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Literature DB >> 12868929

Synthesis of isocoumarins and alpha-pyrones via electrophilic cyclization.

Abstract

A variety of substituted isocoumarins and alpha-pyrones are readily prepared in excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzoates and (Z)-2-alken-4-ynoates with ICl, I(2), PhSeCl, p-O(2)NC(6)H(4)SCl, and HI. This methodology accommodates various alkynyl esters and has been successfully extended to the synthesis of polycyclic aromatic and biaryl compounds.

Entities: Chemical Disease

Year: 2003 PMID： 12868929 DOI： 10.1021/jo034308v

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

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Cited

28 in total

1. Syntheses of isochromenes and naphthalenes by electrophilic cyclization of acetylenic arenecarboxaldehydes.

Authors: Dawei Yue; Nicola Della Ca; Richard C Larock
Journal: J Org Chem Date: 2006-04-28 Impact factor: 4.354

2. 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

3. 5,6-dihydro-2H-pyranones and 5,6-dihydro-2H-pyridones and their derivatives modulate in vitro human T lymphocyte function.

Authors: Y Baba Hamed; A Medjdoub; B Mostefa Kara; H Merzouk; D Villemin; M Narce
Journal: Mol Cell Biochem Date: 2011-08-30 Impact factor: 3.396

4. Pd/C-mediated synthesis of α-pyrone fused with a five-membered nitrogen heteroaryl ring: a new route to pyrano[4,3-c]pyrazol-4(1H)-ones.

Authors: Dhilli Rao Gorja; Venkateswara Rao Batchu; Ashok Ettam; Manojit Pal
Journal: Beilstein J Org Chem Date: 2009-11-11 Impact factor: 2.883

10. 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

Synthesis of isocoumarins and alpha-pyrones via electrophilic cyclization.

1. Syntheses of isochromenes and naphthalenes by electrophilic cyclization of acetylenic arenecarboxaldehydes.

2. 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.

3. 5,6-dihydro-2H-pyranones and 5,6-dihydro-2H-pyridones and their derivatives modulate in vitro human T lymphocyte function.

4. Pd/C-mediated synthesis of α-pyrone fused with a five-membered nitrogen heteroaryl ring: a new route to pyrano[4,3-c]pyrazol-4(1H)-ones.

5. A novel synthetic route to 3-sulfenyl- and 3-selenylindoles by n-Bu4NI-induced electrophilic cyclization.

6. Synthesis of 3,4-disubstituted 2H-benzopyrans through C-C bond formation via electrophilic cyclization.

7. Competition studies in alkyne electrophilic cyclization reactions.

8. Solution-phase synthesis of a diverse isocoumarin library.

9. The synthesis of highly substituted isoxazoles by electrophilic cyclization: an efficient synthesis of valdecoxib.

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