The document discusses the properties, synthesis, reactions, and medicinal uses of several aromatic heterocyclic compounds including pyrrole, furan, thiophene, pyrazole, imidazole, oxazole, thiazole, pyridine, azepines, quinoline, and isoquinoline. For each compound, key synthesis methods such as Paal-Knorr, Hantzsch, and Knorr reactions are described. Common reactions like electrophilic substitution and addition are also summarized. Medicinal applications are mentioned for several of the heterocycles.

2. CONTENT
Properties, synthesis, reactions & medicinal uses of…
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3. Properties
1. Aromaticity
PYRROLE
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4. Properties
1. Aromaticity
PYRROLE
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5. Properties
PYRROLE
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6. Synthesis
1. From Furans
PYRROLE
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7. Synthesis
2. Paal-Knorr synthesis
PYRROLE
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8. Synthesis
2. Paal-Knorr synthesis
PYRROLE
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9. Synthesis
3. Hantzsch Pyrrole synthesis
PYRROLE
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10. Synthesis
3. Hantzsch Pyrrole synthesis
PYRROLE
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11. Synthesis
4. Knorr synthesis
PYRROLE
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12. Synthesis
4. Knorr synthesis
Mechanism
PYRROLE
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13. Reactions
1. Electrophilic substitution
PYRROLE
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14. substitution reaction
Reactions
1. Electrophilic substitution
Pyrrole undergoes electrophilic
at 2nd position
PYRROLE
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15. Reactions
1. Electrophilic substitution
PYRROLE
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16. Reactions
2. Reduction
PYRROLE
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17. Reactions
3. Reimer Tiemann reaction
PYRROLE
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18. Reactions
PYRROLE
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19. Medicinal uses
PYRROLE
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20. Properties
1. Aromaticity
FURAN
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21. Properties
1. Aromaticity
FURAN
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22. Synthesis
1. Paal-Knorr synthesis of furan
FURAN
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23. Synthesis
1. Paal-Knorr synthesis of furan
FURAN
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24. Synthesis
2. Feist – Benary Synthesis
FURAN
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25. Synthesis
2. Feist – Benary Synthesis
Mechanism
FURAN
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26. Synthesis
3. From carbohydrate
FURAN
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27. Reactions
1. Electrophilic substitution
furan undergoes electrophilic substitution reaction at
2nd position
FURAN
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28. Reactions
1. Electrophilic substitution
FURAN
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29. Reactions
1. Electrophilic substitution
FURAN
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30. Reactions
2. Reduction
FURAN
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31. Reactions
3. Diels-Alder reaction
FURAN
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32. Reactions
3. Diels-Alder reaction
FURAN
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33. Reactions
4. Pyrrole synthesis
FURAN
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34. Medicinal uses
FURAN
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35. Properties
1. Aromaticity
THIOPHENE
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36. Properties
1. Aromaticity
THIOPHENE
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37. Properties
1. Aromaticity
THIOPHENE
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38. Synthesis
1. Paal-Knorr synthesis of thiophene
THIOPHENE
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39. Synthesis
1. Paal-Knorr synthesis of furan
Mechanism
THIOPHENE
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40. Synthesis
2. From sod. succinate
THIOPHENE
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41. Synthesis
3. Hinsberg Synthesis
THIOPHENE
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42. Reactions
1. Electrophilic substitution
thiophene undergoes electrophilic substitution reaction
at 2nd position
THIOPHENE
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43. Reactions
1. Electrophilic substitution
THIOPHENE
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44. Reactions
1. Electrophilic substitution
THIOPHENE
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45. Reactions
2. Reduction
THIOPHENE
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46. Reactions
3. reaction
THIOPHENE
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47. Medicinal uses
THIOPHENE
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48. Medicinal uses
THIOPHENE
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49. Properties
1. Aromaticity
PYRAZOLE
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50. Properties
1. Aromaticity
PYRAZOLE
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51. Properties
PYRAZOLE
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52. Synthesis
1. From pyrimidine
PYRAZOLE
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53. Synthesis
1. From pyrimidine
PYRAZOLE
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54. Synthesis
2. Knorr pyrazole synthesis
- .
PYRAZOLE
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55. Synthesis
2. Knorr pyrazole synthesis
mechanism
PYRAZOLE
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56. Synthesis
2. Knorr pyrazole synthesis
Examples
PYRAZOLE
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57. Synthesis
3. From Nitrile Imines
PYRAZOLE
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58. Synthesis
PYRAZOLE
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59. Reactions
PYRAZOLE
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60. Reactions
PYRAZOLE
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61. Reactions
PYRAZOLE
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62. Reactions
PYRAZOLE
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63. Reactions
PYRAZOLE
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64. Reactions
PYRAZOLE
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65. Reactions
PYRAZOLE
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66. Reactions
PYRAZOLE
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67. Medicinal Use
PYRAZOLE
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68. Properties
1. Aromaticity
IMIDAZOLE
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69. IMIDAZOLE
Properties
1. Aromaticity
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70. IMIDAZOLE
Properties
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71. IMIDAZOLE
Synthesis
71
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72. IMIDAZOLE
Synthesis
2. From an α- Halo - Carbonyl Component
What is α- Halo - Carbonyl Compound ????
