Literature DB >> 17685576

Selective amidation of 2,6-dihalogenopurines: application to the synthesis of new 2,6,9-trisubstituted purines.

Sandrine Piguel1, Michel Legraverend.   

Abstract

We report herein the palladium(0)/Xantphos-catalyzed cross-coupling of various amides with 2,6-dihalogenopurines, with substituent-dependent regioselectivity. Furthermore, subjecting the same 2,6-dihalogenopurines to SNAr conditions with amide/NaH in DMF leads to inverted regioselectivity albeit in lower yield. These methodologies allow the two-step synthesis of new 2,6,9-trisubstituted purines from readily available 2,6-dihalogenopurines.

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Year:  2007        PMID： 17685576     DOI： 10.1021/jo071196p

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  2 in total

1.  Pd-catalyzed N-arylation of secondary acyclic amides: catalyst development, scope, and computational study.

Authors:  Jacqueline D Hicks; Alan M Hyde; Alberto Martinez Cuezva; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

2.  Palladium-catalyzed C-N and C-O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols.

Authors:  Rajendra Surasani; Dipak Kalita; A V Dhanunjaya Rao; K B Chandrasekhar
Journal:  Beilstein J Org Chem       Date:  2012-11-19       Impact factor: 2.883
  2 in total

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