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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