Journal
TETRAHEDRON
Volume 59, Issue 25, Pages 4615-4622Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(03)00627-6
Keywords
Diels-Alder; oxoindolinylidenes; spiroindolenines; phenanthridinone
Categories
Ask authors/readers for more resources
A new synthetic pathway to spiro[cyclohexane-1,3'-indoline]-2',4-diones was found starting from 3-chloromethylene-2-indolones 1 and Danishefsky's diene 2. Their synthesis consists of several steps involving the formation of the cycloadducts, the 6-chloro-4-trimethylsilyloxy-2-methoxyspiro[cyclohex-3-en-1,3'-indolin]-2'-one derivatives, transformed into spiro[cyclohexa-2,5-dienl,3'-indoline]-2',4-diones via 6-chloro-spiro[cyclohex-2-en-1,3'-indoline]-2',4-dione intermediates. The reduction of spiro[cyclohexa-2,5-dien-1,3'-indoline]-2',4-diones gave spiro[cyclohexane-1,3'-indoline]-2',4-diones 7. Using a 'one pot reaction', starting from 1 and 2, compounds 7 were obtained in satisfactory overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available