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Amit Z Chaudhari
CONTENT
2018 2
Properties, synthesis, reactions & medicinal uses of…
Properties
1. Aromaticity
PYRROLE
2018 3
Properties
1. Aromaticity
2018 4
PYRROLE
Properties
2018 5
PYRROLE
Synthesis
1. From Furans
2018 6
PYRROLE
Synthesis
2. Paal-Knorr synthesis
2018 7
PYRROLE
Synthesis
2. Paal-Knorr synthesis
2018 8
PYRROLE
Synthesis
3. Hantzsch Pyrrole synthesis
2018 9
PYRROLE
Synthesis
3. Hantzsch Pyrrole synthesis
2018 10
PYRROLE
Synthesis
4. Knorr synthesis
2018 11
PYRROLE
Synthesis
4. Knorr synthesis
Mechanism
2018 12
PYRROLE
Reactions
1. Electrophilic substitution
2018 13
PYRROLE
Reactions
1. Electrophilic substitution
Pyrrole undergoes electrophilic substitution reaction
at 2nd position
2018 14
PYRROLE
Reactions
1. Electrophilic substitution
2018 15
PYRROLE
Reactions
2. Reduction
2018 16
PYRROLE
Reactions
3. Reimer Tiemann reaction
2018 17
PYRROLE
Reactions
2018 18
PYRROLE
2018
Medicinal uses
19
PYRROLE
Properties
1. Aromaticity
FURAN
2018 20
Properties
1. Aromaticity
2018 21
FURAN
Synthesis
1. Paal-Knorr synthesis of furan
2018 22
FURAN
Synthesis
1. Paal-Knorr synthesis of furan
2018 23
FURAN
Synthesis
2. Feist – Benary Synthesis
2018 24
FURAN
Synthesis
2. Feist – Benary Synthesis
Mechanism
2018 25
FURAN
Synthesis
3. From carbohydrate
2018 26
FURAN
Reactions
1. Electrophilic substitution
furan undergoes electrophilic substitution reaction at
2nd position
2018 27
FURAN
Reactions
1. Electrophilic substitution
2018 28
FURAN
Reactions
1. Electrophilic substitution
2018 29
FURAN
Reactions
2. Reduction
2018 30
FURAN
Reactions
3. Diels-Alder reaction
2018 31
FURAN
Reactions
3. Diels-Alder reaction
2018 32
FURAN
Reactions
4. Pyrrole synthesis
2018 33
FURAN
2018
Medicinal uses
34
FURAN
Properties
1. Aromaticity
THIOPHENE
2018 35
Properties
1. Aromaticity
2018 36
THIOPHENE
Properties
1. Aromaticity
2018 37
THIOPHENE
Synthesis
1. Paal-Knorr synthesis of thiophene
2018 38
THIOPHENE
Synthesis
1. Paal-Knorr synthesis of furan
Mechanism
2018 39
THIOPHENE
Synthesis
2. From sod. succinate
2018 40
THIOPHENE
Synthesis
3. Hinsberg Synthesis
2018 41
THIOPHENE
Reactions
1. Electrophilic substitution
thiophene undergoes electrophilic substitution reaction
at 2nd position
2018 42
THIOPHENE
Reactions
1. Electrophilic substitution
2018 43
THIOPHENE
Reactions
1. Electrophilic substitution
2018 44
THIOPHENE
Reactions
2. Reduction
2018 45
THIOPHENE
Reactions
3. reaction
2018 46
THIOPHENE
2018
Medicinal uses
47
THIOPHENE
2018
Medicinal uses
48
THIOPHENE
Properties
1. Aromaticity
PYRAZOLE
2018 49
Properties
1. Aromaticity
PYRAZOLE
2018 50
Properties
PYRAZOLE
2018 51
Synthesis
1. From pyrimidine
PYRAZOLE
2018 52
Synthesis
1. From pyrimidine
PYRAZOLE
2018 53
Synthesis
2. Knorr pyrazole synthesis
- .
