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