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Sundberg R.J. — Indoles

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Название: Indoles

Автор: Sundberg R.J.

Аннотация:

This volume is a valuable addition to the Best synthetic methods series, and the author and publishers are to be congratulated on producing a book that all concerned with nitrogen heterocyclic chemistry will find of considerable value.
— CHEMISTRY AND INDUSTRY
In his preface, Professor Sundberg states that he attempted to illustrate the most widely used synthetic methods in indole chemistry on the basis of the retrosynthetic concept of identifying the bonds being formed. Not only has he succeeded, but he hasdone an outstanding job...the book is an absolute must for those interested in indole chemistry...(it) describes most major classical methods and emphasizes all the newer methods available. Professor Sundberg is to be congratulated.

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Рубрика: Химия/

Статус предметного указателя: Готов указатель с номерами страниц

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Год издания: 1996

Количество страниц: 175

Добавлена в каталог: 06.11.2005

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Предметный указатель

1,3-dimethyl-5-methoxyoxindole, procedure for      153
1-(benzyloxycarbonyl)indole, procedure for      93
1-(phenylsulfonyl)indole, procedure for      97
1-(tert-butoxycarbony1)-2-cyclohexyltryptophan methyl ester, procedure for      133—134
1-(tert-butoxycarbonyl)-6-methoxyindole, procedure for      51
1-(tert-butoxycarbonyl)2-(4-cyanophenyl)indole, procedure for      100
1-acetyl-2,3-dihydroindole-2-sulfonic acid, as intermediate      137
1-acetyl-2-butyl-5-chloroindole, procedure for      24
1-benzyl 3-methyl 6-methoxyindole-1,3-dicarboxylate, procedure for      71
1-hydroxyindoles, synthesis of      8
1-methyl-5-fluorooxindole, procedure for      43
2-(2-methylphenyl)-1-(2-trimethylsilylethoxymethyl)indole, procedure for      100
2-(3- $\alpha$ -acetoxyandrost-16-en-17-yl)indole, procedure for      24
2-(4-phenylbutyl)indole, procedure for      29—30
2-(5-vinyl-l-azabicyclo[2.2.2]octan-2-ylindole, procedure for      50 51
2-(tert-butyl)indotl, procedure for      29
2-butanoyl-1-methylcarbazole, procedure for      168—169
2-phenylindole, procedure for      26
3,3,7-trimethyloxindole, procedure for      69
3-(2-aminoethy])-6-benzyloxy-1-methylindole, procedure for      128
3-(2-ammobutyl)indole, procedure for      128 129
3-(2-dimethylaminoethyl)-5-nitroindole, procedure for      91
3-(2-methyl-2-nitropropyl)indole, procedure for      123
3-(2-nitroethyl)indole, procedure for      122
3-(2-propenyl)indole, procedure for      108
3-(4-bromopropyl)-2-cyano-1-methylindole, procedure for      40—41
3-(cyclopenlanecarbonyl)indole, procedure for      115
3-acetyl-1-(phenylsulfonyl)indole, procedure for      115
3-acetyl-4-cyano-5-(indol-3-yl)pentan-2-one, procedure for      123
3-butanoyl-1-methylcarbazole, procedure for      168—169
3-cyanoindole, procedure for      116
3-ethyl-5-hydroxy-3-methylindole, procedure for      151
3-phenyl-1-(phenylsulfonyl)indole, procedure for      112
4-benzyloxyindole, procedure for      10
4-bromo-3-(2-methoxycarbonylethenyl)-1-(4-methyiphenylsulfonyl)indole, procedure for      112
4-carboxy-7-chloro-2-(ethoxycarbonyl)indole-3-propanoic acid, procedure for      68
4-chloroindole, procedure for      18
4-cyclohexyl-1-(4-methylphenylsulfonyl)indole, procedure for      81
5,6-bis-benzyloxy-4,7-dimethylindole, procedure for      13
5-benzyloxytryptophan, procedure for      133
5-ethyl 1-isobutyl, 6-(trimethylsilyl)indole-1,5-dicarboxylate, procedure for      87
6,7-dibromo-4-methoxyindole, procedure for      76 77
6-(4-fluorophenyl)indole, procedure for      143
6-benzoyloxindole, procedure for      19
6-bromooxindole, procedure for      19
6-chloroacetyl-1-(2,2-dimethylpropanoyl)indole, procedure for      137—138
6-methoxyindole-3-carboxaldehyde, procedure for      115 116
7-benzoyl-3-methyloxindole, procedure for      73—75
7-benzoylindole, procedure for      138
7-benzoyloxindole, procedure for      153
7-benzyloxy-3-methyl-5-nitroindole, procedure for      38
7-methoxyindole, procedure for      8
Acetanilides $\alpha$ -sulfinyl, oxindoles from      43
Acetanilides o-alkynyl, indoles from      21—24
Aldehydes $\alpha$ -alkylthio, indoles from      71—72
Aldehydes $\alpha$ -anilino, indoles from      41—44
