

115. Properties
2. Basicity
P Y R I D I N E
115
2018

116. Properties
3. Tautomerism
P Y R I D I N E
116
2018

117. P Y R I D I N E
Synthesis
1. Hantzsch pyridine synthesis
117
2018

118. P Y R I D I N E
Synthesis
1. Hantzsch pyridine synthesis
118
2018

119. P Y R I D I N E
Synthesis
1. Hantzsch pyridine synthesis
119
2018

120. P Y R I D I N E
Synthesis
2. The Guareschi Synthesis
120
2018

121. P Y R I D I N E
Synthesis
3. From 1,5 - Dicarbonyl Compounds
121
2018

122. P Y R I D I N E
Synthesis
4. From Oxazoles Kondrat'eva pyridine synthesis
122
2018

123. Reactions
1. Electrophilic addition to N
P Y R I D I N E
123
2018

124. Reactions
P Y R I D I N E
124
2018

125. P Y R I D I N E
C2
C3
C4
Reactions
2. Electrophilic substitution to C
125
2018

126. P Y R I D I N E
Reactions
2. Electrophilic substitution to C
126
2018

127. P Y R I D I N E
Reactions
2. Electrophilic substitution to C
127
2018

128. P Y R I D I N E
nucleophilic substitution
Reactions
3. Nucleophilic substitution
Why pyridine undergoes
reaction at 2-position.
C3
C2
128
2018

