N-heterocycle-Triggered MCRs: An approach to the concise synthesis of perfluoroalkylated spiro-1,3-oxazines

Gang Liu; Yueci Wu; Jing Han; Weimin He; Jie Chen; Hongmei Deng; Min Shao; Hui Zhang; Weiguo Cao

doi:10.1055/s-0037-1609563

N-heterocycle-Triggered MCRs: An approach to the concise synthesis of perfluoroalkylated spiro-1,3-oxazines

Gang Liu
, Yueci Wu
, Jing Han
, Weimin He
, Jie Chen
, Hongmei Deng
, Min Shao
, Hui Zhang
, Weiguo Cao

Shanghai University
CAS - Shanghai Institute of Organic Chemistry

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

Multicomponent reactions involving methyl perfluoroalk-2-ynoates initiated by N-heterocycles (quinoline, isoquinoline, and benzothiazole) in the presence of isatins and diaryl 1,2-diketones allowed efficient access to trifluoromethyl-or other perfluoroalkyl-substituted spiro-1,3-oxazine derivatives. This facile transformation is regioselective and proceeded smoothly through a 1,4-dipolar intermediate under mild conditions, affording the products in good to excellent yields.

Original language	English
Pages (from-to)	4668-4682
Number of pages	15
Journal	Synthesis (Germany)
Volume	50
Issue number	23
DOIs	https://doi.org/10.1055/s-0037-1609563
Publication status	Published - 8 Aug 2018
Externally published	Yes

Keywords

1
4-dipole
multicomponent reaction (MCR)
N-heterocycle
Perfluoroalkyl-substituted
Spiro-oxazino derivatives

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10.1055/s-0037-1609563

Cite this

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title = "N-heterocycle-Triggered MCRs: An approach to the concise synthesis of perfluoroalkylated spiro-1,3-oxazines",

abstract = "Multicomponent reactions involving methyl perfluoroalk-2-ynoates initiated by N-heterocycles (quinoline, isoquinoline, and benzothiazole) in the presence of isatins and diaryl 1,2-diketones allowed efficient access to trifluoromethyl-or other perfluoroalkyl-substituted spiro-1,3-oxazine derivatives. This facile transformation is regioselective and proceeded smoothly through a 1,4-dipolar intermediate under mild conditions, affording the products in good to excellent yields.",

keywords = "1, 4-dipole, multicomponent reaction (MCR), N-heterocycle, Perfluoroalkyl-substituted, Spiro-oxazino derivatives",

author = "Gang Liu and Yueci Wu and Jing Han and Weimin He and Jie Chen and Hongmei Deng and Min Shao and Hui Zhang and Weiguo Cao",

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TY - JOUR

T1 - N-heterocycle-Triggered MCRs

T2 - An approach to the concise synthesis of perfluoroalkylated spiro-1,3-oxazines

AU - Liu, Gang

AU - Wu, Yueci

AU - Han, Jing

AU - He, Weimin

AU - Chen, Jie

AU - Deng, Hongmei

AU - Shao, Min

AU - Zhang, Hui

AU - Cao, Weiguo

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart.

PY - 2018/8/8

Y1 - 2018/8/8

N2 - Multicomponent reactions involving methyl perfluoroalk-2-ynoates initiated by N-heterocycles (quinoline, isoquinoline, and benzothiazole) in the presence of isatins and diaryl 1,2-diketones allowed efficient access to trifluoromethyl-or other perfluoroalkyl-substituted spiro-1,3-oxazine derivatives. This facile transformation is regioselective and proceeded smoothly through a 1,4-dipolar intermediate under mild conditions, affording the products in good to excellent yields.

AB - Multicomponent reactions involving methyl perfluoroalk-2-ynoates initiated by N-heterocycles (quinoline, isoquinoline, and benzothiazole) in the presence of isatins and diaryl 1,2-diketones allowed efficient access to trifluoromethyl-or other perfluoroalkyl-substituted spiro-1,3-oxazine derivatives. This facile transformation is regioselective and proceeded smoothly through a 1,4-dipolar intermediate under mild conditions, affording the products in good to excellent yields.

KW - 1

KW - 4-dipole

KW - multicomponent reaction (MCR)

KW - N-heterocycle

KW - Perfluoroalkyl-substituted

KW - Spiro-oxazino derivatives

U2 - 10.1055/s-0037-1609563

DO - 10.1055/s-0037-1609563

M3 - Article

AN - SCOPUS:85054434684

SN - 0039-7881

VL - 50

SP - 4668

EP - 4682

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 23

ER -

N-heterocycle-Triggered MCRs: An approach to the concise synthesis of perfluoroalkylated spiro-1,3-oxazines

Abstract

Keywords

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