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73. IMIDAZOLE
Synthesis
3. From Dehydrogenation of Imidazoline
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74. Reactions
1. Electrophilic addition to N
IMIDAZOLE
???
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75. Reactions
1. Electrophilic addition to N
IMIDAZOLE
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76. Reactions
1. Electrophilic addition to N
IMIDAZOLE
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77. Reactions
2. Electrophilic substitution to C
IMIDAZOLE
??
?
???
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78. Reactions
2. Electrophilic substitution to C
IMIDAZOLE
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79. Reactions
3. Imidazole catalyzed ester HL
IMIDAZOLE
Slow reaction due to weak Nu: (H2O)
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80. Reactions
3. Imidazole catalyzed ester HL
IMIDAZOLE
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81. Medicinal uses
IMIDAZOLE
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82. Medicinal uses
IMIDAZOLE
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83. Properties
1. Aromaticity
OXAZOLE
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84. Properties
1. Aromaticity
OXAZOLE
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85. Synthesis
1. Robinson-Gabriel synthesis
OXAZOLE
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86. Synthesis
1. Robinson-Gabriel synthesis
Mechanism
OXAZOLE
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87. Synthesis
2. From an α- Hydroxy - Carbonyl Component
OXAZOLE
α- Hydroxy - Carbonyl Component ????
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88. Synthesis
2. From an α- Hydroxy - Carbonyl Component
E.g.
OXAZOLE
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89. Synthesis
3. From Isocyanides
E.g.
OXAZOLE
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90. OXAZOLE
Reactions
1. Electrophilic addition to N
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91. OXAZOLE
Reactions
2. Electrophilic substitution to C
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92. OXAZOLE
Reactions
3. Diels-Alder Reaction
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93. OXAZOLE
Reactions
3. Diels-Alder Reaction
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94. OXAZOLE
Reactions
3. Diels-Alder Reaction
(2) Kondrat'eva pyridine synthesis
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95. OXAZOLE
Reactions
3. Diels-Alder Reaction
(2) Kondrat'eva pyridine synthesis
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96. OXAZOLE
Medicinal uses
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97. Properties
1. Aromaticity
THIAZOLE
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98. Properties
1. Aromaticity
THIAZOLE
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99. Synthesis
1. Gabriel synthesis
THIAZOLE
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100. Synthesis
1. Gabriel synthesis
Mechanism
THIAZOLE
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101. Synthesis
2. From an α- Hydroxy - Carbonyl Component
( Hantzsch Thiazole Synthesis)
THIAZOLE
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102. Synthesis
2. From an α- Hydroxy - Carbonyl Component
( Hantzsch Thiazole Synthesis)
Mechanism
THIAZOLE
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103. Synthesis
3. From an thiocyanate salts
THIAZOLE
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104. THIAZOLE
Reactions
1. Electrophilic addition to N
a. Protonation (basic property)
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105. THIAZOLE
Reactions
2. Electrophilic substitution to C
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106. THIAZOLE
Reactions
2. Electrophilic substitution to C
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107. THIAZOLE
Reactions
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108. THIAZOLE
Medicinal uses
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109. THIAZOLE
Medicinal uses
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110. Properties
1. Aromaticity
P Y R I D I N E
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111. Properties
1. Aromaticity
P Y R I D I N E
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112. Properties
2. Basicity
P Y R I D I N E
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113. Properties
2. Basicity
Pyridine is more basic than pyrrole
P Y R I D I N E
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114. Properties
2. Basicity
P Y R I D I N E
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115. Properties
2. Basicity
P Y R I D I N E
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116. Properties
3. Tautomerism
P Y R I D I N E
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117. P Y R I D I N E
Synthesis
1. Hantzsch pyridine synthesis
117
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118. P Y R I D I N E
Synthesis
1. Hantzsch pyridine synthesis
118
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119. P Y R I D I N E
Synthesis
1. Hantzsch pyridine synthesis
119
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120. P Y R I D I N E
Synthesis
2. The Guareschi Synthesis
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121. P Y R I D I N E
Synthesis
3. From 1,5 - Dicarbonyl Compounds
121
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122. P Y R I D I N E
Synthesis
4. From Oxazoles Kondrat'eva pyridine synthesis
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123. Reactions
1. Electrophilic addition to N
P Y R I D I N E
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124. Reactions
P Y R I D I N E
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125. P Y R I D I N E
C2
C3
C4
Reactions
2. Electrophilic substitution to C
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126. P Y R I D I N E
Reactions
2. Electrophilic substitution to C
126
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127. P Y R I D I N E
Reactions
2. Electrophilic substitution to C
127
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128. P Y R I D I N E
nucleophilic substitution
Reactions
3. Nucleophilic substitution
Why pyridine undergoes
reaction at 2-position.
