# Tandem Synthesis of Tetrahydropyrroloquinazolines and Related Polyannular Scaffolds

**Authors:** Haley M. Carlson, R. Adam Mosey

PMC · DOI: 10.1021/acs.joc.5c00996 · The Journal of Organic Chemistry · 2025-06-18

## TL;DR

A new method for efficiently creating complex chemical structures called tetrahydropyrroloquinazolines in a single reaction step.

## Contribution

A novel tandem synthesis approach that forms two heterocyclic rings in a single pot using an alkyl tether.

## Key findings

- The tandem synthesis successfully forms tetrahydropyrroloquinazolines from amino amides and aldehydes.
- The method allows for the creation of diverse fused cycloalkyl and bicyclic ring systems.
- The reaction can also produce the indoloquinazolinone scaffold.

## Abstract

A Tf2O-mediated tandem synthesis of tetrahydropyrroloquinazolines
from amino amides and aldehydes has been developed in which both heterocyclic
rings of the scaffold are assembled in a single pot. An alkyl tether
linking the amide and amine functionalities acts as a carbon bridge
to form saturated rings about the core amidine moiety, thereby facilitating
the installation of diverse fused cycloalkyl and bicyclic ring systems.
The reaction also extends to the formation of the indoloquinazolinone
scaffold.

## Linked entities

- **Chemicals:** Tf2O (PubChem CID 67749), aldehydes (PubChem CID 6449839)

## Full-text entities

- **Chemicals:** aldehydes (MESH:D000447), carbon (MESH:D002244), Tetrahydropyrroloquinazolines (-), O (MESH:D010100), amidine (MESH:D000578), amine (MESH:D000588), amide (MESH:D000577)

## Full text

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## Figures

11 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12235636/full.md

## References

13 references — full list in the complete paper: https://tomesphere.com/paper/PMC12235636/full.md

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Source: https://tomesphere.com/paper/PMC12235636