Preparation of 3-diazoindolin-2-imines via cascade reaction between indoles and sulfonylazides and their extensions to 2,3-diaminoindoles and imidazo[4,5-b]indoles.
Org Lett
; 16(19): 5096-9, 2014 Oct 03.
Article
in En
| MEDLINE
| ID: mdl-25211289
ABSTRACT
3-Diazoindolin-2-imines were constructed from indoles and sulfonylazides via an electronically matched 1,3-dipolar cycloaddition and a subsequent dehydroaromatization/ring-opening cascade. The reaction between 3-substituted indoles and sulfonyl azides provided 2-aminoindoles, while 2-substituted indoles furnished 3-aminoindoles. Moreover, 2,3-diaminoindoles could be prepared from the resulting 3-diazoindolin-2-imines and secondary amines via a rhodium-catalyzed amination. Further extension of 2,3-diaminoindoles led to the formation of imidazo[4,5-b]indoles.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Azides
/
Heterocyclic Compounds, 3-Ring
/
Imidazoles
/
Imines
/
Indoles
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2014
Document type:
Article