p-methoxybenzyl group as a protecting group of the nitrogen in indole derivatives: Deprotection by DDQ or trifluoroacetic acid

被引：24

作者：

Miki, Y ^{[1
]}

Hachiken, H ^{[1
]}

Kashima, Y ^{[1
]}

Sugimura, W ^{[1
]}

Yanase, N ^{[1
]}

机构：

[1] Kinki Univ, Fac Pharmaceut Sci, Higashiosaka, Osaka 577, Japan

来源：

HETEROCYCLES | 1998年 / 48卷 / 01期

关键词：

D O I：

10.3987/COM-97-7990

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deprotection of 9-p-methoxybenzylcarbazole with DDQ gave a carbazole. However, methyl 1-p-methoxybenzylindole-2-carboxylate and dimethyl 1-p-methoxybenzyl-2,3-indoledicarboxylate were treated with TFA to yield the corresponding methyl indole-2-carboxylate and dimethyl indole-2,3-dicarboxylate.

引用

页码：1 / 4

页数：4

共 50 条

[31] BORIC ACID DERIVATIVES AS REAGENTS IN CARBOHYDRATE CHEMISTRY .6. PHENYLBORONIC ACID AS A PROTECTING GROUP IN DISACCHARIDE SYNTHESIS
FERRIER, RJ
PRASAD, D
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (DEC): : 7429 - &
[32] SOLUTION-PHASE SYNTHESIS OF AN ANTI-HUMAN-IMMUNODEFICIENCY-VIRUS PEPTIDE, T22 ([TYR(5,12),LYS(7)]-POLYPHEMUSIN-II), AND THE MODIFICATION OF TRP BY THE P-METHOXYBENZYL GROUP OF CYS DURING TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE DEPROTECTION
TAMAMURA, H
OTAKA, A
TAKADA, W
TERAKAWA, Y
YOSHIZAWA, H
MASUDA, M
IBUKA, T
MURAKAMI, T
NAKASHIMA, H
WAKI, M
MATSUMOTO, A
YAMAMOTO, N
FUJII, N
CHEMICAL & PHARMACEUTICAL BULLETIN, 1995, 43 (01) : 12 - 18
[33] Regiodivergent cascade cyclization/alkoxylation of allenamides via N-protecting group driven rearrangement to access indole and indoline derivatives
Chaudhary, Dhananjay
Yadav, Suman
Maurya, Naveen Kumar
Kumar, Dharmendra
Ishu, Km
Kuram, Malleswara Rao
CHEMICAL COMMUNICATIONS, 2022, 58 (80) : 11300 - 11303
[34] Oxidative removal of p-methoxybenzyl-amino protecting group in the presence of a proximal hydroxy function:: A solution to a process problem in SUSTIVA® (efavirenz) synthesis
Choudhury, A
Pierce, ME
Confalone, PN
SYNTHETIC COMMUNICATIONS, 2001, 31 (23) : 3707 - 3714
[35] NITRILE GROUP IN PEPTIDE CHEMISTRY .9. USE OF TERT-BUTYLOXYCARBONYL PROTECTING GROUP FOR PREPARATION OF AMINO ACID NITRILES AND THEIR PEPTIDE DERIVATIVES
GRZONKA, Z
LIBEREK, B
BULLETIN DE L ACADEMIE POLONAISE DES SCIENCES-SERIE DES SCIENCES BIOLOGIQUES, 1969, 17 (04): : 219 - &
[36] SOLID-PHASE PEPTIDE-SYNTHESIS - STUDY ON EFFECT OF TRIFLUOROACETIC-ACID CONCENTRATION ON REMOVAL OF TERT-BUTYLOXYCARBONYL PROTECTING GROUP
REID, RE
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (06): : 1027 - 1031
[37] 5-FLUOROURACIL DERIVATIVES .21. A SYNTHESIS OF 5'-O-ACRYLOYL-5-FLUOROURIDINE BY USE OF PARA-METHOXYBENZYL GROUP AS AN N-3-IMIDE PROTECTING GROUP OF 5-FLUOROURIDINE
AKIYAMA, T
TAKESUE, Y
KUMEGAWA, M
NISHIMOTO, H
OZAKI, S
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (07) : 2266 - 2269
[38] Scope and Limitations of Barbituric and Thiobarbituric Amino Acid Derivatives as Protecting Groups for Solid-Phase Peptide Synthesis: Towards a Green Protecting Group
Ramkisson, Shaveer
Al-Rasheed, Hessa H.
Dahlous, Kholood A.
De La Torre, Beatriz G.
El-Faham, Ayman
Albericio, Fernando
CHEMISTRYSELECT, 2021, 6 (26): : 6626 - 6630
[39] NEW CLASS OF DISULFIDE-CONTAINING AMINO-ACID DERIVATIVES - APPLICATION AS A PROTECTING GROUP FOR PEPTIDE-SYNTHESIS
BARANY, G
MERRIFIELD, RB
FEDERATION PROCEEDINGS, 1977, 36 (03) : 864 - 864
[40] REVERSIBLE MODIFICATION OF THE ACID-LABILE 2-HYDROXY-4-METHOXYBENZYL (HMB) AMIDE PROTECTING GROUP - A SIMPLE SCHEME YIELDING BACKBONE SUBSTITUTED FREE PEPTIDES
QUIBELL, M
TURNELL, WG
JOHNSON, T
TETRAHEDRON LETTERS, 1994, 35 (14) : 2237 - 2238

← 1 2 3 4 5 →