Diastereoselective Synthesis of (Z)‐6‐(2‐Oxo‐1,2‐dihydro‐3H‐indol‐3‐ylidene)‐3,3a,9,9a‐tetrahydroimidazo[4,5‐e]thiazolo[3,2‐b]‐1,2,4‐triazin‐2,7(1H,6H)‐diones

Diastereoselective Synthesis of (Z)‐6‐(2‐Oxo‐1,2‐dihydro‐3H‐indol‐3‐ylidene)‐3,3a,9,9a‐tetrahydroimidazo[4,5‐e]thiazolo[3,2‐b]‐1,2,4‐triazin‐2,7(1H,6H)‐diones Full article

Journal

Journal of Heterocyclic Chemistry
ISSN: 0022-152X , E-ISSN: 1943-5193

Output data

Year: 2014, Volume: 51, Number: 4, Pages: 921-926 Pages count : 6 DOI: 10.1002/jhet.2008

Authors

Gazieva Galina A. ¹ , Shishkova Ekaterina A. ¹ , Kulikova Ludmila B. ¹ , Kolotyrkina Natal'ya G. ¹ , Sigay Natal'ya V. ¹ , Kravchenko Angelina N. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russian Federation

Two efficient and diastereoselective procedures for the synthesis of (Z)-6-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)-3,3a,9,9a-tetrahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazin-2,7(1H,6H)-diones by aldol-crotonic condensation of 1,3-dimethyl-3a,9a-diphenyl-3,3a,9,9a-tetrahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazin-2,7(1H,6H)-dione with isatins under acidic or basic catalysis are reported. Isomerization in (Z)-7-(1-allyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-1,3-dimethyl-3a,9a-diphenyl-1,3a,4,9a-tetrahydroimidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazin-2,8(3H,7H)-dione was observed under basic conditions.

Gazieva G.A. , Shishkova E.A. , Kulikova L.B. , Kolotyrkina N.G. , Sigay N.V. , Kravchenko A.N.
Diastereoselective Synthesis of (Z)‐6‐(2‐Oxo‐1,2‐dihydro‐3H‐indol‐3‐ylidene)‐3,3a,9,9a‐tetrahydroimidazo[4,5‐e]thiazolo[3,2‐b]‐1,2,4‐triazin‐2,7(1H,6H)‐diones
Journal of Heterocyclic Chemistry. 2014. V.51. N4. P.921-926. DOI: 10.1002/jhet.2008 WOS Scopus OpenAlex

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