Aldehydes o-aminobenzyl, indoles from      13—20
Aldehydes o-nitrobenzyl, indoles from      14—17
Anilides, o-acyl, indoles from anilides      32—33
Anilides, o-alkyl, indoles from anilides      27—30
Anilines, and $\gamma$ -baloacetoacetates, indoles from anilines      41
Anilines, indoles from by Gassman method      71—75
Anilines, N-allyl, indoles from anilines      35 38
Anilines, N-diethoxyethyl, indoles from anilines      41—42
Anilines, N-phenacyl, indoles from anilines      42—43 77
Anilines, N-propargyl, indoles from anilines      36—37
Anilines, N-vinyl, indoles from anilines      39—41
Anilines, o,N-diacyl, indoles from anilines      32—33
Anilines, o-acyl, indoles from anilines      30 32
Anilines, o-alkyl, indoles from anilines      27—30 45—46 49—50
Anilines, o-alkynyl, indoles from anilines      20 24
Anilines, o-chloroacetyl, indoles from anilines      75—77
Anilines, o-halo-N-vinyl, indoles from anilines      38—39
Anilines, oxindoles from anilines      73 75
Anilinosulfonium salts, in Gassman synthesis      71—75
aromaticity, of indole      2
Aziridines, reactions with indoles      106—107
Benzaldehydes, condensation with $\alpha$ -azidoacetate enolates      45
Benzanilides, indoles from      27—28
benzyl 2,3-dihydro-1-benzoyl-5-methoxyindole-3-propenoate, procedure for      146—147
Biscbler synthesis      77—78
Brunner reaction      69
Carbazole derivatives, 1-oxo-1,2,3,4,4a,9a-hexahydro      40
Carbazole derivatives, 4-oxo-1,2,3,4,4a,9a-hexahydro      40
Carbazole derivatives, synthesis from indoles      159—169
Chlorosulfonyl isocyanate, reaction with indole      113
Cinnamate esters, $\alpha$ -azido, indoles from      45 47
Cinnamate esters, o-nitro, indoles from      24—26
Cycloalka[b]indoles,oxidation of      155 157
Desulfurization, of 3-(alkylthio)indoles      71—72
Diels-Alder reaction of indole-2,3-quinodimethanes      164—169
Diels-Alder reaction of pyrrole-2,3-quinodimethanes      85—87
Diels-Alder reaction of vinylindoles      159—164
Diels-Alder reaction of vinylpyrroles      79 84—85
Dimethyl 2-acetamido-2-(7-chloroindol-3-yl)propanedicarboxylate, procedure for      62—63
Dimethyl acetylenedicarboxylate as catalyst for gramine alkylation      121
Dimethyl acetylenedicarboxylate reaction with vinylindoles      159
Dimethyl acetylenedicarboxylate reaction with vinylpyrroles      84
Enolates, indol-3-ylmethylation of      121—122
Epoxides, reactions with indoles      106—107
Ethyl 2,3-dihydroindole-2-carboxylate, procedure for      145—146
Ethyl 2-(ethoxycarbonyl)-2-formamido-3-(indol-3-yl)propenoate, procedure for      122
Ethyl 3-acetyl-5-hydroxy-8-methyl-6-(phenylsulfonyl)-1,2,3,6-tetrahydrohenzo[1,2-b:4,3-b’]dipyrrole-1-carboxylate, procedure for      147
Ethyl 4-[1-(phenylsulfonyl)indol-3-yl]butanoate, procedure for      151—152
Fischer indole synthesis      1 54—69
Fischer indole synthesis, anomalous products from Fischer indole synthesis      64—65
Fischer indole synthesis, catalysts and conditions for Fischer indole synthesis      54—55 59—61
Fischer indole synthesis, mechanism of Fischer indole synthesis      54—55
Fischer indole synthesis, regioselectivity of Fischer indole synthesis      56—59
Fischer indole synthesis, thermal      55
Friedel Crafts reaction for acylation of indoles      113—115 136—138
Friedel Crafts reaction, intramolecular      42 79—81
Furo[3,4-b]indoles      167
Gassman synthesis of indoles      71—73
Gassman synthesis of oxindoles      73—75
Gramine derivatives indole-2,3-quinodimethanes from gramine derivatives      164
Gramine derivatives lithiation of gramine derivatives      139
Gramine derivatives, alkylation with gramine derivatives      119—124
Heck reaction      16 109—111 131—132 141—143
Hemetsberger synthesis      45—47
Imino ethers, indoles from imino ethers      29
Indol-1-ylmagnesium halides      105—106
Indol-2-yl carbinols      95—98 150
Indol-2-ylborates      95 96 101
Indol-2-ylcopper reagents      97
Indol-2-ylstannanes      99—100 102
Indol-2-ylzinc halides      100
Indol-3-yl carbinols      149—150
Indol-3-ylsilanes      117
Indol-3-ylstannanes      111—112
Indol-3-ylzinc halides      111
Indol-4-ylsilanes      136
Indole derivatives from indolines      148—149
Indole derivatives, 1-acylation      92—93
Indole derivatives, 1-alkylation      89—92
Indole derivatives, 1-ulfonylation of indole derivatives      92—93
Indole derivatives, 2-acylation      100—103 150
Indole derivatives, 2-alkylation      95—98

