1,3-dipolar cycloadditions from tricyclic hemiaminals. Synthesis of the quinocarcin core through catalyst-free generation of azomethine ylides

Lena Huck; J Francisco González; Elena de la Cuesta; J Carlos Menéndez; Carmen Avendaño

doi:10.1039/c1ob05181d

1,3-dipolar cycloadditions from tricyclic hemiaminals. Synthesis of the quinocarcin core through catalyst-free generation of azomethine ylides

Org Biomol Chem. 2011 Sep 21;9(18):6271-7. doi: 10.1039/c1ob05181d. Epub 2011 Jul 19.

Authors

Lena Huck¹, J Francisco González, Elena de la Cuesta, J Carlos Menéndez, Carmen Avendaño

Affiliation

¹ Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, Madrid, Spain.

PMID: 21773620
DOI: 10.1039/c1ob05181d

Abstract

The generation of azomethine ylides from the readily accessible hemiaminals 3 and 8 or from iminium salt 10 was studied. Compounds 8 gave anti- and syn-cycloadducts containing the quinocarcin core through a catalyst-free dehydration process.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines / chemistry*
Azo Compounds / chemical synthesis*
Azo Compounds / chemistry
Cyclization
Imines / chemistry
Isoquinolines / chemical synthesis*
Isoquinolines / chemistry
Thiosemicarbazones / chemical synthesis*
Thiosemicarbazones / chemistry

Substances

Amines
Azo Compounds
Imines
Isoquinolines
Thiosemicarbazones
azomethine
quinocarcin