Novel routes to 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines and 5,6,9,10,11,11a-hexahydro-8H-pyrido[1,2-a]pyrrolo[2,1-c]pyrazines

Alan R Katritzky; Ritu Jain; Yong-Jiang Xu; Peter J Steel

doi:10.1021/jo020371t

Novel routes to 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines and 5,6,9,10,11,11a-hexahydro-8H-pyrido[1,2-a]pyrrolo[2,1-c]pyrazines

J Org Chem. 2002 Nov 15;67(23):8220-3. doi: 10.1021/jo020371t.

Authors

Alan R Katritzky¹, Ritu Jain, Yong-Jiang Xu, Peter J Steel

Affiliation

¹ Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu

PMID: 12423155
DOI: 10.1021/jo020371t

Abstract

Condensation reactions of benzotriazole and 2-(pyrrol-1-yl)-1-ethylamine (1) with formaldehyde and glutaric dialdehyde, respectively, afforded intermediates 2 and 6. Subsequent nucleophilic substitutions of the benzotriazole group in 2 and 6 with Grignard reagents, sodium cyanide, and sodium borohydride gave 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines 3a-e, 4, 5 and 5,6,9,10,11,11a-hexahydro-8H-pyrido[1,2-a]pyrrolo[2,1-c]pyrazines 7a-c, 8, 9, respectively, in good yields.

MeSH terms

Molecular Structure
Pyrazines / chemical synthesis*
Pyrazines / chemistry
Pyrrolidines / chemical synthesis
Pyrrolidines / chemistry
Stereoisomerism
Triazoles / chemistry

Substances

Pyrazines
Pyrrolidines
Triazoles
benzotriazole