Synthesis of dispiropyrrolidines from chromone-3-carbaldehyde using sarcosine and ninhydrin as the source of an azomethine ylide

Synthesis and Chemical Reactivity of 4‐Oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde

“…Similar type of reaction observed in case of bischromone and N ‐methylglycine and gave 120 . On the other hand, ninhydrin and N ‐methylglycine gave spiro compounds 121 and 122 under similar condition due to the interaction between the C 2 –C 3 double bond of 1 and azomethine ylide formed in situ (Scheme ).…”

Chemistry and application of 4-oxo-4H-1-benzopyran-3-carboxaldehyde

“…226 Ninhydrin being far more reactive than ChrCHO forms with sarcosine the azomethine ylid 349 that adds to ChrCHO to give 351; the compound 350 arises through the reaction of 349 with in situ generated formaldehyde followed by interaction with 1. Addition of formalin in the reaction mixture produces 350 exclusively.…”

“…Addition of formalin in the reaction mixture produces 350 exclusively. 226 The piperazine 352 arises by dimerization of the ylid 349 (Scheme 34). Formation of the pyrrolo[2,1-a]isoquinoline by stirring a mixture of 1, isoquinoline and phenacyl bromide (or ethyl bromoacetate) in water containing a surfactant as CTAB and a base as DBU has been reported by Naskar and co-workers.…”

Ninhydrin in synthesis of heterocyclic compounds

“…190 Chromone-3-carbaldehydes 94 have been used as dipolarophiles in the one-pot synthesis of several dispirochromanopyrrolidines 95 and 96 as a racemic mixture in boiling alcohol (Scheme 26). 193 In a one-pot cycloaddition reaction, the azomethine ylide 87 was reacted with (E)5H-2- 195 The synthesized compounds in this study were screened for their antimycobacterial activities, with four of them showing good activity with MIC of less than 1 µM. The reaction of (Z)-16-arylmethylidene estrone derivatives 101 with 87 for the facile synthesis of hitherto unknown steroidal pyrrolidines 102 was described (Scheme 26).…”