Intramolecular cyclization of acyl radicals onto the azido group: A new radical approach to cyclized lactams

被引：58

作者：

Benati, L ^{[1
]}

Leardini, R ^{[1
]}

Minozzi, M ^{[1
]}

Nanni, D ^{[1
]}

Spagnolo, P ^{[1
]}

Strazzari, S ^{[1
]}

Zanardi, G ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 18期

关键词：

D O I：

10.1021/ol026366t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

([)GRAPHICS] Aryl- and alkyl-derived azidoacyl radicals, generated from thiolesters by intramolecular homolytic substitution at the sulfur, can undergo five-and six-membered cyclization onto the azido moiety to give cyclized lactams.

引用

页码：3079 / 3081

页数：3

共 50 条

[31] MN(III) - PROMOTED CYCLIZATION OF ENAMIDES - AN OXIDATIVE RADICAL APPROACH TO BETA-LACTAMS
DANNIBALE, A
RESTA, S
TROGOLO, C
TETRAHEDRON LETTERS, 1995, 36 (49) : 9039 - 9042
[32] Photocatalytic intramolecular radical cyclization involved synergistic SET and HAT: synthesis of 3,3-difluoro-γ-lactams
Zhuang, Xiaohui
Shi, Xiayue
Zhu, Rui
Sun, Bin
Su, WeiKe
Jin, Can
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (04): : 736 - 742
[33] Selective 6-endo cyclization of the acyl radicals onto the nitrogen of imine and oxazoline C - N bonds
Tojino, Mami
Otsuka, Noboru
Fukuyama, Takahide
Matsubara, Hiroshi
Ryu, Ulhyong
Journal of the American Chemical Society, 2006, 128 (24): : 7712 - 7713
[34] PHOTOINDUCED FREE-RADICAL CHEMISTRY OF THE ACYL TELLURIDES - GENERATION, INTERMOLECULAR AND INTRAMOLECULAR TRAPPING, AND ESR SPECTROSCOPIC IDENTIFICATION OF ACYL RADICALS
CRICH, D
CHEN, C
HWANG, JT
YUAN, HW
PAPADATOS, A
WALTER, RI
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) : 8937 - 8951
[35] SYNTHESIS OF NEW RACEMIC BICYCLIC GAMMA-LACTAMS AND DELTA-LACTAMS BASED ON 2-FOLD INTRAMOLECULAR CYCLIZATION
TAO, EV
BRENNAN, J
SWARTZENDRUBER, JK
DEETER, JB
HETEROCYCLES, 1989, 29 (01) : 133 - 140
[36] Diastereoselective Cyclization of 1,3-Dioxan-2-yl Radicals: Chiral Acyl Radical Equivalents
Bertrand, M. P.
Crich, D.
Nouguire, R.
Samy, R.
Journal of Organic Chemistry, 61 (11):
[37] A new entry to α-alkylidene-β-lactams by 4-exo-dig cyclization of carbamoyl radicals
Fujiwara, Shin-ichi
Shimizu, Yoshihiko
Imahori, Yuji
Toyofuku, Masashi
Shin-ike, Tsutomu
Kambe, Nobuaki
TETRAHEDRON LETTERS, 2009, 50 (26) : 3628 - 3630
[38] A NEW EXAMPLE OF DIMROTH-REARRANGEMENT - INTRAMOLECULAR CYCLIZATION OF ACYL DERIVATIVES OF ANTHRANYL NITRILE
ABBAKUMOVA, NV
PUTSYKIN, YG
BASKAKOV, YA
KONDRATYEV, YA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1981, (09): : 1264 - 1266
[39] Radical cyclization of thio- and seleno-esters - An intramolecular acylation approach
Kim, SG
Jon, SY
CHEMICAL COMMUNICATIONS, 1996, (11) : 1335 - 1336
[40] Vinyl radical cyclization onto imino group. Selective 6-endo cyclization onto aldimines leading to 3-methylenepiperidines
Ryu, I
Ogura, S
Minakata, S
Komatsu, M
TETRAHEDRON LETTERS, 1999, 40 (08) : 1515 - 1518

← 1 2 3 4 5 →