Nitrile stabilized synthesis of pyrrolidine and piperidine derivatives <i>via</i> tandem alkynyl aza-Prins–Ritter reactions

Shit, Sudip; Choudhury, Chinmayee; Saikia, Anil K.

doi:10.1039/d3ob01764h

Org. Biomol. Chem.

2024

DOI: 10.1039/d3ob01764h

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Nitrile stabilized synthesis of pyrrolidine and piperidine derivatives via tandem alkynyl aza-Prins–Ritter reactions

Sudip Shit,

Chinmayee Choudhury,

Anil K. Saikia

Abstract: Triflic acid-mediated protocol for the synthesis of N-(pyrrolidine-3-ylidenemethyl)acetamide and its piperidine analogue in good yields with separable Z/E isomer has been demonstrated.

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An Acid Catalyzed Alkynyl‐Prins Cyclization‐Rearrangement Cascade of 2‐(Alkynol)Benzoates: An Approach to 3‐Alkyl‐[n,5]‐Oxaspirophthalides

Mishra,

Baire

2024

Adv Synth Catal

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The oxaspiro‐phthalides ([n,5]‐oxaspirobenzalactones) bearing a phthalide spirofused to a cyclic‐ether of various sizes are frameworks found in bioactive natural products. The discovery and development of an alkynyl‐Prins cyclization based, strategy for the construction of structurally interesting, medicinally useful [5,5]‐ [6,5]‐, and [7,5]‐oxaspirophthalides is reported in this manuscript. Our strategy may represent the first report on the construction of oxaspiro‐phthalides using the alkynyl‐Prins cyclization. This approach exhibits broad substrate scope with respect to carbonyl compounds and 2‐(alkynol)benzoates, with yields ranging between 71‐98%. Isolation of intermediate, and further conversion of it to the end‐product supported the proposed mechanistic pathway.

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An Acid Catalyzed Alkynyl‐Prins Cyclization‐Rearrangement Cascade of 2‐(Alkynol)Benzoates: An Approach to 3‐Alkyl‐[n,5]‐Oxaspirophthalides

Mishra,

Baire

2024

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

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Nitrile stabilized synthesis of pyrrolidine and piperidine derivatives via tandem alkynyl aza-Prins–Ritter reactions

Abstract: Triflic acid-mediated protocol for the synthesis of N-(pyrrolidine-3-ylidenemethyl)acetamide and its piperidine analogue in good yields with separable Z/E isomer has been demonstrated.

Cited by 1 publication

References 37 publications

An Acid Catalyzed Alkynyl‐Prins Cyclization‐Rearrangement Cascade of 2‐(Alkynol)Benzoates: An Approach to 3‐Alkyl‐[n,5]‐Oxaspirophthalides

An Acid Catalyzed Alkynyl‐Prins Cyclization‐Rearrangement Cascade of 2‐(Alkynol)Benzoates: An Approach to 3‐Alkyl‐[n,5]‐Oxaspirophthalides

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