Indole derivatives, 2-arylation      98—100
Indole derivatives, 2-carboxylation      100—102
Indole derivatives, 2-halogenation      102—103
Indole derivatives, 2-hydroxyalkylation      95 98
Indole derivatives, 2-vinyl      98—100 159—163
Indole derivatives, 3-acylation      113—116
Indole derivatives, 3-alkylation      105—109 149—152
Indole derivatives, 3-alkynylalion      109—113 129—131
Indole derivatives, 3-arylation      109—113
Indole derivatives, 3-carboxylation      113—116
Indole derivatives, 3-halogenation      117 118
Indole derivatives, 3-ulfenylation of ndole derivatives      117
Indole derivatives, 3-vinyl      109—113 159—163
Indole derivatives, acidity of indole derivatives      3 89
Indole derivatives, alkaloids      2 163 168
Indole derivatives, aromaticity of indole derivatives      2
Indole derivatives, basicity of indole derivatives      3
Indole derivatives, biologically active      1
Indole derivatives, drugs derived from indole derivatives      1—2
Indole derivatives, industrial synthesis      1
Indole derivatives, lithiation      95—98 100 107 117 139
Indole derivatives, nitroethenylation      125
Indole derivatives, nitroethylation      125
Indole derivatives, oxidation of indole derivatives      3 148—149 152—157
Indole derivatives, protecting groups for indole derivatives      91—93 95 99—100 107 139
Indole derivatives, reactivity of indole derivatives      3
Indole derivatives, reduction of indole derivatives      145—147 149—152
Indole derivatives, silylation of indole derivatives      117
Indole derivatives, thallation of indole derivatives      139—141 143
Indole-2,3-quinodimethanes      164—169
Indole-2-carbonitriles      40
Indole-2-carboxylate esters from $\alpha$ -anilino- $\beta$ -ketoesters      40
Indole-2-carboxylate esters from $\alpha$ -azidocinnamate esters      45 47
Indole-2-carboxylate esters from $\beta$ -ketoesters      65—68
Indole-2-carboxylate esters from pyruvate esters by Reissert method      14
Indole-2-carboxylate esters from pyruvate hyrazones      59 64 65—66
Indole-2-carboxylate ethyl ester, procedure for      25—26
Indole-2-ulfonamides      102
Indole-3-acetonitrile, procedure for      123
Indole-3-acetonitriles, tryptamines from      126
Indole-3-carbonitriles      29 113 116
Indole-3-carboxaldehyde, procedure for      115
Indole-3-carboxaldehydes, reactions of      126—128 131
Indole-3-carboxamides      113
Indole-3-carboxylate esters from $\beta$ -dialkylamino-o-nitrostyrenes      15
Indole-3-carboxylate esters from N-aryl-O-hydroxylamines and methyl propynoate      70—71
Indole-3-carboxylate esters from o-bromoanilines and acrylate esters      39
Indole-3-carboxylate esters from o-methanesulfonamido-phenylacetylenes      23
Indole-3-glyoxamides      125—128
Indole-7-carboxaldehyde, procedure for      141
Indoleboronic acids      111 143
Indolines 7-acylation of      136—137
Indolines alkylidene derivatives      36
Indolines aromatization of indolines      136—138 148—149
Indolines from indoles      145 147
Indolines lithiation of indolines      139
Indolines substitution reactions of indolines      136—137
Indolines tliallation of indolines      139—141
Indometbacin      51
Indot-3-ylmethyl halides      121—122 132
Japp-Klingemann synthesis of arylhydrazones      65—69
Ketones, $\alpha$ -alkylthio, indoles from ketones      71—72
Ketones, $\alpha$ -anilino, indoles from etones      41—44 77—78
Ketones, o-aminobenzyl, indoles from ketones      13—20
Ketones, o-nitrobenzyl, indoles from ketones      14—17
Lactams, acylation of indoles by lactams      113
Lactones, alkylation of indoles by lactones      91
Leimgruber-Batcho synthesis      7—11
Madelung synthesis      27—30
Mannich alkylation      106 119
Methyl $\alpha$ -hydroxy- $\alpha$ -methyl-1-(phenylsulfonyl)indole-2-acetate, procedure for      97—98
