Indoles - download pdf or read online

By R.J. Sundberg (Auth.)

ISBN-10: 0126769451

ISBN-13: 9780126769456

Content material:
Foreword

, Page vii
Preface

, Page viii
1 - Introduction

, Pages 1-6
2 - type Ia Cyclizations

, Pages 7-26
3 - classification Ib Cyclizations

, Pages 27-33
4 - type Ic Cyclizations

, Pages 35-44
5 - classification Ii Cyclization—The Hemetsberger Synthesis

, Pages 45-47
6 - classification IIab Cyclizations

, Pages 49-51
7 - class IIac Cyclizations

, Pages 53-78
8 - Indoles by means of Annelation of Pyrroles

, Pages 79-87
9 - man made amendment of Indoles by means of Substitution at Nitrogen

, Pages 89-93
10 - creation of Substituents at C2

, Pages 95-103
11 - creation of Substituents at C3

, Pages 105-118
12 - amendment of 3-Alkyl Substituents through Nucleophilic Substitution

, Pages 119-124
13 - advent of the Tryptamine and Tryptophan Side-Chains

, Pages 125-134
14 - creation of Substituents at the Carbocyclic Ring

, Pages 135-144
15 - Selective relief and Oxidation Reactions

, Pages 145-158
16 - man made Elaboration of Indole Derivatives utilizing Cycloaddition Reactions

, Pages 159-169
Index of Compounds and Methods

, Pages 171-175

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Additional info for Indoles

Example text

Hemetsberger, D. Knittel and H. Weidmann, Monatsh. Chem. 100, 1599 (1969); H. Hemetsberger, D. Knittel and H. Weidmann, Monatsh. Chem. 101, 161 (1970); H. Hemetsberger, D. Knittel and H. Weidmann, Monatsh. Chem. 103, 194 (1972). 2. C. J. Moody, J. Chem. , 1, 1333 (1984). 3. D. Knittel, Synthesis 186 (1985). 4. G. W. Hardy, D. Bull, H. T. Jones, G. Mills and G. Allan, Tetrahedron Lett. 9, 799 (1988). 5. D. M. B. Hickey, A. R. MacKenzie, C. J. Moody and C. W. Rees, J. Chem. , Perkin Trans. 1, 921 (1987).

The precipitate which resulted was collected by filtration, washed with water and dried over CaC12 in a vacuum desiccator. The dried precipitate was dissolved in EtOAc (600ml) and dried over Na2SO 4. _I r--~ r-I ~ ~ o~,~s OXOX i . ~ L . ~ 0 ~ n~ o~ ? 6 g) in 74% yield. 2 g, 79 mmol) was added as a solid slowly to refluxing xylene (500 ml) over a period of 3 h at a rate that prevented accumulation of unreacted azidocinnamate in the solution (monitored by gas evolution through a gas bubbler). The solution was refluxed for an additional 2 h after gas evolution ceased.

Chem. 41, 3775 (1976); G. Kollenz, Monatsh. Chem. 109, 249 (1978); G. P. Tokmakov, T. G. Zemlyanova and I. I. Grandberg, Chem. Heterocycl. , Engl. Transl. 22, 1345 (1986). 6. P. Schiess and A. Grieder, Tetrahedron Lett. 2097 (1969); P. Schiess and A. Grieder, Heir. Chim. Acta 57, 2643 (1974); P. Schiess and E. Seni, Helv. Chim. Acta 61, 1364 (1978). 7. Y. B. Vystoskii, N. M. Prsheval'skii, B. P. Zemskii, I. I. Grandberg and L. Y. Kostromina, Chem. Heterocycl. , Engl. Transl. 22, 713 (1986). 8. L.

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Indoles by R.J. Sundberg (Auth.)


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