Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide – a versatile building block for the synthesis of new thiopyran-based heterocyclic systems

Abstract

Three series of new cyclic sulfones have been prepared by a one-pot multi-component reactions.

First Synthesis of 2-Amino-5-hydroxy-4H-chromene-3-carbonitriles from 4-(2-Pyridylazo)resorcinol

“…Possible products of the reaction of PAR with aldehydes and malononitrile with the expected structure of 6-(2-pyridylazo)-4H-chromenes are promising as new metallochromic indicators, reagents for the extraction of heavy metals from the organic phase, or as biologically active compounds by analogy with the available data [18,34,35]. In continuation of our studies in the chemistry of 4H-pyrans and 4H-chromenes [36][37][38][39], herein we reported the possibility of using PAR in organic synthesis, and in particular, for the preparation of 2-amino-4H-chromene-3-carbonitriles.…”

2-Amino-4,6,7,8-tetrahydrothiopyrano[3,2-b]pyran-3-carbonitrile 5,5-dioxide VP-4535 as an antimicrobial agent selective toward methicillin‐resistant Staphylococcus aureus

“…chemistry. We have recently found that compound 1 easily reacts with aromatic aldehydes and malononitrile in a 1:1:1 molar ratio in EtOH in the presence of catalytic amounts of piperidine to give bicyclic products 2 in very good yields (64-91%) [33]…”

Recent applications of ninhydrin in multicomponent reactions

“…A new spiro thiopyrano pyran derivative 74 has been prepared by Palchykov and co-workers with the help of dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide 73, ninhydrin 1 and malononitrile 62 (Scheme 26). 103 The high reactivity of ketosulfone 73 was exploited to afford the desired product within a short reaction time. Azizian et al pioneered a concise green method for the synthesis of spiroindeno oxathiazine derivatives 76 by the onepot three component condensation of tetramethyl guanidine 74, ninhydrin 1 and isothiocyanates 75.…”