Tandem cyclization-[3+3] cycloaddition reactions of 2-alkynylbenzaldoxime: synthesis of fused 1,2-dihydroisoquinolines

Tetrahedron Letters

Volumn 50, Issue 2, 2009, Pages 198-200

  Ding, Qiuping ^a,c   Wang, Zhiyong ^a   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

1,2 Dihydroisoquinoline; 2 Alkynylbenzaldoxime; Dimethyl cyclopropane 1,1 dicarboxylate; Silver triflate; Yetterbium triflate

Indexed keywords

1,2 DIHYDROISOQUINOLINE DERIVATIVE; 2 ALKYNYLBENZALDOXIME; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; ISOQUINOLINE DERIVATIVE; OXAZINE DERIVATIVE; OXIME DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; SYNTHESIS;

EID: 56949102619     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.10.121     Document Type: Article

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84. 3 (10 mol %) in toluene (2.0 mL) at 80 °C under nitrogen atmosphere. After 5 min, dimethyl cyclopropane-1,1-dicarboxylate (0.36 mmol, 1.2 equiv) was added. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to room temperature, quenched with water (10 mL), and extracted with EtOAc (2 × 10 mL). Evaporation of the solvent followed by purification of the residue on silica gel afforded fused 1,2-dihydroisoquinoline 3.