Regioselective synthesis of novel spiropyrrolidines and spirothiapyrrolizidines through multicomponent 1,3-dipolar cycloaddition reaction of azomethine ylides.
A series of novel spiropyrrolidines and spirothiapyrrolizidines were synthesized via a three-component 1,3-dipolar cycloaddition reaction of isatin or acenaphthenequinone, sarcosine or thiaproline and 4-hydroxy-6-methyl-3-((E)-3-phenylacryloyl)-2H-pyran-2-ones in refluxing ethanol. Advantages of this method include the availability of starting materials, mild reaction conditions, high yields, and the complete regioselectivity observed.
Liu
Hai
H
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123, PR China.
Dou
Guolan
G
Shi
Daqing
D
D001391:Azo Compounds / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013882:Thiosemicarbazones / Q000737:chemistry*
D001391:Azo Compounds; D011759:Pyrrolidines; D013141:Spiro Compounds; D053778:Thiazolidines; D013882:Thiosemicarbazones; C512188:azomethine