Employment of Two-Acid Promoter System in Pictet–Spengler Reaction: A Robust Two-Step Synthesis of Aza-Heterocycles
The growing demand for increasingly sustainable chemical processes continues to stimulate organic chemistry to develop highly efficient, low-energy-consuming new reactions that require minimal effort to isolate intermediates and produce reduced waste. In this context, two-step reactions play an important role, and a good approach is the two-step synthesis, in which reagents and catalysts or promoters are introduced sequentially. Among these, the Pictet-Spengler-type cyclization (PS) is a powerful stepwise strategy for the synthesis of heterocyclic compounds. This article presents a novel and environmentally friendly two-step strategy for the Pictet-Spengler reaction, employing graphene oxide and Amberlyst 15 as acid promoters that yields a diverse product library (up to 92% yield) without the need for further purification. Both promoters can be reused over multiple reaction cycles, maintaining high efficiency. The methodology demonstrates broad functional group tolerance and provides a sustainable route to various tetrahydro-β-carbolines (THβCs), including biologically relevant compounds, and, above all, avoids negative interference between the two acidic promoters.
Authors
- Serena Gabrielli (ORCID: https://orcid.org/0000-0002-2048-5813)
- Cristina Cimarelli (ORCID: https://orcid.org/0000-0002-7289-0941)
- Gabriele Lupidi (ORCID: https://orcid.org/0000-0001-9891-0552)
- Dario Gentili (ORCID: https://orcid.org/0000-0001-9706-4219)
- Alessio Petrellini
- Federico Vittorio Rossi (ORCID: https://orcid.org/0000-0001-7739-3306)
- Enrico Marcantoni (ORCID: https://orcid.org/0000-0002-8686-3987)
- Vishnuprasad Ponnarassery Aravindakshan
- Francesco Catalini
- Alessandro Guzzini
- Giacomo Di Giambattista (ORCID: https://orcid.org/0009-0006-5561-9494)
Institutions
- Università di Camerino (IT)
- University of Perugia (IT)
Publication Details
- Journal
- ACS Omega
- Published
- 2026-02-16
- DOI
- https://doi.org/10.1021/acsomega.5c11423
- Primary Topic
- Synthesis and bioactivity of alkaloids
- Type
- article
- Field-Weighted Citation Impact
- 0.00