Spiro heterocyclic compounds. IV. Synthesis of spiro[oxindole-3,4'-(2',3'-dihydro-4'H-pyran)] and spiro[oxindole-3,4'-(1',4'-dihydropyridine)] compounds.
Тип публикации: Journal Article
Дата публикации: 2011-12-08
SCImago Q3
WOS Q3
БС2
SJR: 0.318
CiteScore: 2.4
Impact factor: 1.5
ISSN: 00092363, 13475223
General Chemistry
Drug Discovery
General Medicine
Краткое описание
The Michael reaction of 3-(carboethoxy-cyano) methyleneoxindole (Ia) or 3-dicyanomethyleneoxindole (Ib) with active methyl groups, e.g., acetophenone and acetone, afforded, the corresponding normal Michael adducts (IIa-c). The reduction of IIa with NaBH4 gave the spiro [oxindole-3, 4'-(2', 3'-dihydro-4'H-pyran)] compound (III), which on reaction with diazomethane afforded two methoxy derivatives (IVa, b) diastereomeric at C-2' of the 2', 3'-dihydropyran ring. The reduction of IIb, c with NaBH4 gave similar spiro compounds (V-VI), which gave similar diastereoisomers, Va, b and VIa, b, respectively. Refluxing of IIc with NH2OH gave the spiro [oxindole-3, 4'-(1', 4'-dihydropyridine)] compound (X). When the same reaction was carried out at 0°, compound (IX), the precursor of X, was obtained.
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Higashiyama K., OTOMASU H. Spiro heterocyclic compounds. IV. Synthesis of spiro[oxindole-3,4'-(2',3'-dihydro-4'H-pyran)] and spiro[oxindole-3,4'-(1',4'-dihydropyridine)] compounds. // Chemical and Pharmaceutical Bulletin. 2011. Vol. 28. No. 5. pp. 1540-1545.
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Higashiyama K., OTOMASU H. Spiro heterocyclic compounds. IV. Synthesis of spiro[oxindole-3,4'-(2',3'-dihydro-4'H-pyran)] and spiro[oxindole-3,4'-(1',4'-dihydropyridine)] compounds. // Chemical and Pharmaceutical Bulletin. 2011. Vol. 28. No. 5. pp. 1540-1545.
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TY - JOUR
DO - 10.1248/cpb.28.1540
UR - https://doi.org/10.1248/cpb.28.1540
TI - Spiro heterocyclic compounds. IV. Synthesis of spiro[oxindole-3,4'-(2',3'-dihydro-4'H-pyran)] and spiro[oxindole-3,4'-(1',4'-dihydropyridine)] compounds.
T2 - Chemical and Pharmaceutical Bulletin
AU - Higashiyama, Kimio
AU - OTOMASU, Hirotaka
PY - 2011
DA - 2011/12/08
PB - Pharmaceutical Society of Japan
SP - 1540-1545
IS - 5
VL - 28
SN - 0009-2363
SN - 1347-5223
ER -
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@article{2011_Higashiyama,
author = {Kimio Higashiyama and Hirotaka OTOMASU},
title = {Spiro heterocyclic compounds. IV. Synthesis of spiro[oxindole-3,4'-(2',3'-dihydro-4'H-pyran)] and spiro[oxindole-3,4'-(1',4'-dihydropyridine)] compounds.},
journal = {Chemical and Pharmaceutical Bulletin},
year = {2011},
volume = {28},
publisher = {Pharmaceutical Society of Japan},
month = {dec},
url = {https://doi.org/10.1248/cpb.28.1540},
number = {5},
pages = {1540--1545},
doi = {10.1248/cpb.28.1540}
}
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Higashiyama, Kimio, and Hirotaka OTOMASU. “Spiro heterocyclic compounds. IV. Synthesis of spiro[oxindole-3,4'-(2',3'-dihydro-4'H-pyran)] and spiro[oxindole-3,4'-(1',4'-dihydropyridine)] compounds..” Chemical and Pharmaceutical Bulletin, vol. 28, no. 5, Dec. 2011, pp. 1540-1545. https://doi.org/10.1248/cpb.28.1540.
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