Supramolecular aminocatalysis via inclusion complex: Amino-doped β-cyclodextrin as an efficient supramolecular catalyst for the synthesis of chromeno pyrimido[1,2-b]indazol in water

• Published in: Journal of industrial and engineering chemistry (Seoul, Korea) Vol. 68; pp. 6 - 13
• Main Authors: Shinde, Vijay Vilas, Jeong, Daham, Jung, Seunho
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 25.12.2018; 한국공업화학회
• Subjects: 2D ROESY NMR; Amino-appended supramolecular catalyst; Mono-6-deoxy-6-amino-β-cyclodextrin; One-pot synthesis; Poly heterocycles; 화학공학; One-pot synthesis; Mono-6-deoxy-6-amino-β-cyclodextrin; Poly heterocycles; Amino-appended supramolecular catalyst; 2D ROESY NMR
• ISSN: 1226-086X; 1876-794X
• DOI: 10.1016/j.jiec.2018.08.010

[Display omitted] •Amino-appended β-cyclodextrin (AA-β-CD) as a supramolecular organic base catalyst were synthesized.•AA-β-CD catalyzed the synthesis of chromeno pyrimido[1,2-b]indazol derivatives.•AA-β-CD as a catalyst can be easily recovered and reused.•Reaction mechanism was elucidated extensively by spectroscopic analysis. Well-modified amino-appended β-cyclodextrin (AA-β-CD) with an amino group at the primary face of the β-CD was synthesized and used in the catalytic synthesis of chromeno pyrimido[1,2-b]indazol as supramolecular catalysts in water for the first time. AA-β-CD was characterized by FT-IR, NMR, MALDI-TOF mass spectrometry, and SEM analysis. A possible reaction mechanism featuring molecular complexation was suggested based on 2D NMR (ROESY) spectroscopy, FE-SEM, DSC, and FT-IR. Advantages such as operational simplicity, recyclability of the catalysts, and accessibility in aqueous medium render this protocol eco-friendly.