129. P Y R I D I N E
Reactions
3. Nucleophilic substitution
129
2018

130. P Y R I D I N E
Reactions
4. Pyridine as Nucleophilic catalyst
130
2018

131. P Y R I D I N E
Reactions
5. Reduction
131
2018

132. P Y R I D I N E
Medicinal uses
132
2018

133. P Y R I D I N E
Medicinal uses
133
2018

134. P Y R I D I N E
Medicinal uses
134
2018

135. Properties
1. Aromaticity
A Z E P I N E S
135
2018

136. Properties
2. Tautomerism
A Z E P I N E S
136
2018

137. A Z E P I N E S
Synthesis
1. Valence-bond Isomerization
137
2018

138. A Z E P I N E S
Synthesis
2. From Phenylazide
138
2018

139. A Z E P I N E S
Synthesis
3. From Nitrobenzene
139
2018

140. A Z E P I N E S
Reactions
140
2018

141. A Z E P I N E S
Reactions
3. Diels-Alder reaction
- 6+2 π electron reaction
141
2018

142. A Z E P I N E S
Medicinal Uses
142
2018

143. Properties
1. Aromatic
Q U I N O L I N E
143
2018

144. Synthesis
1. Skraup Quinoline synthesis
Q U I N O L I N E
144
2018

145. Synthesis
1. Skraup Quinoline synthesis
Mechanism
Q U I N O L I N E
145
2018

146. Q U I N O L I N E
Synthesis
1. Skraup Quinoline synthesis
146
2018

147. Synthesis
2. Doebner-Miller Synthesis
Q U I N O L I N E
147
2018

148. Synthesis
3. Friedlander Synthesis
Q U I N O L I N E
148
2018

149. Reactions
1. Electrophilic addition to N
Q U I N O L I N E
149
2018

150. Q U I N O L I N E
Reactions
2. Electrophilic aromatic substitution
150
2018

151. Reactions
3. Reduction reactions
Q U I N O L I N E
151
2018

152. Reactions
4. Oxidation
Q U I N O L I N E
152
2018

153. Q U I N O L I N E
Reactions
5. Nucleophilic substitution
153
2018

154. Medicinal uses
Q U I N O L I N E
154
2018

155. Medicinal uses
Q U I N O L I N E
155
2018

156. Properties
1. Aromatic
I S O Q U I N O L I N E
156
2018

157. Synthesis
1. Bischler-Napieralski Isoquinoline synthesis
I S O Q U I N O L I N E
157
2018

158. Synthesis
2. The Pictet – Gams synthesis
I S O Q U I N O L I N E
158
2018

159. Synthesis
3. Pomeranz–Fritsch synthesis
I S O Q U I N O L I N E
159
2018

160. I S O Q U I N O L I N E
Reactions
1. Electrophilic addition to N
160
2018

161. I S O Q U I N O L I N E
Reactions
2. Electrophilic aromatic substitution
161
2018

162. I S O Q U I N O L I N E
Reactions
3. Reduction reactions
162
2018

163. I S O Q U I N O L I N E
Reactions
4. Oxidation
163
2018

164. I S O Q U I N O L I N E
Reactions
5. Nucleophilic substitution
164
2018

165. I S O Q U I N O L I N E
Medicinal uses
165
2018

166. I S O Q U I N O L I N E
Medicinal uses
166
2018

167. Properties
1. Aromatic
A C R I D I N E
167
2018

168. Synthesis
1. From diphenyl amine-2-carboxylic acid
A C R I D I N E
168
2018

169. Synthesis
2. Bernthsen acridine synthesis
A C R I D I N E
169
2018

170. Reactions
1. Electrophilic addition to N
A C R I D I N E
170
2018

171. A C R I D I N E
Reactions
2. Electrophilic aromatic substitution
171
2018

172. A C R I D I N E
Reactions
3. Reduction reactions
172
2018

173. A C R I D I N E
Reactions
4. Oxidation
173
2018

174. A C R I D I N E
Reactions
5. Nucleophilic substitution
174
2018

175. A C R I D I N E
Medicinal uses
175
2018

176. Properties
1. Aromatic
I N D O L E
176
2018

177. I N D O L E
Synthesis
1. Fischer indole synthesis
177
2018

178. I N D O L E
Synthesis
1. Fischer indole synthesis
Mechanism
178
2018

179. I N D O L E
Synthesis
1. Fischer indole synthesis
Mechanism
179
2018

180. I N D O L E
Synthesis
1. Fischer indole synthesis
180
2018

181. I N D O L E
Synthesis
2. Bischler–Möhlau indole synthesis
181
2018

182. I N D O L E
Synthesis
3. Madelung synthesis
182
2018

183. I N D O L E
Synthesis
3. Madelung synthesis
E.g.
183
2018

184. Reactions
1. Electrophilic addition to N
I N D O L E
184
2018

185. Reactions
2. Electrophilic aromatic substitution
I N D O L E
185
2018

186. Reactions
2. Electrophilic aromatic substitution
I N D O L E
186
2018

187. Reactions
2. Electrophilic aromatic substitution
I N D O L E
187
2018

188. Reactions
2. Electrophilic aromatic substitution
I N D O L E
188
2018

189. Reactions
2. Electrophilic aromatic substitution
I N D O L E
189
2018

190. Reactions
3. Reduction reactions
I N D O L E
190
2018

191. Reactions
4. Nucleophilic substitution
I N D O L E
191
2018

192. Medicinal uses
(1) Indole alkaloids :
I N D O L E
192
2018

193. Medicinal uses
I N D O L E
193
2018

194. Medicinal uses
I N D O L E
194
2018

195. Properties
1. Aromatic
P Y R I M I D I N E
195
2018

196. Synthesis
1. From 1,3 - Dicarbonyl Compound
P Y R I M I D I N E
196
2018

197. Synthesis
1. From 1,3 - Dicarbonyl Compound
P Y R I M I D I N E
197
2018

198. Synthesis
2. From    - Unsaturated Ketones
P Y R I M I D I N E
198
2018

199. Synthesis
P Y R I M I D I N E
199
2018

200. Reactions
1. Electrophilic addition to N
P Y R I M I D I N E
200
2018

201. Reactions
2. Electrophilic aromatic substitution
P Y R I M I D I N E
201
2018

202. Reactions
3. Nucleophilic substitution
P Y R I M I D I N E
202
2018

203. Reactions
3. Nucleophilic substitution
P Y R I M I D I N E
203
2018

204. Medicinal uses
P Y R I M I D I N E
204
2018

205. Medicinal uses
P Y R I M I D I N E
205
2018

206. Medicinal uses
P Y R I M I D I N E
206
2018

207. Properties
1. Aromatic
P U R I N E
207
2018

208. Properties
3. Tautomerism
P U R I N E
208
2018

209. Synthesis
1. Traube Synthesis
P U R I N E
209
2018

210. Synthesis
1. Traube Synthesis
P U R I N E
210
2018

211. Synthesis
2. From formamide
P U R I N E
211
2018

212. Synthesis
3. From substituted imidazole
P U R I N E
212
2018

213. Reactions
1. Electrophilic addition to N
P U R I N E
213
2018

214. P U R I N E
Reactions
2. Electrophilic aromatic substitution
214
2018

215. P U R I N E
Reactions
3. Nucleophilic substitution
215
2018

216. P U R I N E
Medicinal uses
216
2018

217. P U R I N E
Medicinal uses
217
2018