Synthesis of Triazolo[4′,5′:4,5]furo[2,3-c]pyridine via Post Modification of an Unusual Groebke-Blackburn-Bienayme Multicomponent Reaction

被引：0

作者：

Batra, Aashima ^{[1
,2
]}

Kaur, Manpreet ^{[1
,2
]}

Kaushik, Deepender ^{[1
,2
]}

Kaur, Simran ^{[3
]}

Patil, Madhuri T. ^{[4
]}

Chaudhari, Vinod D. ^{[3
]}

Sahoo, Subash Chandra ^{[1
,2
]}

Salunke, Deepak B. ^{[1
,2
,5
]}

机构：

[1] Panjab Univ, Dept Chem, Chandigarh 160014, India

[2] Panjab Univ, Ctr Adv Studies, Chandigarh 160014, India

[3] CSIR Inst Microbial Technol, Div Med Chem, Chandigarh 160036, India

[4] Mehr Chand Mahajan DAV Coll Women, Chandigarh 160036, India

[5] Panjab Univ, Natl Interdisciplinary Ctr Vaccines Immunotherapeu, Chandigarh 160014, India

来源：

ACS OMEGA | 2024年

关键词：

STRUCTURAL MODIFICATION; PYRAZINES;

D O I：

10.1021/acsomega.4c01359

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Groebke-Blackburn-Bienayme (GBB) reaction is a well-established three-component reaction for synthesizing imidazofused scaffolds from heterocyclic amidines, aldehydes, and isonitriles. However, the replacement of pyridoxal as an aldehyde component in this reaction results in the formation of the furo[2,3-c]pyridine skeleton as an "unusual GBB product". Despite the interesting nature of this unusual reaction, not much work was further reported. The present research investigates the optimization strategy for the synthesis of novel tricyclic triazolo[4 ',5 ':4,5]furo[2,3-c]pyridines via diazotization of 2,3-diamino-furo[2,3-c]pyridines specifically synthesized utilizing the chemistry of tert-alkyl isocyanide.

引用

页码：29372 / 29378

页数：7

共 5 条

[1] Synthesis of novel imidazo[1,2-a]pyridine-4-hydroxy-2H-coumarins by Groebke-Blackburn-Bienayme multicomponent reaction as potential NS5B inhibitors
Manvar, Parth
Shaikh, Faraz
Kakadiya, Rajesh
Mehariya, Krunal
Khunt, Ranjan
Pandey, Bipin
Shah, Anamik
TETRAHEDRON, 2016, 72 (10) : 1293 - 1300
[2] Fast Assembly of 1H-Imidazo[1,2-a]imidazol-5-amines via Groebke-Blackburn-Bienayme Reaction with 2-Aminoimidazoles
Pereshivko, Olga P.
Peshkov, Vsevolod A.
Ermolat'ev, Denis S.
Van der Eycken, Erik V.
SYNLETT, 2013, 24 (03) : 351 - 354
[3] One-Pot Synthesis of 1,2,3-Triazol-4-linked benzo[d]imidazo[1,2-a]imidazol-3-amines via Sequential Groebke-Blackburn-Bienayme/Click Reaction
Moghanlou, Mohammad
Mirza, Behrooz
POLYCYCLIC AROMATIC COMPOUNDS, 2020, 40 (04) : 1036 - 1044
[4] Synthesis of [1,2,4,5]tetrazino[6′,1′:2,3]imidazo[4,5-c]isoquinolin-5-ones by microwave-assisted three-component reaction
Pellegatti, Laurent
Vedrenne, Emeline
Hiebel, Marie-Aude
Buron, Frederic
Massip, Stephane
Leger, Jean-Michel
Jarry, Christian
Routier, Sylvain
TETRAHEDRON LETTERS, 2011, 52 (41) : 5224 - 5228
[5] Synthesis of novel dihydropyridine, fused dihydropyridines, hexahydrobenzo[4,5]imidazo[2,1-b]quinazolines, and fused-pyrans linked to piprazine core via benzoyloxyacetyl likages as new hybrid molecules utilizing Michael, and Hantzsch reaction
Hammad, Hadeel F.
Darweesh, Ahmed F.
Abdelaziz, Mahfouz A.
Elwahy, Ahmed H. M.
Abdelhamid, Ismail A.
SYNTHETIC COMMUNICATIONS, 2023, 53 (16) : 1305 - 1318

← 1 →