Methyl 1-(4-methylphenylsulfonyl)indole-4-( $\alpha$ -acetamidopropenoate), procedure for      143
Methyl 3-(4-fluorophenyl)-5-methylindole-2-carboxylate, procedure for      68
Methyl 4,6,7-trimethoxyindole-2-carboxylate, procedure for      46—47
Methyl 4-oxo-1,2,3,4-tetrahydrocarbazole-2-acetate, procedure for      157
Methyl 4-[5-(benzyloxycarbonyl)indol-3-yl]methyl-3-methoxy-benzoate, procedure for      108
Methyl 5-metboxy- $\alpha$ -oxo-1-(phenylsulfonyl)indole-2-acetate, procedure for      101—102
N,N-dihexyl-2-phenylindole-3-acetamide, procedure for      62
N,N-dimethyl-2-[5-(cyanomethyl )indol-3-yl]ethylamine, procedure for      63
N-aryl-O-hydroxylamines, indoles from      70—71
N-arylhydrazones, indoles from      54—69
N.N-dimethylformamide acetals of, in indole synthesis      8
o-aminobenzyl anion, synthons for      49—50
o-aminophcnylcthanols, indoles from      15—16
o-aminophenylacetylenes, indoles from      20 24
o-nitrobenzaldehydes, indoles from      11
o-nitrobenzyl cyanides, indoles from      16—17
o-nitrobenzylphosphonium salts, indoles from      28
o-nitrophenylacetic acid, oxindoles from      17
o-nitrophenylacetylenes, indoles from      20—24
o-nitrophenyldiazoninm salts, indoles from      15
o-nitrophenylethanols, indoles from      15
o-nitrostyrenes $\beta$ -dialkylamino, indoles from      7—11 14—15
o-nitrostyrenes, $\beta$ -nitro, indoles from      11—13 16
o-nitrostyrenes, indoles from      24—26
o-nitrostyrenes, oxindoles from      17
o-nitrotoluenes, indoles from      7—11
Oxindoles from $\alpha$ -haloacetanilides      42—43
Oxindoles from $\alpha$ -nitrophenylpyruvic acids      17
Oxindoles from $\alpha$ -sulfinylacetanilides      43
Oxindoles from indoles      152—154
Oxindoles from N-acylphenylhydrazines      69—70
Oxindoles from N-alkenoyl-o-haloanilines      37 38
Oxindoles from o-nitrophenylacetic acids      17
Palladium as catalyst for 2-arylation and vinylation      98—100
Palladium as catalyst for 3-allylation of indoles      108
Palladium as catalyst for carbocyclic substitution      141—143
Palladium as catalyst for carbonylation of indol-2-ylborates      101
Palladium as catalyst for coupling with alkynes      112
Palladium as catalyst for cyclization of N-allylanilines      35—38
Palladium as catalyst for cyclization of o-aminophenylacetylenes      20 24
Palladium as catalyst for cyclization of o-halo-N-vinylanilines      38 39
Palladium as catalyst for Heck reactions      16 109—111 131—132 141—143
Palladium as catalyst for oxidation of o-nitrostyrenes      16
Phase transfer catalysis      89 92
Pyrano[3,4-b]indol-3-ones      167
Pyrrole-2,3-quinodimethane intermediates      85—87
Pyrroles, indoles from      79—83
Pyrroles, vinyl derivatives, indoles from      84—85
Reductive cyclization of $\beta$ -dialkylamino-o-nitrostyrenes      8
Reductive cyclization of o,N-diacylanilnes      32 33
Reductive cyclization of o- $\beta$ -dinitrostyrenes      11
Reductive cyclization of o-chloroacetylanilines      75—77
Reductive cyclization of o-nitrophenylacetic acids to oxindoles      17
Reductive cyclization of o-nitrostyrenes      24—26
S-3-phenyl-2-[N-(trifluoroacetyl)pyrrolidin-2-yl]indole, procedure for      32—33
Sugasawa indole synthesis      75—77
Suzuki coupling reaction      111 143
Toluidines, indoles from      49
Tri-n-butyl phosphine, as catalyst for gramine alkylation      119—121
Tryptamine derivatives from piperidone-3-carboxylate esters      67
Tryptamine derivatives, by Fischer indole synthesis      61—63
Tryptamine derivatives, from diethyl (3-chloropropyl)malonate      67
Tryptamine derivatives, Grandberg method for      62
Tryptamine derivatives, synthesis of      67 125—129
Tryptophan derivatives      1
Tryptophan derivatives, synthesis of      107 109—110 129—134
Vilsmeier-Haack reagents      113

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