Saturated heterocycles
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1 Saturated heterocycles
2 Reac0ons of saturated heterocycles Saturated nitrogen heterocycles: amines, but more nucleophilic
3 Reac0ons of saturated heterocycles Saturated nitrogen heterocycles: amines, but more nucleophilic
4 Reac0ons of saturated heterocycles Aziridine: ring strain promotes ring opening
5 Reac0ons of saturated heterocycles Oxygen heterocycles
6 Reac0ons of saturated heterocycles Sulfur heterocycles
7 Heteroatoms in rings have axial and equatorial lone pairs
8 Some subs0tuents of saturated heterocycles prefer to be axial: the anomeric effect
9 Making heterocycles: ring- closing reac0ons
10 Making heterocycles: ring- closing reac0ons
11 Making heterocycles: ring- closing reac0ons
12 Thermodynamic control over ring size
13 The Thorpe Ingold effect
14 Baldwin s rules
15 Aroma0c Heterocycles
16 Aroma0city survives when parts of benzene s ring are replaced by nitrogen atoms
17 Pyridine is a very unreac0ve aroma0c imine
18 Pyridine is bad at electrophilic aroma0c subs0tu0on
19 Nucleophilic subs0tu0on is easy with pyridines
20 Ac0vated pyridines will do electrophilic aroma0c subs0tu0on Pyridine N- oxides are reac0ve towards both electrophilic and nucleophilic subs0tu0on
21 Pyridine as a catalyst and reagent
22 Five- membered aroma0c heterocycles are good at electrophilic subs0tu0on
23 Five- membered aroma0c heterocycles are good at electrophilic subs0tu0on
24 Furan and thiophene are oxygen and sulfur analogues of pyrrole Electrophilic addi0on may be preferred to subs0tu0on with furan
25 Lithia0on of thiophenes and furans
26 More reac0ons of five- membered heterocycles Nucleophilic subs0tu0on requires an ac0va0ng group Five- membered heterocycles act as dienes in Diels Alder reac0ons
27 More reac0ons of five- membered heterocycles Nitrogen anions can be easily made from pyrrole
28 Five- membered rings with two or more nitrogen atoms
29 Five- membered rings with two or more nitrogen atoms
30 Five- membered rings with two or more nitrogen atoms
31 Five- membered rings with two or more nitrogen atoms
32 Benzo- fused heterocycles Indoles are benzo- fused pyrroles
33 Aroma0city survives when parts of benzene s ring are replaced by nitrogen atoms
34 HOBt is an important reagent in pep0de synthesis
35 PuRng more nitrogen atoms in a six- membered ring
36 Fusing rings to pyridines: quinolines and isoquinolines
37 A nitrogen atom can be at a ring junc0on Fused rings with more than one nitrogen
38 Aroma0c heterocycles can have many nitrogens but only one sulfur or oxygen in any ring There are thousands more heterocycles out there
39 First of all, those every chemist must know: Which heterocyclic structures should you learn?
40 Which heterocyclic structures should you learn?
41 Aroma0c Heterocycles Synthesis Making heterocycles is easy that s precisely why there are so many of them. Just refl ect... Making C O, C N, and C S bonds is easy. Intramolecular reachons are preferred to intermolecular reachons. Forming fi ve- and six- membered rings is easy. We are talking about aromahc, that is, very stable molecules.
42 Thermodynamics is on our side Disconnect the carbon heteroatom bonds first
43 Disconnect the carbon heteroatom bonds first
44 Heterocycles with two nitrogen atoms come from the same strategy
45 Pyrroles, thiophenes, and furans from 1,4- dicarbonyl compounds
46 Pyrroles, thiophenes, and furans from 1,4- dicarbonyl compounds
47 How to make pyridines: the Hantzsch pyridine synthesis
48 How to make pyridines: the Hantzsch pyridine synthesis
49 Other syntheses of pyridines
50 Other syntheses of pyridines
51 Pyrazoles and pyridazines from hydrazine and dicarbonyl compounds
52 Chemistry hits the headlines Viagra
53 Chemistry hits the headlines Viagra
54 Pyrimidines can be made from 1,3- dicarbonyl compounds and amidines
55 Unsymmetrical nucleophiles lead to selec0vity ques0ons
56 Isoxazoles are made from hydroxylamine or by cycloaddi0on
57 Tetrazoles and triazoles are also made by cycloaddi0ons
58 The Fischer indole synthesis
59 The Fischer indole synthesis
60 The Fischer indole synthesis: sumatriptan
61 The Fischer indole synthesis: ondansetron
62 The Fischer indole synthesis: indomethacin
63 The Reissert indole synthesis
64 Quinolines and isoquinolines
65 Quinolines and isoquinolines
66 Quinolones also come from anilines by cycliza0on to an ortho posi0on
67 More heteroatoms in fused rings mean more choice in synthesis
68 Summary: the three major approaches to the synthesis of aroma0c heterocycles Ring construc0on by ionic cycliza0on
69 Summary: the three major approaches to the synthesis of aroma0c heterocycles Ring construc0on by ionic cycliza0on
70 Summary: the three major approaches to the synthesis of aroma0c heterocycles Ring construc0on by ionic cycliza0on
71 Summary: the three major approaches to the synthesis of aroma0c heterocycles Ring construc0on by cycloaddi0ons
72 Summary: the three major approaches to the synthesis of aroma0c heterocycles Ring modifica0on
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