Literature DB >> 18275209

Selective synthesis of spiro[4,5]trienyl acetates via an intramolecular electrophilic ipso-iodocyclization process.

Bo-Xiao Tang1, Dong-Jun Tang, Shi Tang, Quan-Fu Yu, Yue-Hua Zhang, Yun Liang, Ping Zhong, Jin-Heng Li.   

Abstract

A general and efficient intramolecular electrophilic ipso-iodocyclization of para-unactivated arylalkynes has been developed for the synthesis of spiro[4,5]trienyl acetates. In the presence of NIS (N-iodosuccimide) and HOAc, para-unactivated arylalkynes, including N-arylpropiolamides and phenyl 3-phenylpropiolate, underwent the intramolecular electrophilic ipso-iodocyclization smoothly in moderate to good yields.

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Year:  2008        PMID： 18275209     DOI： 10.1021/ol703050z

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu(4)NI-induced electrophilic cyclization.

Authors:  Yu Chen; Chul-Hee Cho; Feng Shi; Richard C Larock
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

Review 2.  Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.

Authors:  Imtiaz Khan; Aliya Ibrar; Sumera Zaib
Journal:  Top Curr Chem (Cham)       Date:  2021-01-05

3.  Iodine/palladium approaches to the synthesis of polyheterocyclic compounds.

Authors:  Saurabh Mehta; Richard C Larock
Journal:  J Org Chem       Date:  2010-03-05       Impact factor: 4.354

4.  Studies Towards the Leucetta-derived Alkaloids Spirocalcaridine A and B - Possible Biosynthetic Implications.

Authors:  Panduka B Koswatta; Jayanta Das; Muhammed Yousufuddin; Carl J Lovely
Journal:  European J Org Chem       Date:  2015-04

5.  Competition studies in alkyne electrophilic cyclization reactions.

Authors:  Saurabh Mehta; Jesse P Waldo; Richard C Larock
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

6.  A simple and mild synthesis of 1H-isochromenes and (Z)-1-alkylidene-1,3-dihydroisobenzofurans by the iodocyclization of 2-(1-alkynyl)benzylic alcohols.

Authors:  Raffaella Mancuso; Saurabh Mehta; Bartolo Gabriele; Giuseppe Salerno; William S Jenks; Richard C Larock
Journal:  J Org Chem       Date:  2010-02-05       Impact factor: 4.354

7.  Fe-catalyzed Decarbonylative Alkylative Spirocyclization of N-Arylcinnamamides: Access to Alkylated 1-Azaspirocyclohexadienones.

Authors:  Xiang Peng; Ren-Xiang Liu; Xiang-Yan Xiao; Luo Yang
Journal:  Molecules       Date:  2020-01-21       Impact factor: 4.411
  7 in total

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