(C6F5)3B Catalyzed One-Pot Synthesis of Benzo[b]Cyclopenta[e][1,4]Oxazin-2(1H)-One and Thiazin-2(1H)-One Derivatives from Furan-2-yl(Phenyl)Methanol and 2-Aminophenol/Thiophenol

被引：0

作者：

Sarnikar, Yuvaraj P. ^{[1
]}

Mane, Yogesh D. ^{[2
]}

Patil, Smita S. ^{[1
]}

Surwase, Santosh M. ^{[3
]}

Tigote, Radhakrishnan M. ^{[4
]}

Khade, Bhimrao C. ^{[5
]}

机构：

[1] Dayanand Sci Coll, Dept Chem, Latur, India

[2] BSS Arts Sci & Commerce Coll, Dept Chem, Makni, India

[3] Shri Chhatrapati Shivaji Coll, Dept Chem, Omerga, India

[4] Dr BAM Univ, Dept Chem, Osmanabad, India

[5] Coll Arts Commerce & Sci, Dept Chem, Parbhani, Maharashtra, India

来源：

POLYCYCLIC AROMATIC COMPOUNDS | 2023年 / 43卷 / 05期

关键词：

Benzo[b][1; 4]oxazine; 4]thiazine; Tris(pentafluorophenyl)Borane (BCF); Piancatelli rearrangement; 1,4-BENZOXAZINE DERIVATIVES; ORGANIC-SYNTHESIS; TRIS(PENTAFLUOROPHENYL)BORANE; REAGENTS; FACILE;

D O I：

10.1080/10406638.2022.2089173

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient (C6F5)(3)B catalyzed method has been developed for the synthesis of benzo[b]cyclopenta[e][1,4]oxazin-2(1H)-one and thiazin-2(1H)-one derivatives from furan-2-yl(phenyl)methanol (1) and 2-aminophenol/thiophenol (2) under reflux in acetonitrile. This reaction proceeds through an aza-Piancatelli rearrangement/Michael reaction in one-pot. This strategy provides a facile and rapid access to benzo[b]cyclopenta[e][1,4]oxazin-2(1H)-one and thiazin-2(1H)-one derivatives (3a-l) in good to high yields under mild conditions. Several advantages, such as simple reaction procedure, low catalyst loading, broad substrate scope, easy product isolation, high functional group tolerance, and short reaction time make this strategy more attractive.

引用

页码：4313 / 4321

页数：9

共 50 条

[1] One-pot B(C6F5)3 catalyzed cascade synthesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-ones
Shinde, Achut R.
Mane, Yogesh D.
Muley, Dnyanoba B.
SYNTHETIC COMMUNICATIONS, 2020, 50 (01) : 33 - 40
[2] A metal catalyst-free and one-pot synthesis of (3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methanol derivatives in water
Singh, Shambhu Nath
Jayaprakash, Sarva
Reddy, K. Venkateshwara
Nakhi, Ali
Pal, Manojit
RSC ADVANCES, 2015, 5 (103): : 84889 - 84893
[3] SYNTHESIS OF CYCLIC HYDROXAMIC ACIDS DERIVED FROM THE STRUCTURE OF 1-HYDROXY-PYRIDO[2,3-B][1,4]OXAZIN-2(1H)-ONE
HEILMANN, D
SICKER, D
JOURNAL FUR PRAKTISCHE CHEMIE, 1990, 332 (02): : 265 - 268
[4] Synthesis of (1H)-3,4-Dihydropyrrolo[2,1-c][1,4]oxazin-1-one Derivatives
De Cai FU
Chinese Chemical Letters, 2002, (11) : 1051 - 1054
[5] Synthesis of (1H)-3,4-dihydropyrrolo[2,1-c][1,4]oxazin-1-one derivatives
Fu, DC
Yu, H
Zhang, SF
CHINESE CHEMICAL LETTERS, 2002, 13 (11) : 1051 - 1054
[6] Synthesis of 3-Aminopyridin-2(1H)-Ones and 1H-Pyrido[2,3-b][1,4]Oxazin-2(3H)-Ones
A. S. Fisyuk
I. V. Kulakov
D. S. Goncharov
O. S. Nikitina
Y. P. Bogza
A. L. Shatsauskas
Chemistry of Heterocyclic Compounds, 2014, 50 : 217 - 224
[7] Synthesis of 3-Aminopyridin-2(1H)-Ones and 1H-Pyrido[2,3-b][1,4]Oxazin-2(3H)-Ones
Fisyuk, A. S.
Kulakov, I. V.
Goncharov, D. S.
Nikitina, O. S.
Bogza, Y. P.
Shatsauskas, A. L.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (02) : 217 - 224
[8] Synthesis of 3-aminopyridin-2(1H)-ones and 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones
Fisyuk, A.S. (fisyuk@chemomsu.ru), 1600, Springer Science and Business Media, LLC (50):
[9] One-pot Synthesis of 1,2,3,4-Tetrahydropyrimidin-2(1H)-thione Derivatives and their Biological Activity
Salem, Mounir A. I.
Marzouk, Magda I.
Salem, Marwa S.
Alshibani, Ghazala A.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (02) : 545 - 557
[10] Synthesis of 2-Phenyl-2-benzoylquinazolin-4(1H)-one Derivatives in Ionic Liquids Catalyzed by Iodine
Zhang, Meimei
Liu, Yun
Wang, Xiangshan
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (08) : 1682 - 1686

← 1 2 3 4 5 →