Abstract:A novel, acid-catalysed cyclisation of salicylaldehyde thiosemicarbazones (1a±d) yields new 2H-benz[e]-1,3-oxazine-2thiones (2a±d) in a one-pot procedure.
“…Interestingly, this is the first example of the synthesis of 4-hydrazinobenzoxazinones 9 and their reductive dehydrazination to 10 . The key element in our approach is the novel utilization of salicylaldehyde as a bifunctional building block whose application to the construction of various benzo-fused oxygen heterocycles of chemical and biological interest is well documented. − …”
One-pot montmorillonite K-10 clay supported reactions of either salicylaldehyde/2-hydroxyacetophenone hydrazones and aryl-/alkylureas or salicylaldehydes/2-hydroxyacetophenone and 4-aryl-/alkylsemicarbazides expeditiously yield 3,4-dihydro-4-hydrazino-2H-benz[e]-1,3-oxazin-2-ones (9) via cycloisomerization of the intermediate salicylaldehyde/2-hydroxyacetophenone 4-aryl-/alkylsemicarbazones (5) under solvent-free microwave irradiation. Under the same conditions, hydrazines (9) readily underwent reductive dehydrazination on alumina-supported copper(II) sulfate to furnish 2H-benz[e]-1,3-oxazin-2-ones (10).
“…Interestingly, this is the first example of the synthesis of 4-hydrazinobenzoxazinones 9 and their reductive dehydrazination to 10 . The key element in our approach is the novel utilization of salicylaldehyde as a bifunctional building block whose application to the construction of various benzo-fused oxygen heterocycles of chemical and biological interest is well documented. − …”
One-pot montmorillonite K-10 clay supported reactions of either salicylaldehyde/2-hydroxyacetophenone hydrazones and aryl-/alkylureas or salicylaldehydes/2-hydroxyacetophenone and 4-aryl-/alkylsemicarbazides expeditiously yield 3,4-dihydro-4-hydrazino-2H-benz[e]-1,3-oxazin-2-ones (9) via cycloisomerization of the intermediate salicylaldehyde/2-hydroxyacetophenone 4-aryl-/alkylsemicarbazones (5) under solvent-free microwave irradiation. Under the same conditions, hydrazines (9) readily underwent reductive dehydrazination on alumina-supported copper(II) sulfate to furnish 2H-benz[e]-1,3-oxazin-2-ones (10).
“…Prompted by the above reports and in pursuing our work on new cyclization methods, [9][10][11] we have devised an expeditious and highly diastereoselective one-pot annulation of pyrimidine ring on azoles to give 4 using microwaves in catalyst-and solvent-free conditions (Scheme 1).…”
Azole Schiff bases 2a-f are annulated diastereoselectively with glycine and acetic anhydride, under microwave irradiation and solvent-free conditions, to yield 6,7-dihydro-5H-1,3,4oxa(thia)diazolo[3,2-a]pyrimidin-5-ones 4a-f in a one-pot procedure.
A Novel, One-Pot Synthesis of 2H-Benz[e]-1,3-oxazine-2-thiones. -A probable mechanism is given for the reaction. -(VADAV, LAL DHAR S.; SAIGAL, SANDHYA; PAL, DAYA R.; J.
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