- 6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidenoacetonitrile in some fusion reactions
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6,7-Dimethoxy-3,4-dihydroisoquinolin-1-ylacetonitrile in the enamine form readily reacts with acyl iso(thio)cyanates affording in high yields 1,2-fused oxo- and thioxodihydropyrimidoisoquinolines and thiouracyloisoquinolines. The reaction of the enamine with primary amines of diverse classes in the presence of 2 equiv of formaldehyde resulted in 1,2-fused N-substituted tetrahydropyrimidinoisoquinolines whose yields depended on the basicity and sterical accessibility of the reagent. Fused 5-hydroxyindolo-, dioxopyrrolo-, pyrroloisoquinolines formed in medium yields in the one-stage reactions of the enamine with p-benzoquinone, oxalyl chloride, and β-nitrostyrene respectively. The reaction of 1-cyanomethyl-6,7-dimethoxydihydroisoquinoline with acrylonitrile leads to the formation of 1,2-fused iminopyridinoisoquinoline easily hydrolysable to pyridine derivative and readily reacting by the amidine group with aroyl chlorides and arylsulfonyl chlorides. Pleiades Publishing, Ltd., 2011.
- Afon'kin,Kostrikin,Shumeiko,Popov
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experimental part
p. 731 - 745
(2011/08/22)
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- Reactions of 1,2,3,4-Tetrahydroisoquinoline Derivatives with Sulfur
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1,2,3,4-Tetrahydroisoquinolines react with sulfur in pyridine to give two different types of products, depending on the structure of the starting compounds. 1-Substituted derivatives 1 undergo partial dehydrogenation with formation of the corresponding 3,4-dihydroisoquinolines 3. 1,2,3,4-Tetrahydroisoquinolines 5 bearing no substituent in 1-position yield the 3,4-dihydro-1(2H)isoquinolinethiones 6, comprising a new and simple synthesis of compounds 6.
- Ajzert, Ilona K.,Takacs, Kalman
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p. 1061 - 1064
(2007/10/02)
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