Heterocyclic Chemistry at a Glance

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204 Index


Messenger RNA 163
Metathesis 157
Methotrexate (Trexall) 178
Methoxsalen 179
N-Methyl-N-methylenemethaniminium chloride, in Mannich
substitutions 100
1-Methylpyrrolidin-2-one, see N-Methylpyrrolidone
N-Methylpyrrolidone (NMP) 150
Metronidazole (Flagyl) 176
Mevalonic acid 175
Minipress 173
Minisci reaction 15
mechanism 14
on 4-methylquinoline 15
on 4-phenylpyrimidine 15
on benzothiazole 15
on pyridine 15
Minoxidil (Rogaine) 173
Mirapex 174
-Molecular orbitals 4
Molipaxin 174
Montelukast (Singulair) 168, 170
Morphine 165
Morpholine 3
basicity 153
Motor neurone disease 174
mRNA, see Messenger RNA
Münchnone
dipolar cyloaddition reaction 116
ring synthesis 116
Muscarine 171
Mycotoxins 192
Mydriacyl 171


NADP (NADPH), see Nicotinamide adenine dinucleotide
phosphate
Naphthalene, structure 4
1,6-Napthyridine, 8-iodo-7-n-hexyl-, ring synthesis 70
2,7-Napthyridine, 3-trimethylsilyl-, ring synthesis 70
Naringin 175
Natural products 165, 169
Negishi reaction, examples 25, 27, 32, 54, 91, 92
Nettle rash, see Urticaria
Neurotransmitters 122, 158, 169, 173
Nexium 167
NFSI, see N-Fluoro-N-(phenylsulfonyl)benzenesulfonamide
NHC see N-Heterocyclic carbene
N-Heterocyclic carbenes 114
Niacin, see Vitamin B 3
Nickel(0)-catalysed Kumada–Corriu reaction 25
Nicotiana sp. 165
Nicotinamide adenine dinucleotide phosphate 160
Nicotine 165, 171
as insecticide 182
Nicotinic acid 41
Nimodipine, ring synthesis 45
Nitration, electrophilic 13
Nitrile imines, in ring synthesis of pyrazoles 120
Nitrile oxides
cycloaddition to alkyne 20
intramolecular cycloaddition across indole C-2-C-3
bond 93


in ring synthesis of 4,5-dihydroisoxazoles 120
of isoxazoles 120
Nitro-halo-benzenes, nucleophilic substitution 14
ortho-Nitrotoluenes, in indole ring synthesis 95
NMP, see N-Methylpyrrolidone
Nomenclature, // use in 1
(Z,E)-Nona-2,4-dienal, from pyrylium 72
Non-steroidal anti-infl ammatory drugs 174
Noradrenaline 169, 173
Norbornadiene, synthetic equivalent of ethyne in Diels-Alder
reactions 141
Norvasc 173
NSAIDS, see Non-steroidal anti-infl ammatory drugs
NTO 185
Nucleic acids 48
Nucleophilic radicals 14
Nucleophilic substitution, mechanism 13, 14
Nucleosides 122
Nucleotides 122

Ochratoxin A 192, 193
Olanzapine (Zyprexa) 167, 174
OLEDs, see Organic light emitting diodes
Omeprazole, mechanism of action 170, 171
Ondansetron (Zofran) 172
Optical brighteners 181
Organic light emitting diodes 193
Organocatalyst in addition of indole to conjugated aldehyde 88
Organocopper intermediates in palladium(0)-catalysed
reactions 28
Organolithium reagents 15
formation using LDA 16, 17
usingn-BuLi 16
usingt-BuLi 16
Organometallics in cross-couplings, selectivity 31, 32
Oxadiazinones, Diels–Alder 139
Oxadiazoles, ring synthesis 138, 139
1,2,3-Oxadiazole 137
1,2,4-Oxadiazole 137
1,2,5-Oxadiazole 137
3,4-diamino- (DAF) 185
decomposition with base 138
3-phenyl-, ring synthesis 139
1,3,4-Oxadiazole 137
1,3,4-Oxadiazin-6-one, 2-methoxycarbonyl-5-phenyl-,
Diels–Alder reaction 141
Oxanosine 123
1,2,3,4-Oxatriazoles 138
Oxaziridine 152
5-Oxazolone, 2-phenyl-, reaction with ethanal 115
Oxazoles
a 2-amino-4-cyano-, ring synthesis 117
2-amino-4-methyl-, reaction with phenacyl bromide 148
basicity 10, 107
4,5-dimethyl-, Diels–Alder reaction 115
2,5-diphenyl-, ring synthesis 117
disconnections for ring synthesis 116
2-lithio-, from oxazole 112
ring opening 112
4-methyl-, Diels–Alder reaction 114
numbering 2
2-phenyl, palladation and cross-coupling at C-5 30
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