A Highly Efficient Copper(I)-Catalyzed Cascade Reaction of o-Alkenylphenyl Isothiocyanates with Isocyanides Leading to 5H-Benzo[d]imidazo[5,1-b][1,3]thiazines

The highly efficient copper(I)‐catalyzed cascade reaction of (E)‐3‐(2‐isothiocyanatophenyl)acrylates and (E)‐3‐(2‐isothiocyanatophenyl)acrylonitriles with isocyanides was explored. The method provides an expedient route for the synthesis of 5H‐benzo[d]imidazo[5,1‐b][1,3]thiazines in good to excellen...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2015-10, Vol.2015 (30), p.6655-6660
Main Authors: Hao, Wenyan, Huang, Jian, Jie, Shanshan, Cai, Mingzhong
Format: Article
Language:English
Subjects:
Copper
Domino reactions
Isocyanides
Isothiocyanates
Nitrogen heterocycles
Sulfur heterocycles
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The highly efficient copper(I)‐catalyzed cascade reaction of (E)‐3‐(2‐isothiocyanatophenyl)acrylates and (E)‐3‐(2‐isothiocyanatophenyl)acrylonitriles with isocyanides was explored. The method provides an expedient route for the synthesis of 5H‐benzo[d]imidazo[5,1‐b][1,3]thiazines in good to excellent yields by using CuCl (10 mol‐%) as the catalyst and K3PO4 (2.0 equiv.) as the base in THF at 70 °C. The reaction involves [3+2] cycloaddition and subsequent intramolecular C–S bond formation. The tandem addition–cyclization reaction of (E)‐3‐(2‐isothiocyanatophenyl)acrylates and (E)‐3‐(2‐isothiocyanatophenyl)acrylonitriles with isocyanides is described. This method offers an expedient route for the synthesis of 5H‐benzo[d]imidazo[5,1‐b][1,3]thiazines in good to excellent yields. The reaction involves [3+2] cycloaddition and subsequent intramolecular C–S bond formation.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500800