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Titolo:
Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride
Autore:
Hiroya, K; Jouka, R; Kameda, M; Yasuhara, A; Sakamoto, T;
Indirizzi:
Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan Tohoku Univ Sendai Miyagi Japan 9808578 Ku, Sendai, Miyagi 9808578, Japan
Titolo Testata:
TETRAHEDRON
fascicolo: 48, volume: 57, anno: 2001,
pagine: 9697 - 9710
SICI:
0040-4020(20011126)57:48<9697:CRO2AA>2.0.ZU;2-S
Fonte:
ISI
Lingua:
ENG
Soggetto:
PALLADIUM-CATALYZED HETEROANNULATION; HETEROAROMATIC RING-SYSTEMS; CARBON TRIPLE BOND; TERMINAL ALKYNES; (Z)-3-ARYL(ALKYL)IDENE ISOINDOLIN-1-ONES; 3-SUBSTITUTED ISOCOUMARINS; INTRAMOLECULAR CYCLIZATION; STEREOSELECTIVE SYNTHESIS; O-ALKYNYLPHENOLS; ACETYLENES;
Keywords:
TBAF; 5-exo-dig; 6-endo-dig; isobenzofurans; benzopyrans; cyclization reactions;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
43
Recensione:
Indirizzi per estratti:
Indirizzo: Hiroya, K Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan Tohoku Univ Sendai Miyagi Japan 9808578 , Miyagi 9808578, Japan
Citazione:
K. Hiroya et al., "Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride", TETRAHEDRON, 57(48), 2001, pp. 9697-9710

Abstract

The regioselectivity of the cyclization reaction of 2-ethynylbenzyl alcohol and 2-ethynylbenzylamine derivatives promoted by TBAF was investigated. Six-membered ring derivatives were obtained from the compounds, which have abutyl group on the triple bond. Whereas five-membered ring products were afforded from the substrates having hydrogen or aromatic substituents. on the acetylene moiety. It was also concluded that both the tetrabutylammonium cation and fluoride anion were essential for the cyclization. Thus, the actual mechanism and catalytic cycle were also suggested. (C) 2001 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 08/08/20 alle ore 08:57:28