C3
C2
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129. P Y R I D I N E
Reactions
3. Nucleophilic substitution
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130. P Y R I D I N E
Reactions
4. Pyridine as Nucleophilic catalyst
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131. P Y R I D I N E
Reactions
5. Reduction
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132. P Y R I D I N E
Medicinal uses
132
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133. P Y R I D I N E
Medicinal uses
133
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134. P Y R I D I N E
Medicinal uses
134
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135. Properties
1. Aromaticity
A Z E P I N E S
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136. Properties
2. Tautomerism
A Z E P I N E S
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137. A Z E P I N E S
Synthesis
1. Valence-bond Isomerization
137
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138. A Z E P I N E S
Synthesis
2. From Phenylazide
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139. A Z E P I N E S
Synthesis
3. From Nitrobenzene
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140. A Z E P I N E S
Reactions
140
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141. A Z E P I N E S
Reactions
3. Diels-Alder reaction
- 6+2 π electron reaction
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142. A Z E P I N E S
Medicinal Uses
142
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143. Properties
1. Aromatic
Q U I N O L I N E
143
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144. Synthesis
1. Skraup Quinoline synthesis
Q U I N O L I N E
144
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145. Synthesis
1. Skraup Quinoline synthesis
Mechanism
Q U I N O L I N E
145
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146. Q U I N O L I N E
Synthesis
1. Skraup Quinoline synthesis
146
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147. Synthesis
2. Doebner-Miller Synthesis
Q U I N O L I N E
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148. Synthesis
3. Friedlander Synthesis
Q U I N O L I N E
148
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149. Reactions
1. Electrophilic addition to N
Q U I N O L I N E
149
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150. Q U I N O L I N E
Reactions
2. Electrophilic aromatic substitution
150
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151. Reactions
3. Reduction reactions
Q U I N O L I N E
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152. Reactions
4. Oxidation
Q U I N O L I N E
152
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153. Q U I N O L I N E
Reactions
5. Nucleophilic substitution
153
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154. Medicinal uses
Q U I N O L I N E
154
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155. Medicinal uses
Q U I N O L I N E
155
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156. Properties
1. Aromatic
I S O Q U I N O L I N E
156
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157. Synthesis
1. Bischler-Napieralski Isoquinoline synthesis
I S O Q U I N O L I N E
157
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158. Synthesis
2. The Pictet – Gams synthesis
I S O Q U I N O L I N E
158
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159. Synthesis
3. Pomeranz–Fritsch synthesis
I S O Q U I N O L I N E
159
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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
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162. I S O Q U I N O L I N E
Reactions
3. Reduction reactions
162
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163. I S O Q U I N O L I N E
Reactions
4. Oxidation
163
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164. I S O Q U I N O L I N E
Reactions
5. Nucleophilic substitution
164
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165. I S O Q U I N O L I N E
Medicinal uses
165
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166. I S O Q U I N O L I N E
Medicinal uses
166
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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
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171. A C R I D I N E
Reactions
2. Electrophilic aromatic substitution
171
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172. A C R I D I N E
Reactions
3. Reduction reactions
172
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173. A C R I D I N E
Reactions
4. Oxidation
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174. A C R I D I N E
Reactions
5. Nucleophilic substitution
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175. A C R I D I N E
Medicinal uses
175
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176. Properties
1. Aromatic
I N D O L E
176
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177. I N D O L E
Synthesis
1. Fischer indole synthesis
177
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178. I N D O L E
Synthesis
1. Fischer indole synthesis
Mechanism
178
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179. I N D O L E
Synthesis
1. Fischer indole synthesis
Mechanism
179
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180. I N D O L E
Synthesis
1. Fischer indole synthesis
180
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181. I N D O L E
Synthesis
2. Bischler–Möhlau indole synthesis
181
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182. I N D O L E
Synthesis
3. Madelung synthesis
182
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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
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189. Reactions
2. Electrophilic aromatic substitution
I N D O L E
189
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190. Reactions
3. Reduction reactions
I N D O L E
190
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191. Reactions
4. Nucleophilic substitution
I N D O L E
191
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192. Medicinal uses
(1) Indole alkaloids :
I N D O L E
192
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193. Medicinal uses
I N D O L E
193
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194. Medicinal uses
I N D O L E
194
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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
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198. Synthesis
2. From    - Unsaturated Ketones
P Y R I M I D I N E
198
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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
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203. Reactions
3. Nucleophilic substitution
P Y R I M I D I N E
203
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204. Medicinal uses
P Y R I M I D I N E
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205. Medicinal uses
P Y R I M I D I N E
205
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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
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208. Properties
3. Tautomerism
P U R I N E
208
2018

209. Synthesis
1. Traube Synthesis
P U R I N E
209
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210. Synthesis
1. Traube Synthesis
P U R I N E
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211. Synthesis
2. From formamide
P U R I N E
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212. Synthesis
3. From substituted imidazole
P U R I N E
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213. Reactions
1. Electrophilic addition to N
P U R I N E
213
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214. P U R I N E
Reactions
2. Electrophilic aromatic substitution
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215. P U R I N E
Reactions
3. Nucleophilic substitution
215
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216. P U R I N E
Medicinal uses
216
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217. P U R I N E
Medicinal uses
217
2018