TY - JOUR

T1 - Reaction of Pyrrolobenzothiazines with Schiff Bases and Carbodiimides: Approach to Angular 6/5/5/5-Tetracyclic Spiroheterocycles

AU - Lystsova, Ekaterina A.

AU - Novokshonova, Anastasia D.

AU - Khramtsov, Pavel V.

AU - Novikov, Alexander S.

AU - Dmitriev, Maksim V.

AU - Maslivets, Andrey N.

AU - Khramtsova, Ekaterina E.

PY - 2024/5/1

Y1 - 2024/5/1

N2 - 1 H-Pyrrole-2,3-diones, fused at [ e]-side with a heterocycle, are suitable platforms for the synthesis of various angular polycyclic alkaloid-like spiroheterocycles. Recently discovered sulfur-containing [ e]-fused 1 H-pyrrole-2,3-diones (aroylpyrrolobenzothiazinetriones) tend to exhibit unusual reactivity. Based on these peculiar representatives of [ e]-fused 1 H-pyrrole-2,3-diones, we have developed an approach to an unprecedented 6/5/5/5-tetracyclic alkaloid-like spiroheterocyclic system of benzo[ d]pyrrolo[3',4':2,3]pyrrolo[2,1- b]thiazole via their reaction with Schiff bases and carbodiimides. The experimental results have been supplemented with DFT computational studies. The synthesized alkaloid-like 6/5/5/5-tetracyclic compounds have been tested for their biotechnological potential as growth stimulants in the green algae Chlorella vulgaris.

AB - 1 H-Pyrrole-2,3-diones, fused at [ e]-side with a heterocycle, are suitable platforms for the synthesis of various angular polycyclic alkaloid-like spiroheterocycles. Recently discovered sulfur-containing [ e]-fused 1 H-pyrrole-2,3-diones (aroylpyrrolobenzothiazinetriones) tend to exhibit unusual reactivity. Based on these peculiar representatives of [ e]-fused 1 H-pyrrole-2,3-diones, we have developed an approach to an unprecedented 6/5/5/5-tetracyclic alkaloid-like spiroheterocyclic system of benzo[ d]pyrrolo[3',4':2,3]pyrrolo[2,1- b]thiazole via their reaction with Schiff bases and carbodiimides. The experimental results have been supplemented with DFT computational studies. The synthesized alkaloid-like 6/5/5/5-tetracyclic compounds have been tested for their biotechnological potential as growth stimulants in the green algae Chlorella vulgaris.

KW - 1H-pyrrole-2,3-dione

KW - Chlorella

KW - DFT calculations

KW - Schiff base

KW - carbodiimide

KW - nitrogen heterocycle

KW - sulfur heterocycle

UR - https://www.mendeley.com/catalogue/2c64144b-cb8d-31a3-b252-45b36e6d8512/

U2 - 10.3390/molecules29092089

DO - 10.3390/molecules29092089

M3 - Article

C2 - 38731580

VL - 29

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 9

M1 - 2089

ER -