One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds

被引：12

作者：

Filippov, Ilya P. ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

Khlebnikov, Alexander F. ^{[1
]}

Rostovskii, Nikolai V. ^{[1
]}

机构：

[1] St Petersburg State Univ, Inst Chem, St Petersburg 199034, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 13期

基金：

俄罗斯科学基金会;

关键词：

ENANTIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; RING-CLOSURE; DERIVATIVES; HETEROCYCLES; 2H-PYRROLES; CYCLIZATION; ANNULATION; PYRROLES; MICHAEL;

D O I：

10.1021/acs.joc.2c00977

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel strategy for the synthesis of 1-pyrrolines based on formal [4 + 1] annulation of 2-alkyl-2H-azirines with diazocarbonyl compounds has been developed. This one-pot approach includes the Rh(II)-catalyzed formation of 4-alkyl-2-azabuta-1,3-dienes, followed by the DBU-promoted cyclization, and features a good substrate tolerance. The 1-pyrrolines containing an ester group at the C3 were prepared in a three-step one-pot procedure starting from 5-alkoxyisoxazoles. The cyclization of 2-azabutadienes to 1-pyrrolines most likely proceeds via the 6 pi electrocyclization of a conjugated NH-azomethine ylide.

引用

页码：8835 / 8840

页数：6

共 50 条

[31] One-pot synthesis of alkyl 3-aryl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)propanoates
N. T. Pokhodylo
R. D. Savka
M. D. Obushak
Russian Journal of Organic Chemistry, 2017, 53 : 734 - 737
[32] One-pot synthesis of 2-(1-alkyl/aralkyl-1H-benzimidazole-2-yl)-quinoxaline derivatives using molecular iodine
Dubey, P. K.
Reddy, P. V. V. Prasada
Srinivas, K.
SYNTHETIC COMMUNICATIONS, 2008, 38 (04) : 613 - 618
[33] One-pot synthesis of alkyl 3-aryl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)propanoates
Pokhodylo, N. T.
Savka, R. D.
Obushak, M. D.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 53 (05) : 734 - 737
[34] A one-pot Synthesis of Functionalized Azadienes from 2-hydroxypyridine, Activated Acetylenes and Alkyl Isocyanides
Ghasemi, Elnaz
Yavari, Issa
ORIENTAL JOURNAL OF CHEMISTRY, 2015, 31 (04) : 2125 - 2128
[35] ONE-POT SYNTHESIS OF 1-PHENYLSULFONYL-2-AROYLINDOLES
Dhayalan, Vasudevan
Panchapakesan, Ganapathy
Mohanakrishnan, Arasambattu K.
SYNTHETIC COMMUNICATIONS, 2012, 42 (03) : 402 - 411
[36] One-pot synthesis of alkyl pyrrole-2-carboxylates starting from β-nitroacrylates and primary amines
Palmieri, Alessandro
Gabrielli, Serena
Parlapiano, Marco
Ballini, Roberto
RSC ADVANCES, 2015, 5 (06): : 4210 - 4213
[37] One-pot synthesis of 1,2,4-triazines
Rostamizadeh, S
Sadeghi, K
SYNTHETIC COMMUNICATIONS, 2002, 32 (12) : 1899 - 1902
[38] ONE-POT SYNTHESIS OF 2-ALKYLAMINO-4-OXO-4H-3, 1-BENZOXAZINES FROM ANTHRANILIC ACIDS AND ALKYL ISOCYANATES
KOEDJIKOV, AH
BLAGOEVA, IB
POJARLIEFF, IG
DOKLADI NA BOLGARSKATA AKADEMIYA NA NAUKITE, 1984, 37 (06): : 765 - 766
[39] A ONE-POT SYNTHESIS OF AZIRIDINES FROM 2-AMINOETHANOLS
PFISTER, JR
SYNTHESIS-STUTTGART, 1984, (11): : 969 - 970
[40] One-pot synthesis of 2-alkyl cycloketones on bifunctional Pd/ZrO2 catalyst
Xue, Weiyang
Gu, Bin
Wu, Huiling
Liu, Mengyang
He, Songbo
Li, Jingmei
Rong, Xin
Sun, Chenglin
APPLIED CATALYSIS A-GENERAL, 2021, 616 (616)

← 1 2 3 4 5 →