PYRAZOLE
2018 54
Synthesis
2. Knorr pyrazole synthesis
mechanism
PYRAZOLE
2018 55
Synthesis
2. Knorr pyrazole synthesis
Examples
PYRAZOLE
2018 56
Synthesis
3. From Nitrile Imines
PYRAZOLE
2018 57
Synthesis
PYRAZOLE
2018 58
Reactions
PYRAZOLE
2018 59
Reactions
PYRAZOLE
2018 60
Reactions
PYRAZOLE
2018 61
Reactions
PYRAZOLE
2018 62
Reactions
PYRAZOLE
2018 63
Reactions
PYRAZOLE
2018 64
Reactions
PYRAZOLE
2018 65
Reactions
PYRAZOLE
2018 66
Medicinal Use
PYRAZOLE
2018 67
Properties
1. Aromaticity
IMIDAZOLE
2018 68
IMIDAZOLE
2018
Properties
1. Aromaticity
69
IMIDAZOLE
2018
Properties
70
IMIDAZOLE
2018
Synthesis
71
IMIDAZOLE
2018
Synthesis
2. From an α- Halo - Carbonyl Component
What is α- Halo - Carbonyl Compound ????
72
IMIDAZOLE
2018
Synthesis
3. From Dehydrogenation of Imidazoline
73
Reactions
1. Electrophilic addition to N
2018
IMIDAZOLE
???
74
Reactions
1. Electrophilic addition to N
2018
IMIDAZOLE
75
Reactions
1. Electrophilic addition to N
2018
IMIDAZOLE
76
Reactions
2. Electrophilic substitution to C
2018
IMIDAZOLE
??? ???
77
Reactions
2. Electrophilic substitution to C
2018
IMIDAZOLE
78
Reactions
3. Imidazole catalyzed ester HL
2018
IMIDAZOLE
Slow reaction due to weak Nu: (H2O)
79
Reactions
3. Imidazole catalyzed ester HL
2018
IMIDAZOLE
80
Medicinal uses
2018
IMIDAZOLE
81
Medicinal uses
2018
IMIDAZOLE
82
Properties
1. Aromaticity
OXAZOLE
2018 83
2018
Properties
1. Aromaticity
OXAZOLE
84
2018
Synthesis
1. Robinson-Gabriel synthesis
OXAZOLE
85
2018
Synthesis
1. Robinson-Gabriel synthesis
Mechanism
OXAZOLE
86
2018
Synthesis
2. From an α- Hydroxy - Carbonyl Component
OXAZOLE
α- Hydroxy - Carbonyl Component ????
87
2018
Synthesis
2. From an α- Hydroxy - Carbonyl Component
E.g.
OXAZOLE
88
2018
Synthesis
3. From Isocyanides
E.g.
OXAZOLE
89
2018
OXAZOLE
Reactions
1. Electrophilic addition to N
90
2018
OXAZOLE
Reactions
2. Electrophilic substitution to C
91
2018
OXAZOLE
Reactions
3. Diels-Alder Reaction
92
2018
OXAZOLE
Reactions
3. Diels-Alder Reaction
93
2018
OXAZOLE
Reactions
3. Diels-Alder Reaction
(2) Kondrat'eva pyridine synthesis
94
2018
OXAZOLE
Reactions
3. Diels-Alder Reaction
(2) Kondrat'eva pyridine synthesis
95
2018
OXAZOLE
Medicinal uses
96
Properties
1. Aromaticity
THIAZOLE
2018 97
Properties
1. Aromaticity
THIAZOLE
2018 98
2018
Synthesis
1. Gabriel synthesis
THIAZOLE
99
2018
Synthesis
1. Gabriel synthesis
Mechanism
THIAZOLE
100
2018
Synthesis
2. From an α- Hydroxy - Carbonyl Component
( Hantzsch Thiazole Synthesis)
THIAZOLE
101
2018
Synthesis
2. From an α- Hydroxy - Carbonyl Component
( Hantzsch Thiazole Synthesis)
Mechanism
THIAZOLE
102
2018
Synthesis
3. From an thiocyanate salts
THIAZOLE
103
2018
THIAZOLE
Reactions
1. Electrophilic addition to N
a. Protonation (basic property)
104
2018
THIAZOLE
Reactions
2. Electrophilic substitution to C
105
2018
THIAZOLE
Reactions
2. Electrophilic substitution to C
106
2018
THIAZOLE
Reactions
107
2018
THIAZOLE
Medicinal uses
108
2018
THIAZOLE
Medicinal uses
109
Properties
1. Aromaticity
P Y R I D I N E
2018 110
2018
Properties
1. Aromaticity
P Y R I D I N E
111
2018
Properties
2. Basicity
P Y R I D I N E
112
2018
Properties
2. Basicity
Pyridine is more basic than pyrrole
P Y R I D I N E
113
2018
Properties
2. Basicity
P Y R I D I N E
114
2018
Properties
2. Basicity
P Y R I D I N E
