A Green Approach to 2-Amino-4H-chromenes by Calcium Lactate Catalyzed, One-Pot, Three-Component Reactions

Sudipta Roy; Gitumoni Kalita; Satyapriya Maharana; Arunima Chatterjee; Rathin Jana; Naba K. Nath; Paresh Nath Chatterjee

doi:10.1055/s-0043-1775496

Synlett, Table of Contents

Synlett
DOI: 10.1055/s-0043-1775496

letter

Small Molecules in Medicinal Chemistry

A Green Approach to 2-Amino-4H-chromenes by Calcium Lactate Catalyzed, One-Pot, Three-Component Reactions

Sudipta Roy

^aDepartment of Chemical and Biological Sciences, National Institute of Technology Meghalaya, Saitsohpen Sohra, East Khasi Hills, Meghalaya 793108, India

^bTCG Lifesciences Pvt. Ltd., Block BN, Plot 7, Salt Lake Electronic Complex, Sector-V, Kolkata 700091, West Bengal, India

,

Gitumoni Kalita

^aDepartment of Chemical and Biological Sciences, National Institute of Technology Meghalaya, Saitsohpen Sohra, East Khasi Hills, Meghalaya 793108, India

,

Satyapriya Maharana

^aDepartment of Chemical and Biological Sciences, National Institute of Technology Meghalaya, Saitsohpen Sohra, East Khasi Hills, Meghalaya 793108, India

,

Arunima Chatterjee

^bTCG Lifesciences Pvt. Ltd., Block BN, Plot 7, Salt Lake Electronic Complex, Sector-V, Kolkata 700091, West Bengal, India

,

Rathin Jana

^cDepartment of Chemistry, Shahid Matangini Hazra Government General Degree College for Women, Chaksrikrishnapur, Kulberia, West Bengal 721649, India

,

Naba K. Nath∗

^aDepartment of Chemical and Biological Sciences, National Institute of Technology Meghalaya, Saitsohpen Sohra, East Khasi Hills, Meghalaya 793108, India

,

Paresh Nath Chatterjee∗

^dDepartment of Chemistry, National Institute of Technology Durgapur, Mahatma Gandhi Avenue, Durgapur 713209, West Bengal, India

› Author Affiliations

Abstract

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Abstract

A simple ecofriendly protocol for synthesizing 2-amino-4H-chromenes by a one-pot, three-component reaction catalyzed by nontoxic calcium lactate in a green solvent is described. 2-Amino-4H-chromene-3-carbonitriles are obtained by a one-pot, three-component reaction of an aromatic aldehyde, malononitrile, and a phenolic compound. Naphthopyrans are synthesized by the same strategy by replacing the phenolic derivative with a naphthol. Indole-substituted 2-amino-4H-chromenes are prepared by the one-pot three-component reaction of a salicylaldehyde derivative, a malononitrile derivative, and an indole.

Key words

calcium lactate catalysis - multicomponent reaction - chromenes - benzopyrans - green chemistry - indolylchromenes

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References

References and Notes

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21 2-Amino-7-hydroxy-4-phenyl-4H-chromene-3-carbonitrile (4a); Typical Procedure A 25 mL round-bottomed flask equipped with a magnetic stirrer bar was charged with benzaldehyde (1a; 1.0 mmol), malononitrile (2a; 1.2 mmol), resorcinol (3a; 1.0 mmol), and EtOH–H₂O (1:1, 5 mL). Calcium lactate (20 mol%) was added, and the flask was placed in a constant-temperature oil bath at 80 °C until the reaction was complete (TLC). The mixture was then filtered through a celite bed, which was thoroughly washed with EtOH. The combined filtrate was concentrated under reduced pressure, and the crude product was purified by flash chromatography (CombiFlash; silica gel, 20–50% EtOAc–hexane) to give an off-white solid; yield: 85%; mp 234 °C. ¹H NMR (400 MHz, DMSO-d₆ ): δ = 9.68 (s, 1 H), 7.30 (t, J = 7.5 Hz, 2 H), 7.15–7.21 (m, 3 H), 6.86 (br, 2 H), 6.79 (d, J = 8.4 Hz, 1 H), 6.46–6.48 (dd, J = 8.4 and 2.08 Hz, 1 H), 6.40 (d, J = 2.16 Hz, 1 H), 4.61 (s, 1 H). ¹³C NMR (100 MHz, DMSO-d₆ ): δ = 160.2, 157.0, 148.8, 146.3, 129.8, 128.5, 127.3, 126.6, 120.6, 113.7, 112.3, 102.1, 56.2, 39.9.

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