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Synlett
Volumn , Issue 5, 2009, Pages 0735-0738
Domino reaction for the construction of new 2-oxo[1,2,4]triazolo[5,1- c][1,4]thiazines
Author keywords

1,2 diazabuta 1,3 dienes; 1,2,4 triazol 2 ones; 1,4 thiazines; Domino reaction; Michael addition
Indexed keywords

EID: 62349089620     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087928     Document Type: Article
Times cited : (4)
References (39)
  • 20
    • 62349103937 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of α-Thiohydrazone 1,4-Adducts 3a-m: To an ice-cooled solution of 1,2-diazabuta-1,3-diene 1a,b,i as a mixture of E/Z isomers (1.0 mmol) in CH 2Cl2 (5 mL, the 3-mercaptobutan-2-one 2a (1.1 mmol) or 3-mercaptopentan-2-one 2b (1.1 mmol) was added. The reaction was allowed to stir at r.t. for 4 h. The solvent was removed by rotary evaporation and the crude products were purified by crystallization for compound 3m or by flash column chromatography (silica gel, EtOAc) for compounds 3a,b,k,l to afford a-thiohydrazone 1,4-adducts derived from phosphine oxide and phosphonate-substituted 1,2-diazabuta-1,3-dienes. To obtain 3c-j, a stoichiometric amount of 1,2-diazabuta-1,3-dienes 1c-h (1.0 mmol) as a mixture of E/Z isomers26 was added to a solution of 3-mercaptobutan-2-one 2a (1.1 mmol) or 3-mercaptopentan-2-one 2b (1.1 mmol) in MeCN 20
    • 4PS: 446.1429; found: 446.1434.
  • 21
    • 62349121472 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of Mercapto Diketones 4a-e: To a solution of the α-thiohydrazone 3a,b,k,l,m (1.0 mmol) in MeCN (5 mL, Amberlyst 15H ion-exchange resin (50 mg) was added. The reaction was stirred at r.t. for 2 h. The solid was then filtered through a sintered glass vacuum filtration funnel. The filtrate was concentrated to dryness in vacuum. The crude products were purified by flash column chromatography (silica gel, EtOAc) to afford the corresponding mercapto diketones 4a-e. 3-[1-(Diphenylphosphoryl)-2-oxopropyl]sulfanylbutan-2-one (4a, isomeric mixture of the keto and enol tautomers; yield: 306 mg (85, obtained as a colorless oil as described in the general procedure. IR (film, 3435, 3046, 2921, 1705, 1431, 1362, 1197, 1117 cm-1. 1H NMR (300 MHz, CDCl3, δ, 0.94 (d, 3 H, 3JHH, 7.2 Hz, 1.24 (d, 3 H, 3JHH, 7.2 Hz, 1.82 s, 3 H, 1.91
    • 3PS: 360.0949; found: 360.0952.
  • 25
    • 62349135748 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of [1,2,4]Triazolo[5,1-c][1,4]thiazines 7a-h: To obtain [1,2,4]triazolo[5,1-c][1,4] thiazines 7b-h, the α-thiohydrazones 3d-j (1 mmol) were refluxed in MeCN for 26-48 h. To prepare compounds 7b-h directly, a stoichiometric amount of 1,2-diazabuta-1,3-dienes 1d-h (1 mmol) was added to a solution of 3-mercaptobutan-2-one 2a (1.1 mmol) or 3-mercaptopentan-2-one 2a (1.1 mmol) in MeCN (20 mL) with magnetic stirring at r.t. until the disappearance of the reagent, as evidenced by disappearance of typical red color of the 1,2-diazabuta-1,3-dienes 1. The crude was then refluxed for 26-48 h. In the case of 7a the hydrazone 3c (1 mmol) was refluxed for 28 h in the presence of a stoichiometric amount of Amberlyst 15H ion-exchange resin (1 mmol, After disappearance of the starting materials monitored by TLC, the reaction solvent was evaporated under reduced press
    • 3S: C, 46.68; H, 5.88; N, 16.33. Found: C, 46.82; H, 5.92; N, 16.19.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.