115
2018
Properties
3. Tautomerism
P Y R I D I N E
116
2018
P Y R I D I N E
Synthesis
1. Hantzsch pyridine synthesis
117
2018
P Y R I D I N E
Synthesis
1. Hantzsch pyridine synthesis
118
2018
P Y R I D I N E
Synthesis
1. Hantzsch pyridine synthesis
119
2018
P Y R I D I N E
Synthesis
2. The Guareschi Synthesis
120
2018
P Y R I D I N E
Synthesis
3. From 1,5 - Dicarbonyl Compounds
121
2018
P Y R I D I N E
Synthesis
4. From Oxazoles Kondrat'eva pyridine synthesis
122
2018
Reactions
1. Electrophilic addition to N
P Y R I D I N E
123
2018
Reactions
P Y R I D I N E
124
2018
P Y R I D I N E
C2
C3
C4
Reactions
2. Electrophilic substitution to C
125
2018
P Y R I D I N E
Reactions
2. Electrophilic substitution to C
126
2018
P Y R I D I N E
Reactions
2. Electrophilic substitution to C
127
2018
P Y R I D I N E
Reactions
3. Nucleophilic substitution
Why pyridine undergoes nucleophilic substitution
reaction at 2-position.
128
C3
C2
2018
P Y R I D I N E
Reactions
3. Nucleophilic substitution
129
2018
P Y R I D I N E
Reactions
4. Pyridine as Nucleophilic catalyst
130
2018
P Y R I D I N E
Reactions
5. Reduction
131
2018
P Y R I D I N E
Medicinal uses
132
2018
P Y R I D I N E
Medicinal uses
133
2018
P Y R I D I N E
Medicinal uses
134
Properties
1. Aromaticity
A Z E P I N E S
2018 135
Properties
2. Tautomerism
A Z E P I N E S
2018 136
A Z E P I N E S
2018
Synthesis
1. Valence-bond Isomerization
137
A Z E P I N E S
2018
Synthesis
2. From Phenylazide
138
A Z E P I N E S
2018
Synthesis
3. From Nitrobenzene
139
A Z E P I N E S
2018
Reactions
140
A Z E P I N E S
2018
Reactions
3. Diels-Alder reaction
- 6+2 π electron reaction
141
A Z E P I N E S
2018
Medicinal Uses
142
2018
Properties
1. Aromatic
Q U I N O L I N E
143
2018
Synthesis
1. Skraup Quinoline synthesis
Q U I N O L I N E
144
2018
Synthesis
1. Skraup Quinoline synthesis
Mechanism
Q U I N O L I N E
145
2018
Q U I N O L I N E
Synthesis
1. Skraup Quinoline synthesis
146
2018
Synthesis
2. Doebner-Miller Synthesis
Q U I N O L I N E
147
2018
Synthesis
3. Friedlander Synthesis
Q U I N O L I N E
148
2018
Reactions
1. Electrophilic addition to N
Q U I N O L I N E
149
2018
Q U I N O L I N E
Reactions
2. Electrophilic aromatic substitution
150
2018
Reactions
3. Reduction reactions
Q U I N O L I N E
151
2018
Reactions
4. Oxidation
Q U I N O L I N E
152
2018
Q U I N O L I N E
Reactions
5. Nucleophilic substitution
153
2018
Medicinal uses
Q U I N O L I N E
154
2018
Medicinal uses
Q U I N O L I N E
155
2018
Properties
1. Aromatic
I S O Q U I N O L I N E
156
2018
Synthesis
1. Bischler-Napieralski Isoquinoline synthesis
I S O Q U I N O L I N E
157
2018
Synthesis
2. The Pictet – Gams synthesis
I S O Q U I N O L I N E
158
2018
Synthesis
3. Pomeranz–Fritsch synthesis
I S O Q U I N O L I N E
159
2018
I S O Q U I N O L I N E
Reactions
1. Electrophilic addition to N
160
2018
I S O Q U I N O L I N E
Reactions
2. Electrophilic aromatic substitution
161
2018
I S O Q U I N O L I N E
Reactions
3. Reduction reactions
162
2018
I S O Q U I N O L I N E
Reactions
4. Oxidation
163
2018
I S O Q U I N O L I N E
Reactions
5. Nucleophilic substitution
164
2018
I S O Q U I N O L I N E
Medicinal uses
165
2018
I S O Q U I N O L I N E
Medicinal uses
166
2018
Properties
1. Aromatic
A C R I D I N E
167
2018
Synthesis
1. From diphenyl amine-2-carboxylic acid
