Heterocyclic Chemistry at a Glance

Index 213

Tosylmethyl isocyanide
in ring synthesis of pyrroles 84
of an imidazole 118
mechanism 118
of an oxazole 118
Transcription to mRNA 164
Transfer RNA 163
Transmetallation in palladium(0) catalysis 28–29
Traube synthesis of purines 130
Trazodone (Molipaxin) 174
Trexall 178
1,2,3-Triazines 139
ring synthesis from 1-aminopyrazole 142
stability 140
1,2,4-Triazines 139
6-chloro-3,5-bis(benzylamino)-, in Sonogashira
reaction 140
3-methylthio-, reaction with methoxide 140
3-methylthio-5,6-dimethyl-, ring synthesis 142
1,3,4-Triazine, Diels–Alder reaction 141
1,3,5-Triazines 139
2-amino-, from the heterocycle (Chichibabin) 140
bromination 140
2-bromo-, from the heterocycle 140
2,4-dibromo-, from 2-bromo-1,3,5-triazine 140
Diels–Alder reaction 141
reaction with 1,2-diaminobenzene 140
with ammonia 140
stability 140
Triazoles
N-alkylation 133
basicity 132
5-bromo-4-methoxycarbonyl-1-(4-nitrophenylmethyl)-,
ring synthesis 136
a 4,5-dihydro-, from azide cycloaddition 20
4,5-diphenyl-, reaction with CH 2 N 2 134
with MeI–AgNO 3 134
5-lithio-, 1-phenyl-, ring opening 135
1-(4-methoxyphenyl)-, ring synthesis 136
1-methyl-, bromination 133
5-methyl-1-phenyl-, from 5-lithio- 135
ring synthesis from azides 135, 136
tautomerism 132
1,2,3-Triazolo[1,5-a]pyridine 145
3-acetyl-, ring synthesis 147
nitration 146
ring opening and bromination 146
ring opening to diazo isomer 146
tautomerism 132
1,2,4-Triazoles
basicity 132
4-benzyl-, ring synthesis 136
chlorination 133
copper-catalysed N-1–arylation 30, 134
dibromination 133
3-fl uoro-1-methyl-5-methanesulfonyl-, reaction with
malonate anion 133
leaving group in purine chemistry 127
3-(pyridin-2-yl)-, ring synthesis 136
reaction with AcCl then MeI 134
with MeI–methoxide 134
tautomerism 132

1,2,4-Triazolo[1,5-a]pyridine 145

2-phenyl-, ring synthesis 147

1,2,4-Triazolo[4,3-a]pyridine 145

Tr i -t-butylphosphine 23

1,3,5-Tricarbonyl compounds, in ring synthesis

of 4-pyrones 75

Tricyclazole 184

1,3,3-Tri(ethoxy)prop-1-ene, synthetic equivalent

of malondialdehyde 46

Triethyl orthoformate, in ring synthesis of imidazoles

118, 119

Tr i fl ates as cross-coupling partners 27

Tr i fl uoroborates, in Suzuki–Miyaura reactions 24

Trimethoprim (Proloprim) 176

2,4,6-Trinitroresorcinol, lead salt 186

Triphenylphosphine 22

Tr i -o-tolylphosphine 23

Tris(dibenzylideneacetone)dipalladium(II)

(Pd 2 (dba) 3 ) 22

tRNA, see transfer RNA

Tropicamide (Mydriacyl) 171

Tryptamine 158

5-hydroxy-, see Serotonin

reaction with PhCH 2 CH=O 87

2-tri-n-butylstannyl-1-SEM-, in Stille reaction 91

Tryptophan 86, 158

synthesis using gramine 93

TTF, see Tetrathiafulvalene

TTF-TCNQ 193

Tubercidine 123

Tubocurarine 171

Tyrian purple 180

UTP, see Uridine triphosphate

UMP, see Uridine monophosphate

Uracil 48, 164, 165

N-arylation 56

5,6-diamino-, in ring synthesis of a pteridine 59

1,3-dimethyl-, reaction with guanidine 56

5-fl uoro-, bis-O-silylation 56

N-ribosylation 56

6-methyl-, reaction with formaldehyde 55

photodimerisation 55

ring synthesis 59

tautomerism 55

Uric acid 123, 124

from bio-oxidation of hypoxanthine 126

from bio-oxidation of xanthine 126

reaction with POCl 3 129

Uridine 48

a 5-bromo-, in Suzuki–Miyaura reaction 32

a 5-lithio 53

a 6-lithio- 53

Uridine monophosphate (UMP) 49

Uridine triphosphate (UTP) 49

Urticaria (nettle rash) 170

Valium 173

Valsartan (Diovan) 168

Van Leusen synthesis of pyrroles 84, 85

Variolin B 166

Vermox 176