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| Main Authors: | , , , , , |
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| Format: | Artículo Open Access |
| Published: |
Wiley
2026
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| Subjects: | |
| Online Access: | https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cssc.70642 |
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Table of Contents:
- Mechanochemical Tandem Reactions: A Sustainable and Direct Route to 1,2‐Di‐Functional Indolizines via In Situ Baylis–Hillman Reaction, Cyclocondensation, Electrophilic C–H Chalcogenocyanation Soumik Saha Shravya B. Truptesh T. Mulgaonkar Saurav Bhattacharya Amrita Chatterjee Mainak Banerjee ChemSusChem Herein, we report a sustainable, metal‐free tandem mechanochemical strategy for the construction and C–H chalcogenocyanation of indolizines from pyridine‐2‐carboxaldehydes and α,β‐unsaturated compounds. The method involves DABCO‐catalyzed in situ formation of the Baylis–Hillman adduct followed by cyclization, delivering 2‐functionalized indolizines within 30 min under solid‐phase mixer‐milling conditions, with yields of up to 81%. Several of these products were further subjected to mechanochemical thio‐ and seleno‐cyanation. Notably, a combination of commercially available NaSCN/KSeCN and NCS first generates electrophilic chalcogenocyanating agents that afford the unprecedented 1‐chalcogenocyanated‐2‐formyl‐indolizine scaffold in just 15 min with up to 94% yields, in a work‐up‐free process. Interestingly, silica‐assisted solid‐phase mechanochemistry enables tandem conversion of the starting pyridine‐2‐carboxaldehydes and enones directly into 1,2‐difunctionalized indolizines, with practically no drop in overall yields (best yield 75%). Furthermore, the dual‐functional handles allow diverse post‐functionalizations, including the conversion of –SCN to –SCF 3 and sulfenyl tetrazoles, and –CHO to indolizino‐benzazoles, all via mixer‐milling. The scalability of the tandem mechanosynthesis of 1,2‐difunctionalized indolizines was established using selected examples. The time‐efficient and step‐economic solid‐phase tandem mechanochemical method exhibits strong sustainability metrics, including low process mass intensity (PMI 9.1 g g −1 ), low E‐factors (4.1), good atom economy (65% AE), and a high EcoScale score (∼70). 10.1002/cssc.70642 http://onlinelibrary.wiley.com/termsAndConditions#vor