A C R I D I N E
168
2018
Synthesis
2. Bernthsen acridine synthesis
A C R I D I N E
169
2018
Reactions
1. Electrophilic addition to N
A C R I D I N E
170
2018
A C R I D I N E
Reactions
2. Electrophilic aromatic substitution
171
2018
A C R I D I N E
Reactions
3. Reduction reactions
172
2018
A C R I D I N E
Reactions
4. Oxidation
173
2018
A C R I D I N E
Reactions
5. Nucleophilic substitution
174
2018
A C R I D I N E
Medicinal uses
175
2018
Properties
1. Aromatic
I N D O L E
176
2018
I N D O L E
Synthesis
1. Fischer indole synthesis
177
2018
I N D O L E
Synthesis
1. Fischer indole synthesis
Mechanism
178
2018
I N D O L E
Synthesis
1. Fischer indole synthesis
Mechanism
179
2018
I N D O L E
Synthesis
1. Fischer indole synthesis
180
2018
I N D O L E
Synthesis
2. Bischler–Möhlau indole synthesis
181
2018
I N D O L E
Synthesis
3. Madelung synthesis
182
2018
I N D O L E
Synthesis
3. Madelung synthesis
E.g.
183
2018
Reactions
1. Electrophilic addition to N
I N D O L E
184
2018
Reactions
2. Electrophilic aromatic substitution
I N D O L E
185
2018
Reactions
2. Electrophilic aromatic substitution
I N D O L E
186
2018
Reactions
2. Electrophilic aromatic substitution
I N D O L E
187
2018
Reactions
2. Electrophilic aromatic substitution
I N D O L E
188
2018
Reactions
2. Electrophilic aromatic substitution
I N D O L E
189
2018
Reactions
3. Reduction reactions
I N D O L E
190
2018
Reactions
4. Nucleophilic substitution
I N D O L E
191
2018
Medicinal uses
(1) Indole alkaloids :
I N D O L E
192
2018
Medicinal uses
I N D O L E
193
2018
Medicinal uses
I N D O L E
194
2018
Properties
1. Aromatic
P Y R I M I D I N E
195
2018
Synthesis
1. From 1,3 - Dicarbonyl Compound
P Y R I M I D I N E
196
2018
Synthesis
1. From 1,3 - Dicarbonyl Compound
P Y R I M I D I N E
197
2018
Synthesis
2. From a , b - Unsaturated Ketones
P Y R I M I D I N E
198
2018
Synthesis
P Y R I M I D I N E
199
2018
Reactions
1. Electrophilic addition to N
P Y R I M I D I N E
200
2018
Reactions
2. Electrophilic aromatic substitution
P Y R I M I D I N E
201
2018
Reactions
3. Nucleophilic substitution
P Y R I M I D I N E
202
2018
Reactions
3. Nucleophilic substitution
P Y R I M I D I N E
203
2018
Medicinal uses
P Y R I M I D I N E
204
2018
Medicinal uses
P Y R I M I D I N E
205
2018
Medicinal uses
P Y R I M I D I N E
206
2018
Properties
1. Aromatic
P U R I N E
207
2018
Properties
3. Tautomerism
P U R I N E
208
2018
Synthesis
1. Traube Synthesis
P U R I N E
209
2018
Synthesis
1. Traube Synthesis
P U R I N E
210
2018
Synthesis
2. From formamide
P U R I N E
211
2018
Synthesis
3. From substituted imidazole
P U R I N E
212
2018
Reactions
1. Electrophilic addition to N
P U R I N E
213
2018
P U R I N E
Reactions
2. Electrophilic aromatic substitution
214
2018
P U R I N E
Reactions
3. Nucleophilic substitution
215
2018
P U R I N E
Medicinal uses
216
2018
P U R I N E
Medicinal uses
217
Heterocyclic compounds _ Organic Chemistry _ B. Pharm.

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Heterocyclic compounds _ Organic Chemistry _ B. Pharm.

Notas do Editor

  1. In a heterocyclic ring, other things being equal, numbering preferably commences at a saturated rather than at an unsaturated hetero atom
  2. https://www.synarchive.com/named-reactions/hantzsch-thiazole-synthesis