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.

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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
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article

Employment of Two-Acid Promoter System in Pictet–Spengler Reaction: A Robust Two-Step Synthesis of Aza-Heterocycles

Serena Gabrielli, Cristina Cimarelli, Gabriele Lupidi, Dario Gentili et al.
ACS Omega
Synthesis and bioactivity of alkaloids
article

Employment of Two-Acid Promoter System in Pictet–Spengler Reaction: A Robust Two-Step Synthesis of Aza-Heterocycles

Serena Gabrielli, Cristina Cimarelli, Gabriele Lupidi, Dario Gentili, Alessio Petrellini, Federico Vittorio Rossi, Enrico Marcantoni, Vishnuprasad Ponnarassery Aravindakshan, Francesco Catalini, Alessandro Guzzini, Giacomo Di Giambattista
article en

Abstract

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.

ACS OmegaVol. 11(8)
Università di Camerino (IT), University of Perugia (IT)
Responsible consumption and production
Openalex Percentile: Top 54%
Synthesis and bioactivity of alkaloids
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Employment of Two-Acid Promoter System in Pictet–Spengler Reaction: A Robust Two-Step Synthesis of Aza-Heterocycles — Serena Gabrielli, Cristina Cimarelli, et al. · ACS Omega (2026) | TGRS Research Map | TGRS