TY - JOUR
T1 - Syntheses of Iso‐Condensed Heteroaromatic Pyrroles
AU - Sha, Chin‐Kang ‐K
AU - Tsou, Chiu‐Peng ‐P
AU - Tsai, Chung‐Yin ‐Y
AU - Liu, Jia‐Ming ‐M
AU - Lee, Ren‐Sheng ‐S
AU - Li, Yu‐Chang ‐C
AU - Tsai, Fu‐Yuan ‐Y
AU - Way, Shiow‐Jye ‐J
AU - Young, Jenn‐Jong ‐J
AU - Chuan, Kuang‐Sein ‐S
AU - Yeh, Ren‐Hwa ‐H
PY - 1992/12
Y1 - 1992/12
N2 - Three novel reactions for the synthesis of iso‐condensed heteroaromatic pyrroles: (1) tandem intramolecular 1,3‐dipolar cycloaddition and cycloreversion reaction; (2) phosphineimine‐alkylidenemalonate cyclization reaction; (3) retromalonate addition reaction, are described. They can be used in acidic, neutral or basic conditions respectively. Iso‐condensed heteroaromatic pyrroles, such as pyrrolo[3,4‐b]indole 12, pyrrolo[3,4‐b]pyridine 17, pyrrolo[3,4‐c]pyridine 18, thieno[2,3‐c]pyrrole 37, pyrrolo[3,4‐b]pyrrole 40, pyrrolo[3,4‐b]pyrazine 49, benzofuro[2,3‐c]pyrrole 50, 1,2‐bis[5‐thieno[2,3‐c]pyrrolyl]ethane 51, 1,4‐bis[5‐thieno[2,3‐c]pyrrolyl]benzene 52, dipyrrolo[3,4‐b;3′,4′‐d]dipyrroles 55 and 56, benzotripyrroles 62–64, and thieno[3,4‐c]pyrroles 67 and 73 are synthesized efficiently according to these methods.
AB - Three novel reactions for the synthesis of iso‐condensed heteroaromatic pyrroles: (1) tandem intramolecular 1,3‐dipolar cycloaddition and cycloreversion reaction; (2) phosphineimine‐alkylidenemalonate cyclization reaction; (3) retromalonate addition reaction, are described. They can be used in acidic, neutral or basic conditions respectively. Iso‐condensed heteroaromatic pyrroles, such as pyrrolo[3,4‐b]indole 12, pyrrolo[3,4‐b]pyridine 17, pyrrolo[3,4‐c]pyridine 18, thieno[2,3‐c]pyrrole 37, pyrrolo[3,4‐b]pyrrole 40, pyrrolo[3,4‐b]pyrazine 49, benzofuro[2,3‐c]pyrrole 50, 1,2‐bis[5‐thieno[2,3‐c]pyrrolyl]ethane 51, 1,4‐bis[5‐thieno[2,3‐c]pyrrolyl]benzene 52, dipyrrolo[3,4‐b;3′,4′‐d]dipyrroles 55 and 56, benzotripyrroles 62–64, and thieno[3,4‐c]pyrroles 67 and 73 are synthesized efficiently according to these methods.
KW - 5H‐thieno[2,3‐c]pyrrole
KW - Benzotripyrrole
KW - Bis[thieno[2,3‐c]pyrrole]
KW - Dipyrrolo[3,4‐b:3′,4′‐d]pyrrole
KW - Pyrrolo[3,4‐b] pyridine
KW - Pyrrolo[3,4‐b]indole
KW - Pyrrolo[3,4‐b]pyrrole
KW - Pyrrolo[3,4‐c)pyridine
KW - Thieno[3,4‐c]pyrrole
UR - https://www.scopus.com/pages/publications/84986435714
U2 - 10.1002/jccs.199200098
DO - 10.1002/jccs.199200098
M3 - 文章
AN - SCOPUS:84986435714
SN - 0009-4536
VL - 39
SP - 635
EP - 639
JO - Journal of the Chinese Chemical Society
JF - Journal of the Chinese Chemical Society
IS - 6
ER -