Chapter 21. Organic Chemistry 4 th Edition Paula Yurkanis Bruice. More About Amines. Heterocyclic Compounds
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1 Organic Chemistry 4 th Edition Paula Yurkanis Bruice Chapter 21 More About Amines. Heterocyclic Compounds Irene Lee Case Western Reserve University Cleveland, OH 2004, Prentice Hall
2 Amines An amine is a base as well as a nucleophile Some amines are heterocyclic compounds (or heterocycles) Most drugs, vitamins, and many other natural products are heterocycles A natural product is a compound synthesized by a plant or an animal
3 Alkaloids are natural products that contain one or more nitrogen heteroatoms
4 More About Nomenclature of Heterocycles Cyclic amines H N azacylclopropane aziridine NH azacyclobutane azetidine N H CH 3 3-methylazacyclopentane 3-methylpyrrolidine N H CH 3 N 2-methylazacyclohexane 2-methylpiperidine CH 2 CH 3 N-ethylazacyclopentane N-ethylpyrrolidine
5 Heterocycles with oxygen and sulfur heteroatoms O S O oxacyclopropane oxirane ethylene oxide thiacyclopropane thiirane oxacyclobutane oxetane O O oxacyclopentane tetrahydrofuran O tetrahydropyran O 1,4-dioxane
6 The lone-pair electrons on nitrogen allows an amine to turn inside out rapidly at room temperature
7 Amines are the most common organic bases Saturated heterocycles containing five or more atoms have physical and chemical properties typical of their acyclic analogs
8 Reactions of Amines nucleophilic substitution reactions CH 3 CH 2 Br + CH 3 NH 2 CH 3 CH 2 NH 2 CH 3 Br CH 3 CH 2 NHCH 3 + HBr nucleophilic acyl substitution reactions O O CH 3 CH 2 C Cl + 2 CH 3 NH 2 CH 3 CH 2 C NHCH 3 + CH 3 NH 3 Cl
9 nucleophilic addition elimination reactions O + HN N + H 2 O conjugate addition reactions CH 3 O CH 3 O CH 3 C CHCH + CH 3 NH CH 3 C CH 2 CH CH 3 NCH 3 CH 3
10 Relative Reactivity of Amine most reactive least reactive RCH 2 F > RCH 2 OH ~ RCH 2 OCH 3 > RCH 2 NH 2 HF H 2 O RCH 2 OH NH 3 pk a = 3.2 pk a = 15.7 pk a = 15.5 pk a = 36 The leaving group of a protonated amine cannot dissociate to form a carbocation or be replaced by a halide ion
11 Reactions of Quaternary Ammonium Hydroxides A Hofmann elimination is an E2 reaction The leaving group of a quaternary ammonium ion has about the same leaving tendency as a protonated amino group
12 The hydrogen is removed from the -carbon bonded to the most hydrogens A strong base such as hydroxide ion must be used in the elimination reaction
13
14 Quaternary ammonium salts are used as phase transfer catalysts in facilitating the reactions between certain ionic and organic reactants
15 Consider the reaction between sodium cyanide and an alkyl halide
16 Oxidation of Amines oxd oxd oxd R NH 2 R NH OH R N O R N+ a hydroxylamine a nitroso compound O- O R R R R NH + H 2 O 2 R N+ OH H + OH - R N OH + H 2 O R R R R N R + H 2 O 2 R N+ R + OH - R N R OH O_ + H 2 O
17 Amine Oxides Undergo a Cope Elimination Reaction
18 The Gabriel Synthesis of Primary Amines
19 Other Methods for Synthesizing Amines - 1. N 3 CH 3 CH 2 CH 2 CH 2 Br CH 3 CH 2 CH 2 CH 2 NH 2 2. H 2, Pd/C 1. NaCN, HCl 2. H 2, Pd/C CH 3 CH 2 CH 2 CH 2 CH 2 NH 2
20 O 1. LiALH 4 R NH 2 2. H 2 O RCH 2 NH 2 O 1. LiALH 4 R NHCH 3 2. H 2 O RCH 2 NHCH 3 O R NCH 3 CH 3 1. LiALH 4 2. H 2 O RCH 2 NCH 3 CH 3
21 Reduction of Nitro Compounds CH 3 CH 2 NO 2 + H 2 Pd/C CH 3 CH 2 NH 2 Pd/C NO 2 + H 2 NH 2
22 Reductive Amination econdary and tertiary amines can be prepared from mines and enamines by reducing the imines or enamines
23 Aromatic Five-Membered Heterocycles
24 Pyrrole is an extremely weak base
25 The dipole moment in pyrrolidine (left) is attributed to the electron-withdrawing property of the nitrogen atom
26
27 Pyrrole, furan, and thiophene undergo electrophilic substitution preferentially at C-2
28
29
30 The relative reactivities of the five-membered-ring heterocycles in Friedel Crafts reaction
31 The resonance hybrid of pyrrole indicates that there is a partial positive charge on the nitrogen Pyrrole is unstable in strongly acid solution because the protonated pyrrole polymerizes Pyrrole s acidity is increased due to its conjugated base being stabilized by resonance
32
33 indole N H O benzofuran S benzothiophene
34 Aromatic Six-Membered-Ring Heterocycles
35 The pyridinium ion is a stronger acid than a typical ammonium ion
36 Pyridine Is a Tertiary Amine
37 Pyridine undergoes electrophilic aromatic substitution at C-3
38 Pyridine undergoes nucleophilic aromatic substitution at C-2 and C-4
39 Bromination and Oxidation of Substituted Pyridine
40 Diazotization of Aminopyridine
41
42 The -hydrogens of alkyl substituents can be removed by base to generate nucleophiles
43 Quinoline and isoquinoline are known as benzopyridines
44 Some Biologically Important Heterocycles Imidazole
45
46
47 Porphyrin
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