An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy

An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy Full article

Journal

Beilstein Journal of Organic Chemistry
ISSN: 2195-951X , E-ISSN: 1860-5397

Output data

Year: 2016, Volume: 12, Pages: 2240-2249 Pages count : 10 DOI: 10.3762/bjoc.12.216

Authors

Izmest’ev Alexei N. ¹ , Gazieva Galina A. ¹ , Sigay Natalya V. ¹ , Serkov Sergei A. ¹ , Karnoukhova Valentina A. ² , Kachala Vadim V. ¹ , Shashkov Alexander S. ¹ , Zanin Igor E. ³ , Kravchenko Angelina N. ¹ , Makhova Nina N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str., 28, Moscow 119991, Russian Federation
3	Voronezh State University, Universitetskaya Pl., 1, Voronezh 394000, Russian Federation

An effective and highly regio- and diastereoselective one-pot method for the synthesis of new polynuclear dispiroheterocyclic systems with five stereogenic centers (dispiro[imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-6,3′-pyrrolidine-2′,3′′-indoles]) comprising pyrrolidinyloxindole and imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine moieties has been developed. The method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatin derivatives and sarcosine to 6-benzylideneimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7-diones.

Izmest’ev A.N. , Gazieva G.A. , Sigay N.V. , Serkov S.A. , Karnoukhova V.A. , Kachala V.V. , Shashkov A.S. , Zanin I.E. , Kravchenko A.N. , Makhova N.N.
An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy
Beilstein Journal of Organic Chemistry. 2016. V.12. P.2240-2249. DOI: 10.3762/bjoc.12.216 WOS Scopus OpenAlex

≡ Web of science:	WOS:000385896300001
≡ Scopus:	2-s2.0-84994417383
≡ OpenAlex:	W2533713205