Synthesis of Novel Spiro Thiazolo[3,2‐a][1,3,5]triazines via 1,3‐Dipolar Cycloaddition of Azomethine Ylide

Abstract

The 1,3-dipolar cycloaddition of an azomethine ylide generated by a decarboxylative route from sarcosine and acenaphthenequinone to 7-arylmethylidene-3-aryl-3,4-dihydro-2H-thiazolo[3,2-a][1,3,5]triazin-6(7H)-ones afforded novel dispiro[acenaphthylene-1,2'-pyrrolidine]-3',7''-[1,3]thiazolo[3,2-a][1,3,5]triazines in moderate yields. The structures of the products were determined and characterized thoroughly by NMR, MS, IR, elemental analysis and X-ray crystallographic analysis. The results of experiment indicated that this 1,3-dipolar cycloaddition proceeded with high stereoselectivity and regioselectivity.

Synthesis of Novel Dispiro[Acenaphthylene-Pyrrolidine-Pyrrolisine] Derivatives via a 1,3-Dipolar Cycloaddition of Azomethine Ylide

“…10 The azomethine ylid generated in situ from acenaphthenequinone and sarcosine reacted with the (E)exocyclic double bond of the dipolarophile giving one product with the indicated stereochemistry. 10,11 Finally, the regio-and stereochemical outcomes of the cycloaddition reactions were unambiguously ascertained by single crystal X-ray analysis of cycloadducts 2b (Fig. 2).…”

Investigation of the Interaction Between Novel Spiro Thiazolo[3,2-a][1,3,5]Triazines and Bovine Serum Albumin by Spectroscopic Methods

“…Novel spiro thiazolo [3,2-a] [1,3,5]triazines were obtained according to the reported procedure [4] and the NSTT (1.00 9 10 -3 molÁL…”

“…Spiropyrrolidines are also motifs in some pharmacologically active alkaloids, such as rhynchophylline, corynoxeine, horsifiline, mitraphylline and spirotryprostatins [1][2][3][4].…”