TY - JOUR

T1 - In situ generation of imines by the Staudinger/azaWittig tandem reaction combined with thermally induced Wolff rearrangement for one-pot threecomponent β-lactam synthesis

AU - Paramonova, Polina

AU - Lebedev, Rodion

AU - Bakulina, Olga

AU - Dar'in, Dmitry

AU - Krasavin, Mikhail

PY - 2022/11

Y1 - 2022/11

N2 - A new efficient protocol for diastereoselective three-component one-pot lactam synthesis involving the in situ generation of imines via the Staudinger/aza-Wittig tandem reaction combined with the Wolff-rearrangement and ketene–imine cycloaddition was developed to produce a series of 24 novel structurally diverse β-lactam- or 1,3-oxazine-products. It was shown that this synthesis can be performed both as a two step-procedure and true MCR with simultaneous loading of all reactants. The intramolecular version of the 1st step provided facile access to seven-membered cyclic imines, which allowed further preparation of a series of rare tricyclic β-lactams. For the intermolecular version of the 1st step (acyclic imine generation), it was shown that the outcome of the synthesis is different from that using pre-synthesized and isolated imines. Additionally, this is the first example of the implementation of the Staudinger/aza-Wittig tandem reaction for the preparation of four-membered heterocycles.

AB - A new efficient protocol for diastereoselective three-component one-pot lactam synthesis involving the in situ generation of imines via the Staudinger/aza-Wittig tandem reaction combined with the Wolff-rearrangement and ketene–imine cycloaddition was developed to produce a series of 24 novel structurally diverse β-lactam- or 1,3-oxazine-products. It was shown that this synthesis can be performed both as a two step-procedure and true MCR with simultaneous loading of all reactants. The intramolecular version of the 1st step provided facile access to seven-membered cyclic imines, which allowed further preparation of a series of rare tricyclic β-lactams. For the intermolecular version of the 1st step (acyclic imine generation), it was shown that the outcome of the synthesis is different from that using pre-synthesized and isolated imines. Additionally, this is the first example of the implementation of the Staudinger/aza-Wittig tandem reaction for the preparation of four-membered heterocycles.

U2 - https://doi.org/10.1039/D2OB01852G

DO - https://doi.org/10.1039/D2OB01852G

M3 - Article

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 48

ER -