relation: http://d-scholarship-dev.library.pitt.edu/20407/
title: Microwave-assisted "libraries from libraries" approach toward the synthesis of allyl- and c-cyclopropylalkylamides
creator: Wipf, P
creator: Coleman, CM
creator: Janjic, JM
creator: Iyer, PS
creator: Fodor, MD
creator: Shafer, YA
creator: Stephenson, CRJ
creator: Kendall, C
creator: Day, BW
description: Cascade reactions of internal and terminal alkynes, zirconocene hydrochloride, dimethylzinc, and phosphinoyl imines (prepared in one step from aldehydes and diphenylphosphinoyl amide) lead to allylic phosphinoyl amides after aqueous workup. Microwave acceleration allows the completion of this one-pot reaction sequence in 10 min. These allylic amides can be converted into a variety of derivatives, including carbamates and sulfonamides, or reacted prior to workup with diiodomethane to give novel C-cyclopropylalkylamides. A solution-phase "libraries from libraries" approach was used to generate an intermediate 20-member library which was subsequently expanded to a 100-member library by a series of N-functionalizations. The biological activity was evaluated in an assay for competitive binding to the estrogen receptor (ERa), revealing three potent lead compounds of a new structural type. © 2005 American Chemical Society.
date: 2005-03-01
type: Article
type: PeerReviewed
format: text/plain
language: en
rights: attached
identifier: http://d-scholarship-dev.library.pitt.edu/20407/1/licence.txt
identifier:   Wipf, P and Coleman, CM and Janjic, JM and Iyer, PS and Fodor, MD and Shafer, YA and Stephenson, CRJ and Kendall, C and Day, BW  (2005) Microwave-assisted "libraries from libraries" approach toward the synthesis of allyl- and c-cyclopropylalkylamides.  Journal of Combinatorial Chemistry, 7 (2).  322 - 330.  ISSN 1520-4766     
relation: 10.1021/cc049842a