Synthesis of Diversely Functionalized Hexahydropyrrolo[2,3-b]indoles Using Domino Reactions, Olefination, Isomerization and Claisen Rearrangement Followed by Reductive Cyclization

Hexahydropyrrolo[2,3-b]indoles 6 were synthesized in five steps from indolin-3-one 8 by a general and efficient method, in which elements of molecular diversity were readily added onto the 3a-position of the pyrrolo[2,3-b]indole ring system. Horner−Wadsworth−Emmons reaction of 2-allyloxyindolin-3-on...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-04, Vol.70 (8), p.2957-2966
Main Authors: Kawasaki, Tomomi, Ogawa, Atsuyo, Terashima, Romi, Saheki, Toshiko, Ban, Naoko, Sekiguchi, Hiroko, Sakaguchi, Ken-ei, Sakamoto, Masanori
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Combinatorial Chemistry Techniques
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Indicators and Reagents
Indole Alkaloids - chemistry
Indoles - chemical synthesis
Molecular Structure
Organic chemistry
Preparations and properties
Pyrroles - chemical synthesis
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Summary:Hexahydropyrrolo[2,3-b]indoles 6 were synthesized in five steps from indolin-3-one 8 by a general and efficient method, in which elements of molecular diversity were readily added onto the 3a-position of the pyrrolo[2,3-b]indole ring system. Horner−Wadsworth−Emmons reaction of 2-allyloxyindolin-3-ones 7, derived from indolin-3-one 8 and a variety of allylic alcohols, smoothly proceeded with successive Claisen rearrangement to give the corresponding 3-allyl-3-cyanomethylindolin-2-ones 15. Indolin-2-ones 15 were converted into pyrrolo[2,3-b]indoles 6 using partial hydrolysis followed by reductive cyclization with LiAlH4. Synthesis of N-methylated pyrrolo[2,3-b]indole derivatives 23 and 26 is also described.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo040289t