2‐(Het)aryl‐N‐phosphorylpyrrolidines via Cyclization of Phosphorus Acid Amides: A Regioselective Approach. Issue 39 (16th October 2020)

• Record Type: Journal Article
• Authors: Smolobochkin, Andrey V.; Turmanov, Rakhymzhan A.; Abdullaeva, Dinara S.; Gazizov, Almir S.; Voronina, Julia K.; Appazov, Nurbol O.; Buzyurova, Daina N.; Burilov, Alexander R.; Pudovik, Michail A.
• Is Part Of: ChemistrySelect. Volume 5:Issue 39(2020)
• Page Start: 12045
• Page End: 12050
• Publication Date: 2020-10-16
• Subjects: Cyclization -- Nitrogen heterocycles -- Phosphorus amides -- Pyrrolidines -- Synthetic methods; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202003353
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A first successful synthesis of 2‐(het)aryl‐ N ‐phosphorylpyrrolidines is reported starting from readily available N ‐(4, 4‐diethoxybutyl)amides of P(V) acids. A range of phenols and hydroxyl‐substituted O ‐heterocycles may be employed into the reaction furnishing N ‐phosphorylated 2‐(het)arylpyrrolidines with up to 90 % yield. The developed method permits a presence of sensitive to phosphorylation hydroxy groups and provides the easy and regioselective entry to target compounds. Abstract : A one‐pot synthesis of various 2‐(het)aryl‐ N ‐phosphorylpyrrolidines is reported. The proposed approach relies on intramolecular cyclisation / electrophilic substitution of readily available N ‐(4, 4‐diethoxybutyl)amides of P(V) acids. The presence of phosphorylation‐sensitive groups in a substrate does not interfere with the reaction, thus allowing regioselective synthesis of hitherto unknown N ‐phosphorylpyrrolidines possessing hydroxy(het)aryl moiety.