Polycyclic N-heterocyclic compounds.: 57 Syntheses of fused furo(or thieno)[2,3-b]pyridine derivatives via smiles rearrangement and cyclization

被引：19

作者：

Hirota, T

Tomita, K

Sasaki, K

Okuda, K

Yoshida, M

Kashino, S

机构：

[1] Okayama Univ, Fac Pharmaceut Sci, Okayama 7008530, Japan

[2] Okayama Univ, Fac Sci, Okayama 7008530, Japan

来源：

HETEROCYCLES | 2001年 / 55卷 / 04期

关键词：

D O I：

10.3987/COM-01-9168

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient methodology for the synthesis of thieno[2,3-c][2,7] naphthyridine (6), thieno[2,3-c]isoquinoline (11), furo[2,3-c]isoquinoline (14), [1]benzothieno[3,2-d]thieno[2,3-b]pyridine (21), and [1]benzothieno[3,2-d]furo-2,3-b]pyridine (26) skeletons from 4-[o-cyanoarylthio(or oxy)]butyronitriles with base via Smiles type rearrangement reaction followed by the cyclization is described.

引用

收藏

页码：741 / 752

页数：12

相关论文

共 14 条

[1] THE SYNTHESIS OF 1-2-DIHYDRO-1-OXO-5'-PHENYLFURANO-(2'3'-3-4)ISOQUINOLINE [J].

BAILEY, AS ;

SWALLOW, DL .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (JUL) :2477-2482

[2] MERCAPTOPYRIDINECARBOXYLIC ACIDS, SYNTHESIS AND HYPOGLYCEMIC ACTIVITY [J].

BLANK, B ;

DITULLIO, NW ;

MIAO, CK ;

OWINGS, FF ;

GLEASON, JG ;

ROSS, ST ;

BERKOFF, CE ;

SAUNDERS, HL ;

DELARGE, J ;

LAPIERE, CL .

JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (10) :1065-1071

[3] INHIBITION OF E-SELECTIN-MEDIATED, ICAM-1-MEDIATED, AND VCAM-1-MEDIATED CELL-ADHESION BY BENZO[B]THIOPHENE-CARBOXAMIDES, BENZOFURAN-CARBOXAMIDES, INDOLE-, AND NAPHTHALENE-2-CARBOXAMIDES - IDENTIFICATION OF PD-144795 AS AN ANTIINFLAMMATORY AGENT [J].

BOSCHELLI, DH ;

KRAMER, JB ;

KHATANA, SS ;

SORENSON, RJ ;

CONNOR, DT ;

FERIN, MA ;

WRIGHT, CD ;

LESCH, ME ;

IMRE, K ;

OKONKWO, GC ;

SCHRIER, DJ ;

CONROY, MC ;

FERGUSON, E ;

WOELLE, J ;

SAXENA, U .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (22) :4597-4614

[4]

Delarge J, 1967, J Pharm Belg, V22, P257

[5]

HARIGAYA Y, 1980, CHEM PHARM BULL, V28, P2029

[6] OXIDATIONS BY THIONYL CHLORIDE .6. MECHANISM OF REACTION WITH CINNAMIC ACIDS [J].

HIGA, T ;

KRUBSACK, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (21) :3037-3045

[7] POLYCYCLIC N-HETEROCYCLIC COMPOUNDS .49. NEW SYNTHETIC METHOD OF FURO[3,2-F][1,7]NAPHTHYRIDINE SKELETON [J].

HIROTA, T ;

MATSUSHITA, T ;

SASAKI, K ;

KASHINO, S .

HETEROCYCLES, 1995, 41 (11) :2565-2574

[8] STUDIES ON HETEROCYCLIC-COMPOUNDS .39. SYNTHESIS OF FURO[2,3-C]ISOQUINOLINE DERIVATIVES [J].

ITO, K ;

YAKUSHIJIN, K ;

YOSHINA, S ;

TANAKA, A ;

YAMAMOTO, K .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1978, 15 (02) :301-305

[9] HYDRAZINE DERIVATIVES .2. ORTHO-MERCAPTOPYRIDINECARBOHYDRAZIDES [J].

KATZ, L ;

SCHROEDER, W ;

COHEN, M .

JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (05) :711-717

[10] Polycyclic N-heterocyclic compounds .48. Syntheses of furo[2,3-h][1,6]naphthyridine and imidazo(or pyrimido)[2,1-f][1,6]naphthyridines with rearrangement [J].

Sasaki, K ;

Rouf, ASS ;

Hirota, T .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (01) :49-52